Events › Festivals

Wine, Beer & Harvest Festivals near Charlottesville

Harvest parties, crush festivals, oyster roasts, and multi-winery celebrations — Charlottesville wine country's festival season runs nearly year-round. Plan your next big day out here.

Festivals this weekend Oct 30–Nov 1

Upcoming festivals

East End Fair at Southwest Mountains Vineyards
Festival

East End Fair

Sat, Nov 14, 2026
12:00 PM – 5:30 PM

Join us for a day-long celebration of Virginia country life, inspired by the grand countryside fairs of the UK. Enjoy tastings from local wineries, breweries, and distilleries, live music, field sports, artisan vendors, and more — all set against the rustic beauty of Keswick horse country. Held at East End Farm, 292 Hamilton Rd, Louisa, VA. More info: https://www.smvwines.com/east-end-fair

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Recent past events

Hallowine at Southwest Mountains Vineyards
FestivalPast

Hallowine

Sat, Oct 24, 2026
11:00 AM – 5:30 PM

Join us for a festive day of wine, music, and Halloween spirit at the vineyard! We'll have plenty of family friendly activities, including apple bobbing, pumpkin painting, live music, a kids' costume contest parade, face painting, and more!

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Horton on the Go: Town Point Virginia Fall Wine Festival at Horton Vineyards
FestivalPast

Horton on the Go: Town Point Virginia Fall Wine Festival

Sat, Oct 17 – Sun, Oct 18, 2026
12:00 PM

Horton on the Go: find Horton Vineyards at the 38th Annual Town Point Virginia Fall Wine Festival, Saturday & Sunday, October 17-18, 2026, at Town Point Park on the Downtown Norfolk Waterfront (113 Waterside Drive, Norfolk). More than 25 of the Commonwealth's top wineries pour over 200 wines. Off-site event; all-day listing on Horton's calendar.

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FAQ

Where can I find festivals in Charlottesville this weekend?

3 festivals events are listed this weekend (Oct 30–Nov 1): Blue Ridge Mountain Maze Corn Maze & Fall Festival at Blue Toad Hard Cider (Sat 10 AM); Halloween at Brewing Tree at Brewing Tree Beer Company (Sat 12 PM); Blue Ridge Mountain Maze Corn Maze & Fall Festival at Blue Toad Hard Cider (Sun 10 AM).

What festivals events are coming up near Charlottesville?

7 upcoming festivals events at area wineries, breweries and cideries, including Blue Ridge Mountain Maze Corn Maze & Fall Festival at Blue Toad Hard Cider (Sat 10 AM); Halloween at Brewing Tree at Brewing Tree Beer Company (Sat 12 PM); Blue Ridge Mountain Maze Corn Maze & Fall Festival at Blue Toad Hard Cider (Sun 10 AM); Blue Ridge Mountain Maze Corn Maze & Fall Festival at Blue Toad Hard Cider (Sat 10 AM); Apple Harvest Festival at Albemarle Ciderworks (Sat 10 AM); plus 2 more.

Which Charlottesville venues host the most festivals events?

Blue Toad Hard Cider (4), Brewing Tree Beer Company (1), Albemarle Ciderworks (1), Southwest Mountains Vineyards (1) have the most upcoming festivals events.

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