Venues

Blenheim Vineyards

Blenheim Vineyards is a family-owned winery located about 20 minutes from downtown Charlottesville, Virginia, set in a scenic, rustic landscape of rolling hills and grapevines. The winery farms several distinct vineyard sites, including its Blenheim, Claim, Deer Ridge, and Seaview vineyards, each with its own terroir and soils, and takes a minimalist, sustainable approach in the cellar to let the fruit speak for itself under winemaker Kirsty Harmon. Visitors are welcome in the tasting room, a warm wooden space with vaulted ceilings and large windows overlooking the vineyard, where they can sample Virginia-grown wines; reservations are not required, though guided tastings are recommended on Saturdays. The winery is known for its annual Painted Series, a pair of limited-edition red and white wines whose labels are created or curated by musician Dave Matthews. Blenheim also offers a wine club with three releases per year and a calendar of tastings and events throughout the season.

Outdoor SeatingPicnic

• Meet the Artist: Richard WhiteSun, Jul 26, 2026, 2 PM – 4 PM
• Field Day: Susie & The PistolsSun, Aug 2, 2026, 3 PM – 5 PM
• Meet the Artist: Nicole SingletonSun, Aug 30, 2026, 2 PM – 4 PM

+ 5 more upcoming events →

Chisholm Vineyards

Chisholm Vineyards is a family-owned, woman-owned and operated winery located on Adventure Farm near Charlottesville, Virginia, within the Monticello AVA, where the Chisholm family has owned and worked the 500-acre property since 1950. The winery produces 100 percent estate-grown Virginia wine, crafting small-lot, award-winning bottlings in a low-intervention style that lets the grape, terroir, and climate define each unique vintage. Visitors can settle into a variety of settings, from the tasting room to an outdoor pavilion, a wisteria arbor, or expansive lawns framed by Blue Ridge Mountain views, and the property is both child- and dog-friendly. Wines are available on-site, by curbside pickup, and via shipping to many states, and the winery offers a no-fee wine club with member discounts, exclusive events, and perks. The grounds also serve as an event venue for weddings, rehearsal dinners, and private gatherings, and host a mobile Finnish wood-fired sauna and cold plunge experience for relaxation and celebrations.

DogsOutdoor SeatingB&B

• Sunset Soirée - Chickenhead Blues with Oyster Catcher Sea FarmsFri, Jul 17, 2026, 6 PM – 9 PM
• Sunday Session - The TrioSun, Jul 19, 2026, 1 PM – 4 PM
• Friday Sunset Soirée - Scuffletown with Twisted ProvisionsFri, Jul 24, 2026, 6 PM – 9 PM

+ 11 more upcoming events →

Eastwood Farm and Winery

Eastwood Farm and Winery is a women-owned, multi-generational winery and wine incubator located just five miles from downtown Charlottesville, Virginia, on the Monticello Wine Trail. Its tasting room sits in a peaceful country setting near the University of Virginia and Monticello, and the winery pours award-winning wines, including Governor's Cup gold medal winners, alongside housemade beers and ciders inspired by its seasonal farm. Guests can pair their wine with a full lunch and dinner menu created by the winery's chefs, and enjoy ample indoor and outdoor seating including a covered patio, with the winery open seven days a week and late on Thursday through Saturday. Eastwood is dog-friendly and family-friendly, offering non-alcoholic options such as popular juice flights, and it hosts live music and events throughout the week. The business also operates a second location, the Virginia Wine Collective, an urban wine production facility and tasting room about three miles away that serves thin-crust pizzas, shareable plates, winemaker flights, and beers on tap, and is open to guests 21 and over.

DogsFamily FriendlyOutdoor Seating

• Porch Nights: Jim RichardsonThu, Jul 16, 2026, 5 PM
• Live Music: Sue HarlowFri, Jul 17, 2026, 5 PM
• Live Music: FarAwaySat, Jul 18, 2026, 12:30 PM

+ 11 more upcoming events →

Hark Vineyards

Hark Vineyards is a family-owned winery in Virginia built on the belief that beautiful views and delicious wine can bring people together. The wines are authentically Virginian, produced on site from grapes grown on the estate, and visitors can see the production space directly from the tasting room. Set across an 80-acre estate, the winery invites guests to sample thoughtfully crafted small-batch wines that aim to stay true to vintage and terroir. Visitors can take in the scenic views, cozy up to a fire, and spend a relaxed afternoon in the tasting room. Hark has earned notable recognition, including being one of only two wineries to take home five Gold medals in the 2026 Virginia Governor's Cup for wines such as its Roussanne, Cabernet Franc, Petit Verdot, and estate blends Ember and Spark.

EV Charging

• Vincent Zorn MusicSat, Jul 18, 2026, 4 PM – 7 PM
• Sweet Jane's Kitchen & Matthew O'Donnell MusicSat, Jul 25, 2026, 10 AM
• Sue Harlow MusicSun, Jul 26, 2026, 3 PM – 6 PM

+ 3 more upcoming events →

Jefferson Vineyards

Jefferson Vineyards is a historic winery just 10 minutes from Charlottesville, set in the rolling foothills of the Blue Ridge Mountains at the heart of Virginia wine country. The site carries deep winemaking roots, as nearly 250 years ago Thomas Jefferson and Philip Mazzei began growing grapes on this very land in pursuit of Jefferson's dream of establishing American winemaking. The vineyard neighbors Monticello, Jefferson's mountaintop home, and Highland, the nearby estate of President James Monroe. Visitors can sample the winery's award-winning wines, which range from delicate and refreshing to elegant, full-bodied, and rich, in the tasting room open daily. Guests can also shop the wines, join a wine club, and soak in the scenery and history of one of Virginia's earliest wine sites.

DogsFamily FriendlyOutdoor Seating

• Live Music at Jefferson Vineyards: Melissa HansenFri, Jul 17, 2026, 5 PM – 7 PM
• Live Music at Jefferson Vineyards: Paxton HendersonSun, Jul 19, 2026, 2 PM – 4 PM
• Live Music at Jefferson Vineyards: Chris HammockFri, Jul 24, 2026, 5 PM – 7 PM

+ 33 more upcoming events →

Knights Gambit Vineyard

Knight's Gambit Vineyard is a family-run winery at 218 Knole Farm Lane in Charlottesville, Virginia, where guests come to enjoy estate-grown wines amid vineyard and mountain views. Visitors to the tasting room can sample a flight of all six estate-grown wines, or enjoy their favorites by the glass or bottle. The property features a furnished Cabana Deck, a semi-private micro venue with comfy couches, airy curtains, and seating for up to 20, available to rent for parties, day dates, and family gatherings. The winery also hosts live music and can accommodate weddings and larger private parties. Knight's Gambit is open Thursday through Sunday, with afternoon and evening hours that stretch later toward the weekend.

DogsWeddingsOutdoor Seating

No upcoming events listed.

Michael Shaps Wineworks

Michael Shaps Wineworks is a winery nestled in the woods just south of Charlottesville, Virginia, offering a tasting experience that blends Old World tradition with Virginia terroir. Founded in 2007 by acclaimed winemaker Michael Shaps, the winery is known for producing small-batch, age-worthy wines that emphasize balance, varietal integrity, and regional character. Guests can enjoy seated tastings featuring both the Michael Shaps Virginia wines and his imported Maison Shaps Burgundy selections, which are bottled in Meursault, France and shipped directly to the winery. The rustic-industrial tasting room provides ample indoor and outdoor seating, including a spacious deck, a stone patio, and an expansive front lawn for relaxed sipping in nature, while wine club members can retreat to the upstairs Loft for more intimate gatherings. With flights, glasses, and bottles to enjoy, a wine club offering curated Virginia and Burgundy shipments, and curated events throughout the year, Michael Shaps Wineworks celebrates craftsmanship and the evolving story of Virginia wine.

Outdoor Seating

No upcoming events listed.

Winery

Monte Piccolo Farm and Distillery

Monte Piccolo Farm and Distillery is a small farm-to-bottle distillery that grows its own fruit and distills it into fine spirits in a true organic operation. The distillery specializes in fresh fruit "eau de vie" style brandies, made from hand-harvested, tree-ripened fruit whose essences are captured in the glass through distillation. It is also known for its varietal gins, with the makers describing themselves as the only distillery focusing on the unique characteristics of each individual species of juniper. Distillery tours and tastings are offered by appointment only, with the tasting room and bar set against scenic farm views and able to host small groups. Visitors interested in the craft of growing and distilling can arrange a visit through the distillery's contact page to sample the brandies and gins firsthand.

No upcoming events listed.

Oakencroft Farm & Winery

Oakencroft Farm & Winery is a sustainability-focused farm and winery about 10 minutes from downtown Charlottesville, Virginia. Built around regenerative farming, the estate tends its soil and vineyards to restore biodiversity, capture carbon, and preserve farmland, working with some of the oldest vines in Virginia to craft expressive, small-batch estate wines. The Tasting Room offers a serene escape where guests can sample these wines alongside a rotating selection of sustainably produced wines from acclaimed regions worldwide, paired with a seasonal menu of locally sourced cheese and charcuterie boards, light bites, and handmade sweets. Visitors can also join the farm and wine clubs for seasonal allocations of estate wines, grass-finished beef, and other local products, or take part in experiences like monthly farm walks. The property includes flexible event spaces, including the Tasting Room, the Fox Den, and the sustainably built Oakencroft Center, making it a venue for weddings, retreats, meetings, and private gatherings in harmony with nature.

Outdoor SeatingB&B

No upcoming events listed.

Potter's Craft Cider

Potter's Craft Cider is a Virginia cidery whose tasting room sits just minutes south of Charlottesville. The cider is made with local Virginia apples using traditional production methods, resulting in a crisp, tart, and refreshing pour with a pronounced fruit aroma, and it is both zero sugar and zero gluten. The tasting room features 10 ciders on draft, giving visitors plenty to sample and compare. Every weekend the space comes alive with live music and local food trucks, making it a lively spot to gather with friends. Guests must be 21 or older to visit.

DogsOutdoor SeatingWeddings

No upcoming events listed.

Roslyn Farm & Vineyard

Roslyn Farm & Vineyard is an agritourism farm estate, vineyard, and winery set in the rolling hills of Central Virginia, just outside Charlottesville near the University of Virginia. Originally built in 1938 as a European-style manor house, the property evokes the French countryside while radiating Southern charm through its architecture, landscape design, and historic gardens. After being acquired in 2015, it was renamed and revitalized into a vibrant farm estate that now blends a vineyard and winery with an equestrian center, farm lodging, and a wedding and event venue. Open to the public, the farm hosts wine tastings and live music on Sundays, Mondays, and Tuesdays, with private tastings available by request. Family-friendly and welcoming to both locals and travelers, Roslyn Farm offers a one-of-a-kind rural retreat in the heart of Virginia wine country.

B&BFamily FriendlyWeddings

No upcoming events listed.

Three Notch'd Craft Kitchen & Brewery

Three Notch'd Craft Kitchen & Brewery is part of the Three Notch'd Brewing Co. family, the Charlottesville-born brewery founded in 2013 by three friends who believed great beer should be fresh, flavorful, and shared. The name comes from the historic Three Notch'd Road that once connected communities across Virginia, and the brewery became known for award-winning beer, creative food, and welcoming gathering spaces. At the Craft Kitchen & Brewery, rotating taps pour fan favorites, seasonal releases, and small-batch experiments, from crisp lagers to bold IPAs, alongside chef-driven comfort food and canned cocktails. Many locations brew on site just steps from where the beer is poured, and select spots also feature Three Notch'd Distilling Co. spirits used in the cocktail program. It is a relaxed, family-friendly spot to grab a pint, share a meal, catch a game, or celebrate with good company.

Family Friendly

No upcoming events listed.

Trump Winery

Step into the Grand Hall Tasting Room and explore a world of award-winning wines in the heart of Virginia's wine country. Enjoy curated tastings, seasonal menu offerings, and an inviting atmosphere where luxury meets relaxation. Whether you're a seasoned connoisseur or a casual taster, every visit is an unforgettable experience of craftsmanship and elegance.

DogsFamily FriendlyOutdoor Seating

• Trump Grand TastingsSat, Jul 18, 2026, 12 PM – 1 PM
• Trump Grand TastingsSat, Jul 25, 2026, 12 PM – 1 PM
• Mimosas & MasterpiecesFri, Jul 31, 2026, 10 AM – 12:30 PM

+ 1 more upcoming event →

Chiswell Farm & Winery

Chiswell Farm & Winery is part of the Chiles Family Orchards, set on a historic Jeffersonian estate in the Virginia countryside in Greenwood, near Crozet on the Monticello Wine Trail. The winery invites guests ages 21 and over to enjoy locally crafted wines, panoramic countryside views, and warm hospitality. Its wines have earned strong recognition, including six awards in the 2026 Virginia Governor's Cup with gold medals for the 2023 Meritage and 2023 Merlot and silver medals for several other vintages. Visitors can build their own tasting flight or choose from recommended flights, including a Governor's Flight of recent award winners, and sip seasonal specialty drinks such as a strawberry citrus spritzer. Open most days of the week, Chiswell also offers the Crown Club membership for those who want to share in the Virginia wine country experience throughout the year.

Outdoor SeatingWeddings

• Virginia Sunflower FestThu, Jul 16 – Sun, Aug 2, 2026
• Music Trivia Night with Rachael Karpo (July)Thu, Jul 16, 2026, 5 PM – 8 PM
• Chiswell Book Club July MeetingSun, Jul 26, 2026, 1 PM – 3 PM

+ 15 more upcoming events →

Fallen Tree Vineyard

Fallen Tree Vineyard is a small-batch farm winery set in the foothills of Crozet, Virginia, within the Monticello AVA. The wines are grown and crafted on site, shaped by the region's hills, weather, and soil, and the portfolio includes Sparkling Rosé, Blanc de Blanc, Chardonnay, Petit Manseng, Viognier, Cabernet Franc, Petit Verdot, and red blends like the Ferenz and Meritage. Visitors can enjoy guided tastings with one-ounce pours led by a wine expert or build a signature flight of four wines with generous two-ounce pours. The on-site kitchen serves wine-friendly small plates featuring local Virginia ingredients, from country ham and artisan cheeses to charcuterie and pizzas, with non-alcoholic options available as well. With sweeping vineyard and mountain views, cozy indoor seating, and outdoor space, Fallen Tree also hosts live music every Saturday and welcomes private events such as weddings and celebrations.

WeddingsOutdoor SeatingFamily Friendly

No upcoming events listed.

Glass House

Glass House Winery is a boutique winery and brewery in central Virginia, founded in 2006 and part of the Monticello Wine Trail near Charlottesville. Known for its tropical flair, the estate grows and cultivates its own grapes to make artisan wines that reflect the terroir of the region, and it has since added the Glass House Brewery to its offerings. Beyond wine and beer, the venue is known for its handcrafted chocolates and its distinctive glass conservatory setting. Weekends often feature live music with local artists, along with special events such as chef-led brunches. Visitors can also extend their stay at the on-site bed and breakfast, making Glass House a destination for a full weekend getaway in Virginia wine country.

DogsOutdoor SeatingOutside Food

• Ken Farmer & The Authenticators with Brick City Kitchen Food TruckFri, Jul 17, 2026, 6 PM – 8:30 PM
• Bunch O' MugsSat, Jul 18, 2026, 5 PM – 8 PM
• Midnight Buzz DuoSun, Jul 19, 2026, 2 PM – 5 PM

+ 4 more upcoming events →

Grace Estate Winery

Grace Estate Winery is a family-run winery in Crozet, Virginia, about a 15-minute drive from Charlottesville in the Monticello AVA, producing traditionally made, premium artisanal wines from estate-grown old vines in its mountain vineyard. The winery has earned strong critical recognition, including multiple Gold Medals at the Virginia Governor's Cup and high scores from James Suckling for bottlings such as its Slope of Grace Cabernet Franc, Odo Red, Colonel Richard Tannat, and Gange-Rolv Chardonnay. Visitors can reserve tastings and tours, sample current releases in a modern tasting room, and relax on an outdoor patio with a bar, with live music offered every weekend during the season. The historic Grace Estate mansion on the property hosts private events and weddings, and guests can join the Silo Society wine club or shop wines online. With its scenic setting and award-winning lineup, Grace Estate offers a well-rounded Virginia wine country experience.

Weddings

No upcoming events listed.

King Family Vineyards

King Family Vineyards is a family-owned and operated winery set in the foothills of the Blue Ridge Mountains in Crozet, Virginia, about 15 minutes from Charlottesville. Farming since 1998, the estate produces premium wines that express the terroir of the Monticello AVA under winemaker Matthieu Finot, including sparkling, white, rosé, and red wines, the Meritage program, and a Small Batch Series. Visitors can taste in the daily-open tasting room, relax on the patio with mountain views, or join Founder's Farm and Vineyard Tours led by co-founder Ellen King aboard a golf cart. A signature draw is Roseland Polo, with Sunday polo matches that invite guests to tailgate and watch from the lawn. The property is also a popular destination for weddings and private events, and offers a wine club for members.

Weddings

• Wine Wednesday (July 15)Wed, Jul 15, 2026, 4:30 PM – 8:30 PM
• USPA National Sherman Memorial PoloFri, Jul 17, 2026, 4 PM – 9 PM
• Author Night: Jo PiazzaFri, Jul 17, 2026, 7 PM – 9 PM

Pollak Vineyards

Pollak Vineyards is a small family-owned estate winery in Greenwood, Virginia, set on a farm west of Charlottesville and Crozet against the backdrop of the Blue Ridge Mountains. Founded by the Pollak family in 2003, the winery was built around a simple vision of making estate-grown wines that reflect the beauty and character of the region, with vineyards planted in French vinifera and farmed with a long-term commitment to quality, balance, and a sense of place. The award-winning wines are grown and made on site, and the tasting room and patio offer picturesque views of the vines, the pond, and the nearby mountains. Visitors can enjoy guided wine tastings on weekdays, or stop in any day for glasses, flights, and bottles paired with a la carte cheeses, charcuterie, and fresh bread. The winery is open Wednesday through Monday, and guests can also join the Smuggler Society wine club for preferred pricing and member-only experiences.

Family FriendlyOutdoor Seating

• America 250 Series: An Evening with Lucie MortonFri, Jul 17, 2026, 6 PM – 8 PM
• America 250 Series: An Evening with Fred RenoFri, Jul 24, 2026, 6 PM – 8 PM
• Final Fridays Concert: Blake Hunter & the GatherersFri, Jul 31, 2026, 5:30 PM – 8:30 PM

Pro Re Nata Brewpub

Pro Re Nata Brewery is a brewery and music hall in Crozet, Virginia, just west of Charlottesville. Open since 2015, it brews craft beers and pairs them with food, drinks, live music, and a welcoming community atmosphere. The venue is laid out across three distinct zones: the Main Tap Room, home to the kitchen, seating, and a stage with live music most nights; the Original Brewery, featuring a copper bar, guest flags hung from the ceiling, and twelve TVs with full sports packages; and the Farmacy, an open-air event space built around a shipping container with its own outdoor bar, stage, and kids' play area. Outdoor seating surrounds all three areas, with fire pits and scenic views for relaxing. The brewery is open Thursday through Sunday and serves as a popular gathering spot in Central Virginia for any occasion.

Family FriendlyDogsOutdoor Seating

• Supernova — A Tribute to OasisThu, Jul 23, 2026, 6:30 PM
• Shotguns N Roses: A Powerful Blast of GNRFri, Jul 31, 2026, 7 PM
• Isaac Hadden w/ Dara James & The Soul Disciples feat. John Daniel Ray & Jeff SipeFri, Aug 14, 2026, 7 PM

+ 5 more upcoming events →

Septenary Winery

Septenary Winery is a Virginia winery set on historic Seven Oaks Farm, a property whose storied tradition dates back to the 1700s when it was home to one of Virginia's first taverns. The winery is open to the public Thursday through Sunday from 11:00am to 5:30pm, offering wine by the glass or bottle as well as tasting flights. Guests can settle into limited indoor seating or ample outdoor space, with reservations required for groups of six or more and private tastings available by appointment. Septenary is an adults-only facility, welcoming guests 21 and over. Beyond tastings, the winery offers a quarterly wine club and hosts private events and celebrations such as birthdays, anniversaries, rehearsal dinners, and receptions in customizable indoor and outdoor spaces.

Outdoor SeatingPicnic

No upcoming events listed.

Starr Hill Brewery - Crozet

Starr Hill Brewery is an independent, regional craft brewery that was born in a Charlottesville music hall in 1999 and has been brewing beer in Virginia ever since. Its Crozet location serves as the brewery's production home and taproom, one of six Starr Hill spots that also include Charlottesville, Lynchburg, Roanoke, Richmond, and Tysons. Visitors to the Crozet taproom can enjoy a rotating lineup of the brewery's craft beers, from year-round favorites to seasonal and limited releases, in a relaxed setting that nods to the brewery's roots in live music. The taproom welcomes guests for casual visits and can also host private events and gatherings. Beyond the beer, Starr Hill offers branded apparel and merchandise, gift cards, and regular news about new brews and label designs.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Stinson Vineyards

Stinson Vineyards is a family- and winemaker-owned estate winery in Virginia's Blue Ridge Mountains, located near Charlottesville within the Monticello AVA. The winery specializes in small-batch, garagiste-style wines made in small lots, a tradition carried on by the father-daughter team of Scott Stinson and Rachel Stinson Vrooman, who were joined by Rachel's husband Nathan Vrooman in 2015. Visitors can taste the estate's small-production wines in the tasting room while taking in the surrounding mountain views. Guests looking to extend their stay can book a room at The Inn at Stinson Vineyards, the winery's on-site bed and breakfast. The combination of fine wines, scenic setting, and warm hospitality has made it a popular stop in the region's wine country.

B&B

• Tailgate Thursday: Susie + The Pistols & OCSF OystersThu, Jul 16, 2026, 6 PM – 9 PM
• Tailgate Thursday: Moonglow & Crozet SeafoodThu, Jul 23, 2026, 6 PM – 9 PM
• Tailgate Thursday: Scuffletown & OCSF OystersThu, Jul 30, 2026, 6 PM – 9 PM

12 Ridges Vineyard

12 Ridges Vineyard is a high-elevation winery set along the Blue Ridge Parkway at Mile Post 25 in Vesuvius, Virginia, sitting at roughly 3,300 feet, which makes it one of the highest vineyards in the eastern United States. The cool mountaintop climate, with its wide diurnal temperature swings, strong wind, and intense sunlight, slows ripening and preserves natural acidity, producing wines of structure and precision that the vineyard likens in spirit to cool-climate European regions such as Burgundy, Champagne, Alsace, and Germany. About ten acres are planted to Chardonnay, Riesling, Pinot Noir, and Pinot Gris, varieties chosen specifically for high-elevation conditions, and the winemaking emphasizes restraint to let the site speak. Visitors can taste these wines in a quiet, understated tasting room with uninterrupted long-range views across the Blue Ridge Mountains. For those who wish to linger, a small collection of private homes on the property, including a Vineyard House and a Mountain House, lets guests extend their stay amid the elevation and sweeping mountain scenery.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Afton Mountain Vineyards

Afton Mountain Vineyards is one of Virginia's pioneering wineries, with vines first planted in 1978 on the eastern slope of its namesake Afton Mountain in the heart of the Blue Ridge. Set at nearly 1,000 feet of elevation amid 24 acres of vines spanning 11 grape varieties, the estate pairs sweeping mountain and vineyard views with award-quality wines crafted by French-born winemaker Damien Blanchon. Visitors can enjoy tastings and tours in the Tasting House, relax at the on-site pavilion, stay overnight in one of the vineyard's charming cottages, or host weddings and private events against a stunning Shenandoah Valley backdrop — making it a memorable destination for wine lovers and travelers alike.

WeddingsB&B

• Meetin on the Mountain: British Car ShowSat, Jul 18, 2026, 12:30 PM – 3 PM
• Live Music: Hartwell Jazz QuartetSat, Jul 18, 2026, 4 PM – 7 PM
• Live Music: Betsy in the VerseSat, Jul 25, 2026, 4 PM – 7 PM

Blue Mountain

Blue Mountain Barrel House is a brewery and restaurant in Arrington, Virginia, serving as the sister operation to the original Blue Mountain Brewery in Afton. Billed as Virginia's first rural brewery, it has independently brewed and packaged its beers on site since 2012, and also produces all the beer for South Street Brewery. Visitors can sample a wide lineup spanning a core series, seasonal offerings, and the barrel-aged Barrel House series, with flagship beers like the Full Nelson Virginia Pale Ale, Kolsch 151, and the barrel-aged Dark Hollow Imperial Stout. The on-site Smokin' Barrel Restaurant rounds out the experience with sandwiches, pizzas, and a Sunday brunch. Guests can also take advantage of daily specials, growler fills, and live music during Friday Cheers, making it a relaxed destination for food, beer, and gatherings in Nelson County.

Outdoor Seating

• Steal the GlassWed, Jul 15, 2026, 11 AM – 8 PM
• Friday Cheers with Jason "Tater" TomlinFri, Jul 17, 2026, 5:30 PM – 8 PM
• Friday Cheers with Alex Arbaugh TrioFri, Jul 24, 2026, 5:30 PM – 8 PM

+ 1 more upcoming event →

Blue Toad Hard Cider

Blue Toad Hard Cider is a craft cidery and taproom nestled in the Blue Ridge Mountains of Nelson County, Virginia, producing award-winning dry hard ciders made exclusively from locally grown apples sourced from Western New York and Nelson County. The cidery takes a farm-to-can approach with all-natural, handcrafted ciders, including its decorated Paddy Green, which has earned a Gold medal at the Great Lakes International Cidery and Perry Competition and a Silver at the Virginia Governor's Cup. Visitors to the cider farm can enjoy pints, flights, and growler fills in the taproom, with happy hour specials, Sunday deals, and Heartland Wines also available for tasting and bottle sales. The property is a lively community hub, hosting live music, food trucks, festivals, and signature events like the Rockfish River Rodeo. Guests can join the Blue Toad Cider Club for bi-monthly shipments, and the on-site Cider Hall serves as an outdoor venue for weddings, corporate retreats, and other gatherings with scenic mountain views.

Family FriendlyOutdoor SeatingDogs

No upcoming events listed.

Bold Rock

Bold Rock Nellysford is a craft cidery, taproom, and restaurant in Nellysford, Virginia, set along the scenic Nelson 151 craft beverage trail in the Blue Ridge Mountains. The flagship Bold Rock Cider Barn, opened in August 2014, is a rustic timber-framed barn known as the "Chapel of Apple" that serves as the company's headquarters and primary cider production facility, with stunning views of the Rockfish River and surrounding mountains. Visitors can enjoy Bold Rock's gluten-free hard ciders, ranging from dry and crisp to sweet and fruity and made from locally sourced apples, alongside craft beers from sister brands and a full Bold Kitchen menu of lunch and dinner fare designed to pair with cider. The property also includes the Bold Rock Distillery at the Barrel Barn, a destination for craft cocktails, canned cocktails, seltzers, ciders, and wines. With a pint, a tasting flight, weekly food and drink specials, taproom events, a rewards club, and space to host private events, Bold Rock Nellysford offers a family-friendly spot to relax along Route 151.

DogsOutdoor Seating

• US History Trivia Month - Civil WarFri, Jul 17, 2026, 6 PM – 8 PM
• Sip & Savor: A Cider DinnerTue, Jul 21, 2026, 6 PM – 8 PM
• Magic The Gathering MeetupThu, Jul 23, 2026, 6 PM – 9 PM

+ 2 more upcoming events →

Bryant’s Dry Cider

Bryant's Dry Cider is a Virginia cidery and brewery whose ciders are crafted from apples grown on its historic estate farm in Nelson County, near Roseland in the rural Blue Ridge mountains. The company traces its apple-growing roots back more than a century, and today produces a range of gluten-free craft ciders that span from extra dry to moderately sweet, along with estate-produced beers. Visitors can taste at the Bryant's Farm tasting room, set in an 1800s building that hosts weekly events for the whole family, and there is also a second tasting location, the Lab, in Richmond. The farm setting offers history and nature alongside the drinks, and the venue is available for weddings and other gatherings. Guests can join the Cider Club, order online, or stop in to sample the lineup.

DogsFamily FriendlyWeddings

No upcoming events listed.

Cardinal Point Winery

Cardinal Point Winery is a family-operated farm winery in Nelson County, Virginia, ideally situated within view of the Rockfish Gap, the Blue Ridge Parkway, and Skyline Drive. Established in 1985, the winery produces limited-production, handcrafted wines that showcase the unique style and terroir of the Monticello American Viticultural Area in the heart of Virginia wine country. Its portfolio spans a range of grape varieties grown and produced on the estate, including offerings such as Rockfish Red, Hopped Chardonnay, and Clay Hill Cabernet Franc. The tasting room welcomes guests daily between 11 a.m. and 5:30 p.m., offering tastings along with glass and bottle sales and both indoor and outdoor seating areas. Visitors can also join the Cardinal Point Cooperative wine club for access to award-winning wines, special pricing, and discounted event reservations.

Outdoor Seating

No upcoming events listed.

Devils Backbone

Devils Backbone Brewing Company is a Virginia craft brewery known for its award-winning beers and its setting in the Blue Ridge Mountains. The brewery operates two pub locations, the Basecamp Brewpub & Meadows and the Outpost, where visitors can enjoy a wide range of house brews along with the company's SMASH ready-to-drink canned cocktails. Beyond the taproom, Basecamp offers an array of experiences including a regular concert series, festivals, and other events held on its scenic grounds. Guests can extend their visit by camping at Basecamp or staying in its on-site lodging, and the property is also available for private events. With food, drink, music, and mountain getaways all in one place, Devils Backbone aims to feel like home.

Outdoor Seating

• Fall Lumberjack Classic WeekendFri, Sep 18 – Sat, Sep 19, 2026

Flying Fox Vineyard

Flying Fox Vineyard is a small, family-run Virginia winery that has been producing premium wines since 2006 with a philosophy of uninhibited winemaking. Run by a team with collectively half a century of experience in the Virginia wine industry, the operation deliberately keeps its focus narrow, prioritizing wine itself over events, wide wholesale distribution, or food service. The winery farms two vineyard sites to take advantage of climatic variability: Flying Fox Vineyard in the warmer Monticello AVA, where its red varieties grow, and the cooler, higher Ridge Run Vineyard in the Shenandoah AVA, home to its whites. Its core Flying Fox Series offers eight premium varietal wines, such as viognier and petit verdot, that aim to express the fruit and place authentically, while the experimental Sly Fox Series and an award-winning seasonal vermouth let the team push beyond convention. The result is a limited-production, varietally focused portfolio meant to honor Virginia's emerging wine industry.

DogsOutdoor SeatingOutside Food

No upcoming events listed.

Hazy Mountain

Hazy Mountain is a family-owned winery in the Blue Ridge Mountains of Virginia that produces wine from its own estate vineyards. With 86 acres under vine across two sites in Afton and Swoope, the winery proudly represents both the Monticello and Shenandoah Valley AVAs, aiming to let the vineyards speak for themselves and tell the story of what their distinctive soils have to offer. Guests can personalize their visit with guided tastings, offered seven days a week in the tasting room, with private guided tastings available upon request. The winery also offers a tiered wine club with four membership levels, plus tasting room and online shop discounts, for those who want to enjoy more Hazy Mountain at home. Beyond tastings, Hazy Mountain hosts weddings and private events in its dedicated vineyard event spaces and maintains a calendar of ongoing happenings throughout the year.

Family FriendlyWeddings

• Nelson SPCA Donation DriveThu, Jul 2 – Fri, Jul 31, 2026
• Paint + Sip "Tropical Paradise"Fri, Jul 31, 2026, 6 PM – 8 PM
• The Beekeeper's Table Secret SupperFri, Aug 14, 2026, 6 PM – 9 PM

Hill Top Berry Farm & Winery

Hill Top Berry Farm & Winery is a family-run winery and meadery in Nellysford, Virginia, in the scenic Rockfish River Valley along the Route 151 corridor in the Blue Ridge. It first opened in 1993 as a pick-your-own berry farm and in 1998 became the fifty-first winery to open in Virginia. The winery specializes in "true to the fruit" wines made from fruits such as blueberries, blackberries, plums, apples, peaches, and elderberries, alongside historically accurate honey meads, with all 32 varieties handcrafted in small batches and bottled on the farm. Visitors can sample these fruit wines and ancient-style honey meads while learning the history behind each one, and enjoy tasting flights and charcuterie out on the patio. Set amid orchards and farmland with mountain views, Hill Top is part of a region known for wineries, breweries, cideries, hiking, and outdoor recreation, and it offers a discount to veterans, military members, and law enforcement.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Mountain & Vine

Mountain & Vine Vineyards and Winery is an estate winery in Faber, Virginia, in the Charlottesville area. Its European-styled terraced vineyards create distinctive grape-growing conditions, and the team of viticulturists and winemakers works that challenging terrain to produce a lineup of award-winning wines. Visitors can sample the wines from a rotating tasting menu in the tasting room, which also offers charcuterie-style grab-and-go snacks and non-alcoholic beverages. Guests can shop the wines on site or online to take their favorites home. With panoramic mountain vistas and relaxing accommodations, Mountain & Vine offers a scenic setting for an afternoon of tasting or a longer stay in Virginia wine country.

DogsFamily FriendlyWeddings

No upcoming events listed.

Ragged Branch

Ragged Branch Distillery is a Virginia craft distillery that got its start among friends on a Charlottesville farm and is now located at 1054 Old White Bridge Road in Waynesboro. Its mission is to honor Virginia's bourbon-making heritage through authentic, sustainable production, building its whiskeys on a foundation of true craftsmanship. The distillery's lineup includes a Signature Bourbon, a Wheated Bourbon, the higher-proof Cowboy Cut wheated bourbon, and a Rye Whiskey, all proudly crafted and bottled in Virginia. Visitors are welcome to come out to the distillery to learn about its farm-rooted approach and sample the spirits firsthand. With its emphasis on local grain and traditional methods, Ragged Branch offers a genuine taste of Virginia's growing whiskey scene.

No upcoming events listed.

Silverback Distillery

Silverback Distillery is an internationally awarded craft distillery led by Master Distiller Christine Riggleman, founded in 2014. The independent, small-batch operation produces distinct, flavorful spirits from a unique mix of local grains, mountain water, and American craftsmanship, including the citrus-forward Strange Monkey Gin, honey-infused Blackback Rye Whiskey, Blackback Bourbon, and the acclaimed Christine Riggleman Reserve, the first bourbon branded under a woman's name. Silverback operates production facilities and tasting rooms in both the Pocono region of Pennsylvania and the Blue Ridge Mountains of Virginia, giving visitors two locations to explore. Guests can enjoy a range of tasting experiences, from cocktail flights and barrel-smoked cocktails to whiskey served neat. The distillery takes its name from a family nickname and prides itself on creating high-quality, approachable spirits meant to be enjoyed by everyone.

DogsOutdoor Seating

No upcoming events listed.

Valley Road Vineyards

Valley Road Vineyards is a Virginia farm winery located at the gateway to the Nelson 151 trail at 9264 Critzers Shop Road in Afton, within the historic Monticello Viticultural Area. Founded in 2016, the winery focuses on outstanding estate wines and farms roughly a dozen-plus acres under vine; it is a member of the Monticello Wine Trail and a winner of the 2026 Virginia Governor's Cup. Visitors can sample wines in the farm-chic tasting room or relax outdoors on the Patio, the Pavilion overlooking the Blue Ridge Mountains, or in the shade of the Grove. The winery is open seven days a week, offers a wine club and regular events, and is a popular setting for weddings and private celebrations. Its scenic location makes it a natural first stop for those exploring the Nelson 151 corridor.

Outdoor SeatingWeddingsFamily Friendly

• Late Friday + Live Music with Gina Sobel and Matt DraperFri, Jul 24, 2026, 5 PM – 7 PM
• Live Music with Shane ClickSat, Jul 25, 2026, 2 PM – 5 PM
• Late Friday + Live Music with Travis ElliottFri, Aug 7, 2026, 5 PM – 7 PM

+ 6 more upcoming events →

Veritas Vineyard and Winery

Veritas Vineyard and Winery is a top-rated, family-owned winery located at 151 Veritas Lane in Afton, Virginia, about 20 minutes west of Charlottesville in scenic Nelson County. A proud member of the Nelson 151 Trail, the estate produces award-winning wines and offers a tasting room open daily from 11:00 a.m. to 5:00 p.m. Visitors can enjoy wine tastings, settle in at one of the winery's tables to take in the vineyard views, and explore the seasonal menu and wine list. The property is also a popular destination for weddings and hosts a calendar of events throughout the year, including its Supper Series, Starry Nights, and Veritas Illuminated. Guests can join the wine club for quarterly hand-selected releases and member benefits, and the on-site Farmhouse offers an additional dining and lodging experience.

DogsPicnic

• Veritas Supper Series — Southern RootsFri, Jul 24, 2026, 6:30 PM
• Veritas Supper Series — Mid-Atlantic Blue CrabFri, Aug 21, 2026, 6:30 PM
• Starry Nights @ VeritasSat, Aug 22, 2026, 5:30 PM – 11 PM

+ 6 more upcoming events →

Virginia Distillery Co.

Virginia Distillery Co. is an American Single Malt whisky distillery set in the heart of Virginia's Blue Ridge Mountains, in central Virginia. The distillery describes itself as the most awarded single malt whisky distillery in America, earning recognition from top industry experts and prestigious competitions for its grain-to-glass craft. At its Visitors Center, guests can book guided tours and tastings to explore the distillery's process, history, and award-winning whisky firsthand. The distillery also hosts a calendar of special events and experiences, and shares whisky cocktail recipes ranging from classic Old Fashioneds to original creations. Its flagship offerings include the Courage & Conviction brand of American Single Malt, with educational resources available through the American Single Malt Academy.

Family Friendly

No upcoming events listed.

WildManDan Brewery

WildManDan Brewery is an artisan production brewery in Afton, Virginia, and a member of the Nelson 151 Craft Beverage Trail, where it has been recognized among the trail's best. The brewery is a 21-and-over establishment open to the public, specializing in small-batch beer and welcoming visitors Wednesday through Sunday, with hours that include weekday afternoons and evenings. Beyond the taproom, the property offers a Mountain Farmhouse that sleeps 12, available for group bookings with farm-to-table catering for guests staying the weekend. Regular happenings give the brewery a community feel, including Run, Walk, Crawl on Wednesdays, Locals Vinyl nights with five-dollar pints on Thursdays, and a Saturday grilled cheese and beer pairing with limited seating. The brewery also hosts seasonal events such as the Nelson 151 Honey Daze celebration and shows all Green Bay Packers games, making it a relaxed spot for craft beer and casual gatherings in the Virginia mountains.

B&BOutside FoodOutdoor Seating

No upcoming events listed.

Castle Hill Cider

Castle Hill Cider is an artisanal cidery and premier event venue set on 650 acres of picturesque countryside in Keswick, just outside Charlottesville, Virginia. The estate is best known as a stunning wedding and event destination, offering a curated collection of spaces that range from intimate gatherings to large celebrations. Couples and guests can choose among settings such as the Terrace, Linden Grove, sweeping lawns and mountain views, a reception barn, a loft, and private suites for getting ready. The property pairs its scenic Virginia landscape with the craft of cider making, creating a backdrop for memorable weddings and special occasions. Castle Hill Cider is currently booking events into 2026 and 2027, with limited dates still available in 2025.

Outdoor SeatingWeddingsB&B

No upcoming events listed.

Cunningham Creek Winery

Cunningham Creek Winery & Brewery is a family-owned and operated small-lot winery and brewery on the Monticello Wine Trail in Fluvanna County, Virginia, about 20 minutes from Jefferson's Monticello, 30 minutes from Charlottesville, and 10 minutes from Lake Monticello. The boutique winery produces only about 2,000 cases a year of finely crafted French varietals and Bordeaux-style blends, all made on site by winemaker Bruce, and has earned numerous honors including multiple Virginia Governor's Cup and Monticello Cup medals. It is also the first brewery in its community, pouring a selection of craft beers on tap alongside the wines. Visitors can taste in the air-conditioned tasting room or relax in the newly expanded outdoor seating, and the winery is family, dog, and picnic friendly, with a dog park where pups can run off-leash. Regular events include live music on Saturday nights and team trivia on the third Thursday of each month.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Keswick Vineyards

Keswick Vineyards is a family-owned and operated winery near Charlottesville, Virginia, in the Monticello wine region. Founded in 2000, its first vintage earned the honor of Best White Wine in America at the Atlanta International Wine Summit in 2002, and the winery has since gone on to win two Virginia Governor's Cups along with numerous Gold, Double Gold, and Platinum awards. The family-friendly tasting room offers an elevated food menu through its in-house kitchen, Barrel & Board, plus a miniature golf course, a dog park, and live music. Visitors can taste the winery's wines, join the wine club, and attend regular events such as the Wine Down Wednesday live music series. The estate is also a popular setting for weddings and is a proud partner of Virginia Tourism.

DogsFamily FriendlyOutdoor Seating

• Wine Down Wednesday – The UnsuitablesWed, Jul 15, 2026, 5:30 PM – 8:30 PM
• Live Music – Big Gavel Country BandSat, Jul 18, 2026, 1 PM – 4 PM
• Wine Down Wednesday – South Canal Street BandWed, Jul 22, 2026, 5:30 PM – 8:30 PM

+ 4 more upcoming events →

Merrie Mill Farm & Vineyard

Merrie Mill Farm & Vineyard is a family-owned winery and tasting room destination in Keswick, Virginia, near Charlottesville. Founded by Guy and Elizabeth Pelly, it reimagines the tasting room experience by pairing warm, approachable hospitality with a playful, maximalist setting known for its bold interior design and unexpected artwork. The tasting room features two copper bars in a lofted interior, with multiple terraces and lawns overlooking the vineyards and views up the South West Mountains. Guests can make reservations for wine tastings and lovingly prepared food, sample estate-grown wines such as the rose, Viognier, and white blend, and join the winery's club. Merrie Mill also hosts special events and live music, including Friday Sundowners and Sunday blues and jazz, and offers overnight stays next door at the two-bedroom Clementine Cottage with views over the vineyard.

Outdoor SeatingWeddingsB&B

• Friday Sundowner's Music Series featuring Blane Perry and Bob LedbetterFri, Jul 17, 2026, 5:30 PM – 8:30 PM
• Sunday Jazz and Blues featuring Elliot CurrieSun, Jul 19, 2026, 1 PM – 4 PM
• Friday Sundowner's Music Series featuring Jacob Paul AllenFri, Jul 24, 2026, 5:30 PM – 8:30 PM

+ 29 more upcoming events →

Southwest Mountains Vineyards

Southwest Mountains Vineyards is an estate winery in Keswick, Virginia, just outside Charlottesville in the rolling hills of the Monticello AVA. At the heart of the property is the Tasting Barn, a fully restored 1903 structure that now houses the tasting room and pairs historic character with an understated, modern approach to hospitality. The estate vineyards are cultivated in the area's distinctive soils and climate, and the wines are made with a minimalist approach in the cellar to reflect a sense of place. Visitors can choose from guided tasting flights or relaxed by-the-glass visits, with both intimate indoor seating and open-air tables overlooking the vineyard, and reservations are recommended though walk-ins are welcome. Beyond tastings, SMV offers The Glade, a bookable hiking, wine, and lunch experience along an estate trail, as well as private events, seasonal festivals and winemaker dinners, and a wine club with seasonal selections and member benefits.

Outdoor SeatingPicnicOutside Food

• Guest Star Hike with BoelaSat, Jul 25, 2026, 12 PM – 2 PM
• Blooms 4 Good Floral WorkshopSun, Jul 26, 2026, 1 PM – 5 PM
• Summer Culinary Series: Pours & Pasta (Thursday)Thu, Jul 30, 2026, 6:30 PM – 9 PM

+ 1 more upcoming event →

Bald Top Brewing Co.

Bald Top Brewing Co. is billed as Virginia's first historic farm brewery, located at 1830 Thrift Road in Madison, Virginia. The taproom pours 20 taps of house-brewed Bald Top beer alongside wine and cider, and its made-from-scratch Scratch Kitchen serves pizza, BBQ, and other fare. Set on a farm with sweeping views from the lawn to the surrounding mountains, the brewery offers a relaxed setting for food and drink. Visitors can enjoy live music, and the property includes event spaces available for private bookings. An interactive virtual tour lets guests preview the taproom, kitchen, and grounds before stopping by.

DogsOutdoor Seating

No upcoming events listed.

Barboursville Vineyards

Barboursville Vineyards is a historic estate winery in Barboursville, Virginia, in the Monticello wine region, known as one of the state's most celebrated producers. Its flagship wine is Octagon, a Bordeaux-style red blend that has earned recognition including a Gold medal at the Virginia Governor's Cup and repeated appearances on national best-of lists, and the estate draws on Italian winemaking heritage with bottlings such as its long-running Nebbiolo. Visitors can take part in tastings and tours, dine at the on-site Palladio Restaurant, and stay overnight at the estate's Inn and cottages. The property also hosts private parties and weddings, and grounds include the historic ruins of the Barboursville mansion. With its focus on sustainability and acclaimed wines, the estate offers a full destination experience for visitors to central Virginia wine country.

WeddingsB&B

No upcoming events listed.

Chestnut Oak Vineyard

Chestnut Oak Vineyard is a winery on the Monticello Wine Trail, located in Barboursville, Virginia within the Monticello AVA and about 20 minutes north of Charlottesville. Visitors can enjoy flight tastings, wine by the glass, or bottles to share in the tasting room or outdoors with views of the surrounding mountains, with curbside pickup also available. The vineyard produces a range of wines from light to robust, including Cabernet Sauvignon, Merlot, Petit Verdot, Nebbiolo, Viognier, Chardonnay, Petit Manseng, and Tannat, and counts Virginia Governor's Cup medal winners among its bottlings. A free wine club offers members a 20 percent discount along with quarterly releases in March, June, September, and December that can be shipped or picked up. The tasting room is open Friday through Monday, making it a relaxed stop among the many wineries near Charlottesville.

Outdoor SeatingDogs

No upcoming events listed.

Ducard

DuCard Vineyards is an authentic farm winery in Etlan, Madison County, Virginia, set against the eastern slope of Shenandoah National Park near Old Rag Mountain. Its wines are handmade on site using traditional methods from estate grapes grown at three local Madison County vineyard sites, an approach that has earned the winery gold medals and 90-plus point ratings along with recognition as a top-rated Central Virginia winery and a leader in environmental sustainability. Visitors can settle in for full-service wine flights of reds and whites served in crystal glassware at their table, or enjoy current-release and library wines by the bottle. The setting offers comfortable seating at mountain-view tables on the back lawn, a stream-side deck, a pavilion, and an air-conditioned event room, all surrounded by scenic Blue Ridge views. DuCard is family-friendly, dog-friendly, and picnic-friendly, with live music on weekends and a calendar of special events, plus optional reservations and space for private gatherings.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Early Mountain Vineyards

Early Mountain Vineyards is a Virginia winery in Madison, in the heart of the state's wine country, founded in 2012 by Jean and Steve Case with the belief that Virginia can produce wines that stand alongside the finest in the world. Guided by winemaker Maya Hood White and her team, the winery emphasizes a strong commitment to the vineyard and an expression of place, crafting high-quality wines that have helped lead Virginia's rise as a respected wine region; its 2023 Petit Manseng was recently named "a benchmark for the state" by Decanter. Visitors come to the award-winning tasting room to enjoy curated wine flights, a tasting bar, and the in-depth Elevation tasting featuring library and exclusive wines, all led by knowledgeable educators. The experience is paired with a renowned culinary program, where Chef Tim Moore and his team turn seasonal produce from local farms into dishes designed to complement the wines. Beyond tastings, Early Mountain offers a wine club, on-site stays, special events and wine dinners, and serves as a premier venue for weddings and private gatherings amid its scenic mountain surroundings.

Outdoor SeatingWeddings

• Wine & Cheese Pairing ExperienceSun, Aug 2, 2026, 2 PM

Horton Vineyards

Horton Vineyards is a pioneering, family-run Virginia winery set in the scenic countryside of Orange County at 6399 Spotswood Trail in Gordonsville. Now a three-generational operation led by remarkable women, founder Sharon Horton still oversees the vineyard she began decades ago, second-generation Shannon Horton bridges vineyard and winery, and winemaker Caitlin Horton crafts the vintages from grapes her grandmother nurtured. The winery is known as one of the East Coast's most unique vineyards, blending tradition with innovation and continually exploring new varietals and techniques, with a signature Viognier among its many award-winning bottlings. The tasting room offers a self-guided experience drawn from a lineup of more than 40 wines spanning whites, reds, rosés, and distinctive fruit and dessert wines, with knowledgeable staff on hand to help guests choose. Horton is open daily year round from 10am to 5pm (closed Thanksgiving and Christmas Day), and visitors can also join its Monthly or Fill the Cellar wine clubs.

Family Friendly

• Bordeaux Library Tasting: Petit Verdot | MalbecSat, Aug 1, 2026, 3:30 PM
• Quests & Cabernet at Horton VineyardsSun, Aug 16, 2026, 4 PM
• Horton on the Go: Stratford Hall Wine & Oyster FestivalSat, Sep 19 – Mon, Sep 21, 2026

+ 6 more upcoming events →

Patch Brewery

Patch Brewing Co. is a craft brewery and neighborhood gathering spot in Gordonsville, Virginia, about 25 minutes northeast of Charlottesville. Housed in a former VFW hall, the brewery sits on roughly 14 acres of green space and pours its own house-brewed beer alongside local cider, local wine, and canned cocktails. Food comes from its own County Line Food Truck, serving smash burgers and light fare every day the taproom is open, with both indoor seating and an outdoor pavilion available. The grounds are built for families and groups, featuring a dog park, kids and adult areas, a baseball field, walking trails, and lawn, board, and arcade games. Live music rounds out the experience, making Patch a relaxed, all-ages destination on the way into town.

DogsFire PitsOutdoor Seating

No upcoming events listed.

The Market at Grelen

The Market at Grelen is a European-style garden shop, café, and nationally recognized garden wedding venue set on a 1,000-acre tree nursery in Somerset, Virginia. The garden center offers seasonal plants, shrubs, trees, garden accessories, and gifts, while the café serves farm-to-table fare, small-batch ice cream, and Virginia beer, cider, and wine with outdoor and greenhouse seating. Beyond shopping and dining, visitors can explore six miles of hiking trails, pick their own fruit, and pose at the Virginia Living LOVE sign amid the display gardens. The property hosts weddings and events for groups of all sizes across spaces including the Market, Boxwood Villa, Spotswood Lodge, and The Depot, several of which offer overnight lodging. Seasonal offerings round out the experience, from Christmas trees, handmade wreaths, and holiday workshops in winter to an on-site landscape nursery supplying plants and landscaping services.

DogsOutdoor SeatingWeddings

No upcoming events listed.

Virginia Foothills Distillery & Co

Virginia Foothills Distillery & Co is a craft distillery located at 5361 Spotswood Trail in Barboursville, in the foothills near Orange, Virginia. Inspired by local ingredients, the distillery produces small-batch spirits including bourbon whiskey, brandy, and rum, reviving a distilling tradition that traces back to the early history of Virginia, often called the birthplace of American distilled spirits. Visitors can stop in to taste and learn about the spirits, with the tasting room open Wednesday through Sunday and closed on Mondays and Tuesdays. The distillery also offers merchandise and online ordering through its store. Set in the scenic central Virginia countryside, it makes for a relaxed stop for those exploring the region's wineries and craft beverage makers.

No upcoming events listed.

Woodbrook Farm Vineyard

Woodbrook Farm Vineyard is a family-owned and operated vineyard and winery located at 11461 Spicers Mill Road in Orange, Virginia, in the rolling countryside of the state's Piedmont. The owners take pride in sharing the rich history of their working farm with guests who stop in to taste and buy their wines. The tasting room is open Thursday through Sunday, with extended Friday and Saturday hours, offering a relaxed, welcoming setting to enjoy a glass or pick up bottles to take home. The vineyard is dog-friendly, welcoming leashed pets both indoors and out, and visitors are encouraged to bring their own food. Wines can also be purchased online and shipped within Virginia, making it easy to enjoy Woodbrook Farm's offerings at home.

DogsOutside Food

• Winner's Circle Wine Club Appreciation PicnicSat, Jul 18, 2026, 2 PM – 5 PM
• Live Music: Cason Spencer + Cousin's Maine Lobster Food TruckSat, Jul 25, 2026, 2 PM – 5 PM

Albemarle Ciderworks

Albemarle Ciderworks is an artisan cidery and orchard in North Garden, Virginia, just south of Charlottesville, operated by the Shelton family alongside their Vintage Virginia Apples nursery. The cidery celebrates cider making as an American tradition, handcrafting small-batch artisan ciders from locally grown heirloom apples and fruit, including releases such as the Orchard Blush rosé cider and ciders made from historic varieties like the Harrison apple. Visitors can stop by the tasting room, open Friday through Monday, to sample the lineup of handcrafted ciders in a relaxed orchard setting. The property also grows and sells heirloom apple trees through its nursery catalog and hosts a range of events and workshops, including live weekend music and seasonal gatherings. With its focus on growing local and drinking local, Albemarle Ciderworks offers a welcoming destination for cider enthusiasts in Central Virginia.

Outdoor SeatingWeddings

• Live Music in the Orchard: Tara MillsSat, Jul 18, 2026, 2:30 PM – 4:30 PM

James River Brewery

James River Brewery is a craft brewery and taproom in Scottsville, Virginia, tucked into the foothills of the Blue Ridge alongside Mink Creek. Award-winning beers are brewed on-site by Head Brewer Darren Queen, with a rotating lineup that spans hoppy IPAs, smooth Hefeweizens, and plenty of styles in between. The tasting room offers a warm, relaxed atmosphere where friendly, knowledgeable staff help visitors find a new favorite among the many brews on tap. Outside, the beer garden hosts live music from musicians across Central Virginia and beyond on weekends, and a fire pit keeps the space comfortable year-round. With its scenic creekside setting and welcoming vibe, James River Brewery is a relaxed gathering spot for craft beer and live music.

Outdoor SeatingFire Pits

No upcoming events listed.

Loving Cup Vineyard & Winery

Loving Cup Vineyard & Winery is a family-owned winery in North Garden, Virginia, distinguished as the only certified-organic vineyard and winery in the state and one of just three on the East Coast. Operating under the motto "Love Is Organic," the winery grows its grapes and produces its wines without synthetic chemicals, and is now celebrating its 15th vintage. Visitors can stop by the tasting room, open Friday through Sunday from 11am to 5pm, to sample the wines and enjoy offerings like seasonal sangria, often while relaxing on the porch overlooking the vineyard. The winery hosts community events on its grounds, including gatherings that benefit local animal sanctuaries and other causes. With its commitment to organic farming and a welcoming, laid-back atmosphere, Loving Cup offers a distinctive stop in the Charlottesville-area wine country.

DogsOutside FoodOutdoor Seating

• Art Exhibit: Barb Wallace – Places Need KeepersFri, May 1 – Sun, Jul 26, 2026
• Art Exhibit: Barb Wallace – Places Need KeepersWed, Jul 1 – Sun, Jul 26, 2026

Pippin Hill Farm & Vineyard

Pippin Hill Farm & Vineyards is a boutique culinary vineyard and all-season events venue set in the scenic foothills of the Blue Ridge Mountains within Virginia's Monticello Wine Region. The estate centers on award-winning estate-grown wines, including whites, reds, and rosés, paired with a garden-to-table culinary program in which the vineyard, garden, farm, and kitchen are seamlessly interwoven to serve fresh, local, and sustainable fare. Visitors can reserve table service in the Tasting Room and deepen their visit with experiences such as the Estate Tour & Tasting, cooking school classes, and other group offerings. The property also offers the Heritage Wine Club, a retail shop with Pippin-approved goods including its #PippinPups line, and gift cards, while a thoughtfully restored 1820s Crossroads Inn just down the hill lets guests extend their stay. Pippin Hill is also a full-service destination for custom-designed weddings and private events, complete with a dedicated culinary team and event services.

B&BDogsOutdoor Seating

No upcoming events listed.

Whitehall Farm & Vineyard

Whitehall Farm & Vineyard is located just south of Charlottesville, Virginia, in the award-winning Monticello viticultural area of Albemarle County. Comprised of 310 gently rolling acres, the farm is home to a vineyard, an equestrian facility, and the South Paddock Winery. Its history dates back to the 1780s, when Southern Albemarle farmland was prized for its proximity to the James River, the superhighway of the 18th and 19th centuries. The farm has evolved over time but retains a gentle, timeless beauty. Visitors are invited to experience the farm on horseback, sip wine at the South Paddock Winery, or host a special event on the grounds. The winery welcomes guests on Saturdays from 1pm to 4pm, with wedding and event tours available by appointment.

Weddings

No upcoming events listed.

Montifalco Vineyard

Montifalco Vineyard is a small, family-run farm winery established in 2016 in Ruckersville, Virginia, within the Monticello American Viticultural Area. Owner and winemaker Justin Falco crafts the wines from grapes grown on site, and the name plays on both the family's "Falco" heritage, meaning hawk or falcon, and the nearby Monticello region. Guests are welcomed Saturdays and Sundays from noon to 5pm for award-winning traditional wine tastings offered in the winery's Cave and Curiosities Gallery by reservation or walk-in. The setting is intentionally relaxed and contemplative, with an emphasis on appreciating the craft of grape growing and winemaking, and the property is also a haven for raptors and birdwatching, from peregrine falcons and red-tailed hawks to its popular goldfinch feeders. A member of the Monticello Wine Trail and several Virginia and international wine associations, Montifalco is an adults-only working farm winery that welcomes outside food outdoors and limits groups to six guests for an unhurried experience.

Outside FoodOutdoor Seating

No upcoming events listed.

Moss Vineyards

Moss Vineyards is a family winery near Nortonsville, Virginia, set on a mountaintop at the doorstep of the Blue Ridge Mountains in the Monticello wine region. The vineyard produces Old World, dry-style wines, including hand-crafted Bordeaux-style blends made from grapes such as Viognier, Cabernet Franc, Cabernet Sauvignon, Merlot, and Petit Verdot, along with a newer gold-medal dry cider. Visitors can take in sweeping mountain views from indoor and outdoor seating areas, available on a first-come basis, and are welcome to bring their own food and seating, though no outside alcohol is permitted. The winery is open Friday through Sunday from noon to 5 and some holiday Mondays, and is dog- and family-friendly with leashed pets and supervised children welcome. A vacation cottage on the property is also available for overnight stays through Airbnb.

DogsFamily FriendlyOutdoor Seating

No upcoming events listed.

Stone Mountain Vineyards

Stone Mountain Vineyards is a family-run winery perched at over 1,700 feet of elevation in Dyke, Virginia, offering some of the most expansive mountain views of any vineyard in the state. Visitors can relax on the property's decks and enjoy wine by the flight, glass, or bottle, with current releases ranging from oak-aged Reserve Chardonnay and crisp stainless-steel Chardonnay to the sweet, refreshing Bacon Hollow Revenuer's Select. The winery welcomes walk-ins without reservations, though parties of eight or more are asked to call ahead. Guests can also arrange tours of the wine processing area and a 120-foot wine cave. Stone Mountain hosts weddings and private events and offers a wine club along with military and wine-industry discounts. Outside food and leashed pets are welcome, making it a relaxed destination for a day in the mountains.

Outdoor SeatingDogsOutside Food

No upcoming events listed.