St. Peter’s Annual Apple Festival - Monroe, CT - Sep 11 to Sep 12, 2021
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 11 to Sep 12, 2021
Get your polka on with great music, great German food and beer, and entertainment
Newtown Arts Festival - Newtown, CT - Sep 17 to Sep 19, 2021
Outdoor festival at Fairfield Hills. Juried artisans exhibit, live music, improv night, food and more.
Kent Fall Festival - Kent, CT - Sep 24 to Sep 26, 2021
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
Harbor Brew Fest - Bridgeport, CT - Sep 25 to Sep 25, 2021
The annual Harbor Brew Fest at the Ballpark at Harbor Yard. The event will tap off with a limited attendance Brewer’s Special from 12pm – 1pm and General Admission will begin at 1pm and will pour until 5pm. An unforgettable day of beer tasting, a beer tasting glass, great music from talented local bands, delicious food from CT’s favorite food trucks and a fun-filled day to enjoy with friends. Brewer’s Special will also grant Exclusive Access to the Brewer’s Beer Garden where limited release and hard to find beers will be served for tasting.
Ridgefield’s Annual Giant Pumpkin Weigh Off - Ridgefield, CT - Sep 26 to Sep 26, 2021
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
New Pond Farm Harvest Festival - West Redding, CT - Oct 16 to Oct 16, 2021
Historical demonstrations, livestock, crafts, food and more!