Events › Crozet & Western Albemarle
The foothills west of Charlottesville — Crozet, White Hall, Free Union, and Greenwood — pack in some of the area's most scenic vineyards, with Blue Ridge views from nearly every tasting-room porch.
Break up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks serving from 4:30–7:30 PM.
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Celebrate summer at the Virginia Sunflower Fest at Chiswell Farm in Greenwood, VA, just outside Charlottesville! Wander through vibrant sunflower fields, capture unforgettable moments with friends & family, and cool off with our refreshing drinks! From sunflower picking to stunning views, it's the ultimate summer escape. Runs Thursdays–Sundays from mid-July through early August, 10 AM–6 PM.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Tailgate Thursdays continue! Thursday, July 16th (6–9 PM). Live Music: Susie + The Pistols. Fresh Eats: Oyster Catcher Sea Farms will be on-site with fresh and grilled oysters on the half shell. The grills are fired up and ready for you!
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An exciting evening of arena polo at the USPA National Sherman Memorial! Established in 1935. Gates open for tailgating at 4 PM, matches begin at 6 PM on July 17.
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A priceless night of rocking good fun featuring KEN FARMER & THE AUTHENTICATORS! From 6 to 8:30pm. Brick City Kitchen Food Truck will be on site. Open to all. No cover.
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Part of Pollak Vineyards' America 250 Series - An Evening with Lucie Morton. A special wine tasting event celebrating America's 250th anniversary.
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An author event featuring Jo Piazza, bestselling author of The Sicilian Inheritance and Everyone Is Lying to You. Ticket purchase required; includes a copy of the book. A propulsive dual-timeline mystery drenched in art-world intrigue.
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Bunch O' Mugs makes their official debut at Glass House Winery & Brewery! This brand new musical blend has been percolating and is ready to be savored. Open to all.
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A fantastic Sunday Funday with music by the Midnight Buzz Duo, featuring the talented husband-and-wife team Tracey and Barry Collins. They deliver a special acoustic performance filled with classic rock favorites. Open to all.
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Tailgate Thursdays continue! Thursday, July 23rd (6–9 PM). Live Music: Moonglow. Fresh Eats: Crozet Seafood will be on-site. The grills are fired up and ready for you! Pack your dancing shoes, favorite grill-ables, lawn games, and picnic blankets.
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Supernova isn't just another tribute band — this six-piece outfit is obsessed with recreating the energy, intensity, and swagger of a live Oasis performance. Free admission.
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Part of Pollak Vineyards' America 250 Series - An Evening with Fred Reno. A special wine tasting event celebrating America's 250th anniversary.
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The Gladstones return to the tropical oasis at Glass House Winery in Free Union! Get ready to rock out to their great rock 'n' roll and original tunes. Open to all.
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The Charlottesville Blues Revue comes to Glass House Winery! This mega-talented lineup features area favorites who have performed on the GHW stage before, but never all together at the same time. Come early! Open to all.
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Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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An incredible musical treat featuring fantastic singer/songwriter John Kelly on guitar and vocals joined by the magnificent harmonica wizard Gary Green. From 2 to 5pm. Open to all. No cover.
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Tailgate Thursdays continue! Thursday, July 30th (6–9 PM). Live Music: Scuffletown. Fresh Eats: Oyster Catcher Sea Farms will be on-site with fresh and grilled oysters on the half shell. The grills are fired up and ready for you!
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Final Fridays Concert at Pollak Vineyards featuring Blake Hunter & the Gatherers. Food truck: Crozet Seafood Supply. Live music under the Blue Ridge skies.
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DON'T LOOK UP features Andy Burdetsky (bass/vocals), Dave Sherman (guitar/vocals), Rob Martin (guitar/vocals), and Lance Foster (drums/vocals) performing Americana music that's deeply rooted in the Blues. Open to all.
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Shotguns N Roses pride themselves on being the most accurate and faithful Guns N' Roses experience you can get! With a powerful frontman and a ferocious band, they bring all the classic outfits, instruments and stage props from GNR 1987–1993. GA tickets $20 presale / $25 door. VIP Tables available (21+).
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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On Saturday, 8/8 at 7 PM, Crown Club members will be enjoying light plates freshly made from Chiles Peach Orchard's seasonal harvest.
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A triple-bill featuring guitarist Isaac Hadden, John Daniel Ray (progressive jazz bassist and composer), and legendary fusion drummer Jeff Sipe. An evening of exploratory improvised music.
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Blasting out of the Tri-State area (NY, NJ, PA), Obey Your Master performs a full catalog of Metallica hits from Kill 'Em All to 72 Seasons. The most authentic, face-melting Metallica tribute show around.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, September 7, 2026.
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On Saturday, 9/12 at 6:30 PM, Crown Club members will take a pre-harvest look at the crop before engaging in some old-fashioned grape stomping!
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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DMTB is a celebration of the music of the Dave Matthews Band — a time machine to the 90s with complex guitar riffs, soaring violin melodies, smooth sax lines, and explosive drumming. Buffalo, NY based band with 2000+ shows in 46 states and 10 countries.
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Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Set sail on a groovy voyage through the smooth sounds of the 70s and 80s! Thurston Howell crafts a symphony of classic hits from Toto, Michael McDonald, Hall & Oates, and Steely Dan. Because You Can't Fake SMOOTH!
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Full Moon Fever is back for an epic Tom Petty party celebrating the birthday of Tom Petty and the 50th anniversary of American Girl! Performing all your favorite Petty hits with high-energy authenticity.
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Crown Club members and their guests will be guided through these sweet pairings by Gearharts Fine Chocolates. Advance registration is requested.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Pandora's Box Tribute has been rocking stages across the US and internationally since 2015. They'll take you on a high-octane journey through 50 years of mega hits from one of the world's most iconic rock bands.
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Crown Club members and guests are invited to solve Chiswell's murder mystery, starting at 5:30 PM on Saturday, November 14.
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Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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Members of our wine club and their guests will be exchanging gifts during a special holiday celebration on Saturday, December 12!
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Join us for live music, Christmas cookies, and traditional mulled wine at our holiday open house on Friday, December 18.
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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
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
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
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.
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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
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.
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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
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
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
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.
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