Local Event Premier Host

The Big Cheese Festival

Cost: $20 Advance / $25 Gate

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!

Tags

• event
• wine and cheese
• local
• family fun
• wine
• cheese
• goats
• music
• vendors
• Things to do in Winchester, VA
• Virginia Wine & Food Events
• Winchester Wine & Food Events