2026 Windsor Fair Entertainment
Headlining with Chris Cagle LIVE, the Black Cat Hell Driver’s Stunt Auto Thrill Show, the Maine State Truck & Tractor Pull, Demolition Derby, and Peter Allen & Hurricane Mountain Band.
2026 Entertainment Lineup
Please note that we do not permit alcohol, weapons or dogs on the fairgrounds. Our staff kindly appreciate your acknowledgment. We look forward to seeing you at the fair!
