Winery Events in Barboursville, Orange, Madison & Greene

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

• Trivia NightThu, Sep 10, 2026, 6:30 PM – 8:30 PM
• The UnsuitablesSat, Sep 12, 2026, 6 PM – 9 PM
• Trivia NightThu, Sep 17, 2026, 6:30 PM – 8:30 PM

+ 3 more upcoming events →

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

• Labor Day Music with Smokin' Trout plus Grill & ChillMon, Sep 7, 2026, 2 PM – 5 PM
• Friday Night Out with John Kelly & Half Price Wine FlightsFri, Sep 11, 2026, 5 PM – 8 PM
• Celebrate the Norton Grape: Norton Mini Fest at DuCardSat, Sep 12, 2026, 12 PM – 5 PM

+ 11 more upcoming events →

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

• An Evening with Chef Patrick O'Connell: New Memoir CelebrationSun, Sep 13, 2026, 4 PM – 8:30 PM
• Taste of Virginia: Wine & Food Grand TastingSun, Oct 4, 2026, 1 PM – 4 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

• Wine & Design at Horton Vineyards with Monica Garrett InteriorsSat, Oct 24, 2026, 3 PM – 6 PM

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.

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

• The Art of The Container GardenSat, Sep 12, 2026, 10 AM
• The Art of The Low Maintenance Garden & Building a Winter Interest GardenSat, Sep 19, 2026, 10 AM
• Pumpkin Decorating WorkshopSat, Sep 26, 2026, 10 AM

+ 6 more upcoming events →

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

No upcoming events listed.