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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.

Eastwood Farm and Winery is a winery in Charlottesville, Virginia, part of the Charlottesville area of Charlottesville wine country. Amenities include dogs, family friendly, outdoor seating, weddings. There are 37 upcoming events on the calendar — see the full list below, or browse more events in the area on the events calendar. Explore more of Charlottesville.


Upcoming events at Eastwood Farm and Winery

Chili Night with Live Music: John Kelly at Eastwood Farm and Winery
Food

Chili Night with Live Music: John Kelly

Fri, Nov 6, 2026
5:00 PM – 8:00 PM

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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Lockjaw Classic Rock 🎺 | Eastwood After Dark at Eastwood Farm and Winery
Music

Lockjaw Classic Rock 🎺 | Eastwood After Dark

Sat, Nov 7, 2026
5:00 PM – 8:00 PM

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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Live Music: Porch Dogs at Eastwood Farm and Winery
Music

Live Music: Porch Dogs

Sat, Nov 14, 2026
12:30 PM – 3:30 PM

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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Music Bingo at Eastwood Farm and Winery
Trivia

Music Bingo

Sun, Nov 15, 2026
2:00 PM – 4:00 PM

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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Thanksgiving Eve Gathering at Eastwood Farm and Winery
Community

Thanksgiving Eve Gathering

Wed, Nov 25, 2026
12:00 PM – 8:00 PM

Kick off Thanksgiving at Eastwood! Join us the Wednesday before Thanksgiving for live music, delicious oysters from Salty Bottom Blue, and a glass of your favorite Eastwood wine. Enjoy fresh oysters on-site or pick up your Thanksgiving oyster preorder.

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Chili Night 🫘 at Eastwood Farm and Winery
Food

Chili Night 🫘

Fri, Nov 27, 2026
5:00 PM – 8:00 PM

Warm up your Friday nights with Chili Night at Eastwood: every Friday 5–8 p.m., hearty chili, homemade cornbread and all the fixings, with meat and vegetarian options. Enjoy wine, games and music. Full menu also available.

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Paint & Sip at Eastwood Farm and Winery
Workshop

Paint & Sip

Sun, Nov 29, 2026
12:00 PM – 2:00 PM

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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Music Bingo at Eastwood Farm and Winery
Trivia

Music Bingo

Sun, Nov 29, 2026
2:00 PM – 4:00 PM

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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Chili Night 🫘 at Eastwood Farm and Winery
Food

Chili Night 🫘

Fri, Dec 4, 2026
5:00 PM – 8:00 PM

Warm up your Friday nights with Chili Night at Eastwood: every Friday 5–8 p.m., hearty chili, homemade cornbread and all the fixings, with meat and vegetarian options. Enjoy wine, games and music. Full menu also available.

More Info
Santa Is Coming To Town at Eastwood Farm and Winery
Family

Santa Is Coming To Town

Sun, Dec 6, 2026
12:00 PM – 5:00 PM

Join us for a special visit from Santa! Plus, holiday milk and cookies flights are back by popular demand for the kids. Indoor event with opportunities to take your own photos with Santa. No cost to visit Santa.

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Music Bingo at Eastwood Farm and Winery
Trivia

Music Bingo

Thu, Dec 10, 2026
6:00 PM – 8:00 PM

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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Holiday Market at Eastwood Farm and Winery
Seasonal

Holiday Market

Sat, Dec 12, 2026
12:00 PM – 4:00 PM

Browse local vendors, enjoy delicious food and drinks, sip on milk and cookie flights, and soak up the holiday spirit with live music! Market 12-4PM; Holiday Carols 12:30-3:30PM.

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Santa Is Coming To Town at Eastwood Farm and Winery
Family

Santa Is Coming To Town

Sun, Dec 13, 2026
12:00 PM – 5:00 PM

Join us for a special visit from Santa! Plus, holiday milk and cookies flights are back by popular demand for the kids. Indoor event with opportunities to take your own photos with Santa. No cost to visit Santa.

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Santa Is Coming To Town at Eastwood Farm and Winery
Family

Santa Is Coming To Town

Sun, Dec 20, 2026
12:00 PM – 5:00 PM

Join us for a special visit from Santa! Plus, holiday milk and cookies flights are back by popular demand for the kids. Indoor event with opportunities to take your own photos with Santa. No cost to visit Santa.

More Info
Paint & Sip at Eastwood Farm and Winery
Workshop

Paint & Sip

Sun, Dec 27, 2026
12:00 PM – 2:00 PM

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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