Music Bingo @Eastwood 2-4PM

Sunday, May 31, 2026, 2:00 PM – 4:00 PM

Sunday Session @Chisholm Vineyard- Robert Jospé Trio 1-4pm

Sunday, May 31, 2026, 1:00 PM – 4:00 PM

L. Scott Benefit Dinner @Michael Shaps with Public Fish & Oyster House

Saturday, May 30, 2026, 6:00 PM – 9:00 PM

Live Music @Eastwood feat Brian Franke 12:30-3:30PM Eastwood After Dark feat Live Music by Kat & The Travelers 5-8PM

Saturday, May 30, 2026, 12:30 PM – 8:00 PM

French-Bistro Supper Series @Veritas Vineyards & Winery

Friday, May 29, 2026, 6:30 PM – 8:30 PM

Friday Sunset Soirée @Chisholm Vineyard- Ken Farmer & the Authenticators with Two Brothers Southwestern Grill 6-9pm

Friday, May 29, 2026, 6:00 PM – 9:00 PM

Virginia Oyster & Wine Celebration @Eastwood 5-8PM Live Music feat Sharif 5-8PM

Friday, May 29, 2026, 5:00 PM – 8:00 PM

Tailgate Thursdays at Stinson Vineyards

Thursday, May 28, 2026, 6:00 PM – 9:00 PM

Bonus Session Sunday at Stinson Vineyards

Sunday, May 24, 2026, 1:00 PM – 4:00 PM

Sunday Session @Chisholm Vineyard- The Elswick Gathering 1-4pm

Sunday, May 24, 2026, 1:00 PM – 4:00 PM

Live Music @Eastwood feat Sue Harlow 12:30-3:30PM

Saturday, May 23, 2026, 1:00 PM – 4:00 PM

Friday Sunset Soirée @Chisholm Vineyard- 180 Band with Twisted Provisions 6-9pm

Friday, May 22, 2026, 6:00 PM – 9:00 PM

Virginia Oyster & Wine Celebration @Eastwood 5-8PM Live Music feat Rusty Spiedel & Tom Goodrich 5-8PM

Friday, May 22, 2026, 5:00 PM – 8:00 PM

Tailgate Thursdays at Stinson Vineyards

Thursday, May 21, 2026, 6:00 PM – 9:00 PM

Sunday Session @Chisholm Vineyard- The Trio 1-4pm

Sunday, May 17, 2026, 1:00 PM – 4:00 PM

Live Music @Eastwood feat Ramona Martinez 1-4PM

Sunday, May 17, 2026, 1:00 PM – 4:00 PM

Vertical Tasting Experiences @Michael Shaps Winery

Sat, May 16, 2026, 2:00 PM – Sun, May 17, 2026, 2:00 PM

Live Music @Eastwood feat Anthony Semiao 12:30-3:30PM Eastwood After Dark feat Live Music by The Wavelength 5-8PM

Saturday, May 16, 2026, 12:30 PM – 8:00 PM

Friday Sunset Soirée @Chisholm Vineyard - Chickenhead Blues with CubaMex 6-9pm

Friday, May 15, 2026, 6:00 PM – 9:00 PM

Virginia Oyster & Wine Celebration @Eastwood 5-8PM Live Music feat Matthew O'Donnell 5-8PM

Friday, May 15, 2026, 5:00 PM – 8:00 PM

Mother’s Day Sunday Session @ Chisholm Vineyard

Sunday, May 10, 2026, 1:00 PM – 4:00 PM

Mother's Day Market @Eastwood 12-5PM Live Music feat Vicky Lee 1-4PM

Sunday, May 10, 2026, 12:00 PM – 5:00 PM

Sip & Bloom: A Mother’s Day Wine + Bouquet Workshop @Chestnut Oak

Sat, May 9, 2026, 1:00 PM – Sun, May 10, 2026, 3:00 PM

Chestnut Oak

Live Music @Eastwood feat FarAway 12:30-3:30PM Eastwood After Dark feat Live Music by Classic Road 5-8PM

Saturday, May 9, 2026, 12:30 PM – 8:00 PM

Charlottesville Arts Collective Pop-Up Market @Blenheim Vineyards

Saturday, May 9, 2026, 11:00 AM – 4:00 PM

Friday Sunset Soirée @ Chisholm Vineyard- Scuffletown with Arepas on Wheels 6-9pm

Friday, May 8, 2026, 6:00 PM – 9:00 PM

Virginia Oyster & Wine Celebration @Eastwood 5-8PM Live Music feat John Kelly 5-8PM

Friday, May 8, 2026, 5:00 PM – 8:00 PM

Sunday Session @ Chisholm Vineyard- Mirabelle & Matty Metcalfe 1-4pm

Sunday, May 3, 2026, 1:00 PM – 4:00 PM

Live Music feat Mike & Barry 12:30-3:30PM Eastwood After Dark feat Live Music by Spiedel, Goodrich & Friends 5-8PM

Saturday, May 2, 2026, 12:30 PM – 8:00 PM

Friday Sunset Soirée @ Chisholm Vineyard- Zuzu’s Hot Five with Sweet Jane’s Kitchen 6-9pm

Friday, May 1, 2026, 6:00 PM – 9:00 PM

Virginia Oyster & Wine Celebration @Eastwood Farm & Winery 5-8PM Live Music feat Eli Cook 5-8PM

Friday, May 1, 2026, 5:00 PM – 8:00 PM

Sip & Thrift @Horton Vineyards

Mon, Mar 16, 2026, 12:30 PM – Fri, May 15, 2026, 1:30 PM

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