The Big Cheese Festival

Schedule

Sat Oct 24 2026 at 12:00 pm to 06:00 pm

UTC-04:00
Location

James Charles Winery & Vineyard | Winchester, VA

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Come get cheesy at James Charles Winery on October 24, 2026! The Big Cheese Festival is a full day of wine, live music, local vendors, food trucks and, of course, plenty of cheese.

Your ticket includes festival entry plus one wine and cheese pairing of your choice at one of our three winery tents: James Charles Winery, Veramar Vineyard or Bogati Winery. Each pairing includes three wines paired with three cheese samples. Additonal pairings will be for purchase at each winery tent.

Enjoy live music from singer-songwriter Nate Hadley from 12:00–2:00 PM, followed by local favorite The Cruisers from 2:00–5:00 PM.

Explore cheese and wine pairings, shop from local crafters and businesses, and meet adorable baby goats. Featured vendors include Fleur de Lis Cheese Shop, Harvue Cheese and Farm, Uncle Beehive Ice Cream, Fireside Pizza, and Blue Ridge Popcorn Company, serving assorted popcorn flavors and dirty sodas—with even more vendors to be announced!

Tickets

$20 in advance

$25 at the door

Children under 12 are free

No pets or coolers are permitted.

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Where is it happening?

James Charles Winery & Vineyard, 4063 Middle Rd, Winchester, VA 22602, United States

Event Location & Nearby Stays:

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James Charles Winery & Vineyard
Host or PublisherJames Charles Winery & Vineyard

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