5800 Wessex Hundred
Williamsburg, VA 23185
LIVE MUSIC – 1619 Pavillion
Country music is coming back to the vineyard, and this year’s lineup has a hometown feel. Cannon Country 107.9 FM and The Williamsburg Winery are bringing back Cannon Country Fest on Saturday, August 1, and 2026 marks the festival’s return to Williamsburg. Headlining the show is Williamsburg native Canaan Smith, joined by a lineup of local artists who know how to get a crowd going—including Cawson’s Coop Band. If your cowboy boots have been collecting dust, now’s a good excuse to pull them back out.
Live Music Schedule
2:00 PM – Sam Riddle
3:30 PM – Lane Rice
5:00 PM – Cawson’s Coop Band
6:30 PM – Canaan Smith
Bring a lawn chair or blanket, grab a spot on Wessex Lawn, and settle in for an afternoon of live country music surrounded by the vineyard. Between sets, sample award-winning Virginia wines, local craft beer and cider, and plenty of food from onsite vendors. It’s one of those summer events that’s just easy—good music, good wine, and a great excuse to spend the day outside.
General Admission
First-come, first-served seating on Wessex Lawn
Kids 12 and under are free
Free parking
VIP (21+ Saturday Only)
If you’d rather skip the crowds, VIP includes:
Preferred seating with the best views
Commemorative wine glass
Complimentary wine pour
Private VIP bar
Private restrooms
Free parking
Get your tickets before they’re gone—this one tends to draw a crowd.
About the Venue
The 1619 Wine Pavilion is a great place for you and your guests to enjoy fantastic wine in a comfortable and relaxed setting. The Pavilion features a staffed wine bar where you can order wine by the flight, glass, or bottle. While the Pavilion is not a restaurant, food can be ordered to-go from the Gabriel Archer Tavern and enjoyed on the Pavilion. Don’t miss the cheese platter. ​ This is Williamsburg Virginia and the venue would be incomplete without some historic relevance. The 1619 Wine Pavilion was named in honor of the 400th Anniversary of the Acte 12 of 1619 which “required all landowners to plant and maintain 10 grapevines for the purpose of making wine in Colonial Virginia.”
Find More Local Gigs:Â WilliamsburgVisitor.com Live Music Finder
