St. Peter’s Annual Apple Festival - Monroe, CT - Sep 7 to Sep 8, 2019
Held annually on the first weekend after Labor Day. Lots of apple products including hot apple crisp and apple pies, craft vendors, kids games and more. Free admission and parking.
Oktoberfest of Peekskill - Putnam Valley, NY - Sep 14 to Sep 15, 2019
Get your polka on with great music, great German food and beer, and entertainment
Newtown Arts Festival - Newtown, CT - Sep 21 to Sep 22, 2019
Outdoor festival at Fairfield Hills. Juried artisans exhibit, live music, improv night, food and more.
Kent Fall Festival - Kent, CT - Sep 27 to Sep 29, 2019
The Connecticut Antique Machinery Association’s fall festival on the CAMA museum grounds. Check out working farm equipment, a blackmisth shop, sawmill, exhibits, vendors and more
Ridgefield’s Annual Giant Pumpkin Weigh Off - Ridgefield, CT - Sep 29 to Sep 29, 2019
Giant pumpkin and squash growers from all over the region will compete for cash prizes, plus kids crafts & activities, pumpkin decorating contest, live music, exhibitors, farm stands, baked goods, food trucks, and more! Held at Ballard Park