Fall Fairs & Festivals 2026

North Haven Fair, North Haven
September 10-13, 2026
www.northhaven-fair.com

East Haven Fall Festival
September 11-13, 2026
www.ehfallfestival.com/

New Haven Cocktail Week
September 13-19, 2026
www.newhavencocktailweek.com

The Guilford Fair
September 18-20, 2026
www.guilfordfair.org

Closer to Free Ride
September 19, 2026
www.rideclosertofree.org

New Haven Grand Prix & Apizza Feast
September 25, 2026
www.newhavengp.com

The Durham Fair
September 24-27, 2026
durhamfair.com

CT Folk Fest & Green Expo
September 26, 2026
www.ctfolk.org

Orange Country Fair
September 19 & 20, 2027
www.orangectfair.com

Celebrate Wallingford
October 3-4, 2026
wallingfordcenterinc.com

New Haven Chalk Art Festival
October 3, 2026
theshopsatyale.com

New Haven Dragon Boat Festival
October 3, 2026
www.canaldock.org

Downtown Milford Business Association Annual Wine Trail
October 10, 2026
downtownmilfordct.com

Fall Festival at The Big Red Barn
Open daily through November 1
bishopsorchards.com

New Haven Restaurant Week
November 1-14, 2026
Website