Middletown Family Fun Fest

Middletown Family Fun Fest Returns Sept. 11-12, 2026 Celebrating 54 Years of Small-Town Charm, Big-Time Fun Downtown Middletown and Wetherby Park around City Hall Mark your calendars! The 54th Annual Middletown Family Fun Fest returns to Downtown Middletown and Wetherby Park for two full days of family-friendly fun: Friday, September 4 | 5 PM – 9 PM Saturday, September 5 | 10 AM – 10 PM This free, family-focused celebration remains one of the region's most beloved neighborhood festivals, bringing the community together for live entertainment, hands-on activities, great food, and unforgettable fun for all ages. Main Stage Entertainment Friday, Sept 11. 5-6pm School of Rock 6-7pm Middletown area churches 250th celebration choir. 7pm National Anthem and Smoke on Aviation Flyover 7:15-9pm JD Shelburne Saturday Sept 12 1:30-3pm Atomic Groove Machine 3-430pm Melody Rescue 5-630pm Empty V's 80's band 7-9pm Rockland Road Band 9:30pm SkyZone Drone Show with more than 150 drone

All Ages