Events › Charlottesville
In & around town · 0–15 min from Charlottesville
Charlottesville sits at the center of the Monticello AVA, with tasting rooms, urban wineries, and cideries minutes from downtown. Live music, trivia nights, and tastings run all week — no long drive required.
Hark's annual Halloween scavenger hunt in the vineyard, Oct 24–25. Follow clues through the vines to uncover spooky items hidden across the property. Wine for 21+, goodie bags for the kids. Costumes encouraged!
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A restorative one-hour Fall Sound Bath in the Center at Oakencroft with light stretching and meditation. $34 per ticket.
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A leisurely guided stroll through Oakencroft's vineyards, orchard and pastures: scenic views, farm animals and the sustainable practices behind the wines, followed by a complimentary glass of wine or seasonal sangria. $22 per ticket.
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Come paint with us, no experience necessary, all materials included! Instructor: Catelyn With your ticket, you get all painting materials, an 11×14 canvas, and a fun time with friends! Join us to learn how to paint this design in a step by step format. Each class is taught by a professional artist that will guide you through various techniques at a comfortable pace. Ticketed event.
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Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.
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Sunday Session live music with The Michael Elswick Gathering.
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Join us in the tasting room at Blenheim Vineyards and meet the artist, Allie Kelly, October 25th from 2-4pm. Her artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights. About Allie: Residing in Buckingham County, Virginia, Allie Kelly is an artist living in her garden. Painting from nature, daily appreciation and observations lead to works in oil, watercolor, and natural pigment. Hidden beauty and a sense of wonder are found and portrayed in her brush strokes.
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Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!
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Monday trivia with Olivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.
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Join us for karaoke night at the Virginia Wine Collective in the loft! Grab a drink, bring your friends, and take the mic for a night of fun, music, and great vibes. Karaoke is hosted 7-9PM, the Collective will be open 5-10PM! 21+.
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A new beer is tapped at 6:30 PM every Thursday at Three Notch'd Charlottesville, with a free taste.
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Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season. Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood. Live music by Lenny Burridge, 5-8PM.
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Friday Sunset Soirée live music with Richelle Claiborne & Friends, food by Two Brothers Southwestern Grill.
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Experience Virginia wine country during its most exciting season. Join us on Friday evenings throughout harvest for a behind-the-scenes look at what happens when grapes begin their journey to becoming wine. Also tonight: Winemaker Pop-Up with Josh Cataldo — free samples and a facility tour with one of the Collective's independent winemakers.
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Celebrate Halloween at Eastwood with a fun afternoon for the whole family! Join us on Saturday, October 31 from 12–4 PM for live music, Halloween treats, kids’ activities, and plenty of festive fun. Kids are invited to come dressed in their favorite costumes for our costume parade and prizes, while parents can enjoy a glass of wine, cider, or beer and a bite to eat.
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Halloween is taking over Eastwood! Put on your best costume and join us for an evening of swing dancing, live music, wine, and Halloween fun. Swing Cville will kick things off with a swing dance lesson at 4 PM, followed by live music from Zuzu’s Hot 5 from 5–8 PM. Costumes are highly encouraged! Show off your Halloween spirit in our costume contest, with prizes for the best looks.
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Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.
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Get ready for a night of big laughs and great wine! Comedy Uncorked is coming to Eastwood Farm and Winery for an evening of live stand-up comedy in the vineyard.
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Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season. Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood. Live music by John Kelly, 5-8PM.
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Friday Sunset Soirée live music with The Inclinators, food by Two Brothers Southwestern Grill.
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Come see Jim Richardson! Jim will be playing from 12:30-3:30PM.
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Come see Lockjaw! They will be playing from 5-8PM. About Lockjaw: Crowd-pleasing classic rock and blues. Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.
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Come see Brian Franke! Brian will be playing from 1-4PM.
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Join us for karaoke night at the Virginia Wine Collective in the loft! Grab a drink, bring your friends, and take the mic for a night of fun, music, and great vibes. Karaoke is hosted 7-9PM, the Collective will be open 5-10PM! 21+.
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Come see Sue Harlow! Sue will be playing from 5-8PM.
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Come see the Porch Dogs! They will be playing from 12:30-3:30PM. About Porch Dogs Porch Dogs Keith and Everette have been entertaining Central and Southwest Virginia for over seven years with a variety of music from mellow to rocking. Pop, Rock, Americana, Soul, Country and Oldies. These dogs do it all!
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Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.
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Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!
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Beginner-friendly Mahjong lessons with Mountain Mahj: learn the rules, strategies, and traditions of the game in easy-to-follow steps while hanging out with friends. Lesson is 2.5 hours. Ticketed event (mountainmahjczt.com/classes).
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A restorative evening sound bath by candlelight in the Center at Oakencroft. $34 per ticket.
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Come see Matthew O’Donnell! Matthew will be playing from 5-8PM.
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Come see Heidi Riddell! Heidi will be playing from 12:30-3:30PM.
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Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.
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Sip, create, and get into the holiday spirit at our workshop where you can make your very own one of a kind festive wreath! Ticketed event.
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Come see FarAway! FarAway will be playing from 1-4PM on the stage in The Barn.
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Come see Lenny Burridge! Lenny will be playing from 12:30-3:30PM.
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Eastwood Farm and Winery is hosting our first-ever Young Makers Market on Saturday, November 28 — featuring kid and teen artisan vendors selling handmade goods just in time for the holidays!
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Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food.
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Come paint with us, no experience necessary, all materials included! Instructor: Catelyn. Ticket includes all painting materials and an 11×14 canvas. Ticketed event.
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Join us in the tasting room at Blenheim Vineyards and meet the artists, Virginia Rieley & Eliza Evans, Sunday, November 29th from 2-4pm. Their artwork will be on display and available for purchase. We will have snacks and wine for sale by the glass, bottle, and flights. Eliza Evans & Virginia Rieley grew up in North Garden near Charlottesville and have been friends since childhood, collaborating artistically for over 35 years. Eliza paints acrylic portraits from life, usually in a single sitting; Virginia is a mixed media collage artist who combines her own photography with watercolor and pen to create layered scenes of local places. Together they co-create the hand-drawn Every Day is a Holiday Calendar, self-published each year since 2006.
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Join Hope Henderson of Flora Design for a holiday wreath-making afternoon with Oakencroft wine. $90 per ticket.
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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.
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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.
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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.
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Gabriele Rausse Winery is the small, family-run winery of Gabriele Rausse, the Italian-born winemaker widely credited as a founding figure of the modern Virginia wine industry. Tucked into the woods on Carter's Mountain Road just a few minutes from Monticello, Jefferson Vineyards, and Highland, the winery makes hand-crafted, small-production, dry European-style wines, including sparkling, red, white, and rosé, along with its Vino dal Bosco label. The tasting room is open Thursday, Friday, Sunday, and Monday; tastings are $16 and come with complimentary homemade sourdough bread, with local cheese from Caromont Farm available and outside food welcome. All seating is outdoors with limited standing room at the bar, so check the weather before you go. Dogs are welcome. The winery also offers A Set of Six, a wine subscription with pickup at special events or shipping.
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Goat Rodeo Comedy Co. presents bold, character-driven long-form improv at monthly shows in Charlottesville and beyond, with scenes and stories built entirely from an audience suggestion. Shows are staged at Vinegar Hill Theatre.
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.
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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.
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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.
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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.
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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.
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The Virginia Wine Collective is Eastwood Farm and Winery's urban wine production facility and tasting room on Avon Street Extended in Charlottesville, about three miles from the Eastwood farm and across from the Wegmans shopping center. Opened in May 2025, it houses nine private winemaker suites and an incubator program that give independent winemakers a home base in the Monticello AVA. The tasting room and kitchen are open Wednesday through Friday evenings with thin-crust pizzas, shareable plates, Winemaker Wine Flights, cold beer on tap, a lounge and shuffleboard. Regular events include Wednesday karaoke, Friday winemaker pop-ups, Harvest Nights, Mahjong lessons and paint-and-sip classes. Guests must be 21+ with valid ID.