September 2026
Fall at Eastwood
September is the perfect time to savor the changing season at Eastwood. Join us for Oyster Fridays, Eastwood After Dark, and live music every week. Plus, Oktoberfest returns to the winery and we will be hosting special events including our annual Oktoberfest Artisan Market, the Charlottesville Chamber Music Festival, and more.
Labor Day Weekend
September 4 – September 7
Join us for the ultimate long weekend celebration featuring fresh oysters, award winning wines, and vibrant live music.
Friday, September 4
Virginia Oyster & Wine Celebration – Salty Bottom Blue
Live Music – FarAway 5-8PM
Saturday, September 5
Live Music All Day – Drew LeBlanc 12:30-3:30PM and Transatlantic Invasion 5-8PM
Sunday, September 6
Live Music: John Benjamin 1-4PM
Monday, September 7
Labor Day: Open 12-5PM
Charlottesville Chamber Music Festival Concert
Wednesday, September 16
As evening settles over the winery, this concert offers an inviting journey through the sound world of American composers. With light fare and beverages available for purchase beforehand beginning at 6:00pm, the experience combines conviviality and contemplation—beautiful music unfolding in a cozy space designed for listening and lingering. Eastwood is about 5 miles south of Charlottesville.
Doors open at 6:00pm for food and beverage purchases, music begins at 7:30pm.
Virginia Oyster & Wine Celebration
Every Friday
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
September 11: John Kelly
September 18: Matthew O’Donnell
September 25: Sue Harlow
Reservations are not needed to visit the winery. Join us for oysters, wine, and live music Friday evenings!
Live Music & Music Bingo
Thursday – Sunday Every Week
Join us for the popular Eastwood After Dark featuring upbeat, danceable music on Saturday nights from 5-8pm (in addition to our more mellow Saturday afternoon music program). Eastwood also hosts a range of live performances by talented local and regional musicians every Thursday and Friday night and many Sundays. See Winery Calendar For Details
