Wineries Events Retailers About Guide Blog

The Big Cheese Festival

Event Date

Saturday, October 24, 2026
12:00pm - 6:00pm

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

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 pet 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.

Other Events Hosted by this Winery

Location

4063 Middle Rd
Winchester, VA 22602
Get Directions
Event Fee

$20

Contact Person

James Charles Winery

Contact Phone

5409314386

Contact Email

info@jamescharleswine.com

Website

Categories

Festival

Wine & Food Pairing

Winery Concert / Entertainment

Wine Tasting