Winery Events in Charlottesville, Virginia

Live Music: Chris Hammock

Virginia Oyster & Wine Celebration with Live Music: Matthew O’Donnell

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 September 4: FarAway | 5-8PM September 11: John Kelly | 5-8PM September 18: Matthew O’Donnell | 5-8PM September 25: Sue Harlow | 5-8PM October 2: Eli Cook | 5-8PM October 9: John Kelly | 5-8PM October 16: Matthew O’Donnell | 5-8PM October 23: Matthew O’Donnell | 5-8PM

Sunset Soirée - Chickenhead Blues with Twisted Provisions

Friday Sunset Soirée live music with Chickenhead Blues, food by Twisted Provisions.

Harvest Nights at the Collective + Winemaker Pop-Up: Joy Ting

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 Joy Ting — free samples and a facility tour with one of the Collective's independent winemakers.

Harvest Party Oyster Roast

Raise a glass of award-winning Eastwood wine to harvest season! Join us at Eastwood Farm and Winery on Saturday, October 17, for our Harvest Party Oyster Roast, part of a celebration of Virginia wine across the Commonwealth. Gather your friends, sip your favorite Eastwood wines, and enjoy a special menu by Salty Bottom Blue, featuring oysters Rockefeller, crab cakes, grilled oysters, and oysters raw on the half shell. Eastwood’s full menu will also be available all day, from 12–7:30 PM. Make a day of it with live music by Heidi Riddell from 12:30–3:30 PM and The Wavelength from 5–8 PM! It’s a day to celebrate the season and the people, places, and flavors that make Virginia wine special.

Live Music: Heidi Riddell

Come see Heidi Riddell! Heidi will be playing from 12:30-3:30PM.

Matthew O’Donnell Music

Live music from Matthew O’Donnell in the Hark Vineyards tasting room, with estate-grown, Governor's Cup gold medal wines.

The Wavelength 🎺 | Eastwood After Dark

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. Saturday Night Music Lineup: September 5: Transatlantic Invasion | 5-8PM September 12: LockJaw | 5-8PM September 19: The Wavelength | 5-8PM September 26: Kat & The Travelers | 5-8PM October 3: The Unsuitables | 5-8PM October 10: Jason Burke: Bunch O’Mugs | 5-8PM October 17: The Wavelength | 5-8PM October 24: Classic Road | 5-8PM Check back for more dates this fall!

Stage Fright! An Improv Comedy Show

Celebrate spooky season with a night of completely unscripted comedy inspired by audience suggestions at Vinegar Hill Theatre (Lighthouse Studio, 220 W Market St). Featuring members of Goat Rodeo's improv teams Big Head Fight and Billionaire Robot Dogs. $10 advance, $15 at the door.

Fall Family Day & Harvest Party Market

Sunday Session - The Trio

Sunday Session live music with The Trio.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Live Music: Brian Franke

Come see Brian Franke! Brian will be playing from 1-4PM.

Live Music: Joel Streeter

Spooky Halloween Trivia

Halloween-themed Monday trivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

An Evening of Hope

Evening of Hope: A Community Celebration & Fundraiser October 21, 2026 | 6:00–9:00 PM Eastwood Farm and Winery Join us for Reclaimed Hope’s annual community celebration and fundraiser, where friends, families, and supporters come together for a memorable evening with purpose.

Porch Nights: Ty Burkhardt ✨

Come see Ty Burkhardt from 5-8PM! Porch Nights at Eastwood ✨ There’s something about a porch at golden hour that makes the world slow down in the best possible way. At Eastwood Farm and Winery, we’re leaning into that feeling all season long with Porch Nights — our weekly Thursday gathering featuring outdoor live music and an easygoing atmosphere. Grab a seat on our covered veranda or at one of our many picnic tables, relax with the sparkly lights overhead, fireflies in the fields, and a glass of porch-sipping wine in hand – join us for your new favorite Thursday tradition.

Paint + Sip at the Virginia Wine Collective

Come paint with us, no experience necessary, all materials included! Your ticket includes a canvas, specialty paint, and all supplies. Each class is taught by a professional artist who will guide you through the design step by step at a comfortable pace. Ticketed event.

Fresh Pour Thursday

A new beer is tapped at 6:30 PM every Thursday at Three Notch'd Charlottesville, with a free taste.

Live Music: Sue Harlow

Virginia Oyster & Wine Celebration with Live Music: Matthew O’Donnell

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 September 4: FarAway | 5-8PM September 11: John Kelly | 5-8PM September 18: Matthew O’Donnell | 5-8PM September 25: Sue Harlow | 5-8PM October 2: Eli Cook | 5-8PM October 9: John Kelly | 5-8PM October 16: Matthew O’Donnell | 5-8PM October 23: Matthew O’Donnell | 5-8PM

Fall Wine Dinner w/Chef Rachel Pennington

A ticketed fall wine dinner at Hark Vineyards prepared by Chef Rachel Pennington and paired with Hark's estate wines. Tickets via Ticket Tailor.

Friday Sunset Soirée - Big Fun with Sweet Jane's Kitchen

Friday Sunset Soirée live music with Big Fun, food by Sweet Jane's Kitchen.

Harvest Nights at the Collective

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.

Halloween Scavenger Hunt

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!

Live Music: FarAway

Come see FarAway! FarAway will be playing from 12:30-3:30PM on the stage in The Barn.

Live Music: Matty & Mirabelle

Five Old Gentlemen (FOG) Live

Join us at Blenheim Vineyards on Saturday, October 24 from 3–5 PM for an afternoon of free live music with Five Old Gentlemen (FOG), a classic rock band covering tunes from the '50s to the '90s. Settle in under the tent overlooking the vineyard, grab a glass or bottle of Blenheim wine, and enjoy a fall afternoon of live music, good company, and vineyard views. Free admission | No reservations required

The Norms Music

Live music from The Norms at Hark Vineyards, with estate-grown wines and mountain views.

Classic Road 🎺 | Eastwood After Dark

Come see Classic Road! They will be playing from 5-8PM. 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.

Fall Sound Bath

A restorative one-hour Fall Sound Bath in the Center at Oakencroft with light stretching and meditation. $34 per ticket.

Guided Farm & Vineyard Walk

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.

Paint & Sip “Garden Ghost”

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.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Sunday Session - The Michael Elswick Gathering

Sunday Session live music with The Michael Elswick Gathering.

Allie Kelly – Artist Meet & Show

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.

Music Bingo

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!

Trivia w/ Olivia

Monday trivia with Olivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

Karaoke Night

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+.

Fresh Pour Thursday

A new beer is tapped at 6:30 PM every Thursday at Three Notch'd Charlottesville, with a free taste.

Live Music: Bob & Kenn

Virginia Oyster & Wine Celebration with Live Music: Lenny Burridge

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.

Sunset Soirée - Richelle Claiborne & Friends with Two Brothers Southwestern Grill

Friday Sunset Soirée live music with Richelle Claiborne & Friends, food by Two Brothers Southwestern Grill.

Harvest Nights at the Collective + Winemaker Pop-Up: Josh Cataldo

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.

Halloween at Eastwood 🎃

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.

Eastwood After Dark: Halloween Edition 👻

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.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Live Music: Chris Hammock