October 2026 Fairs & Festivals in Connecticut
7 events happening across the state in October 2026.
AgriculturalFamilySeasonal
Harwinton Fair
An early-October Litchfield Hills fair — woodsmen shows, antique tractors, and a midway.
Fri–Sun, Oct 2–4Harwinton
AgriculturalFamilySeasonal
Portland Agricultural Fair
A River Valley October fair — livestock, tractor pulls, and farm competitions.
Fri–Sun, Oct 2–4Portland
FreeFood FestivalFamilySeasonal
Southington Apple Harvest Festival
A two-weekend town-green festival — apple fritters, a carnival, a parade, and fireworks.
Oct 2–11Southington
Food FestivalFamily
Chowdafest
A New England chowder cook-off — taste, vote, and crown the best chowder for charity.
Sun, Oct 4Westport
AgriculturalFamilySeasonal
Riverton Fair
The season-ending October country fair — oxen draws, woodsmen events, and home cooking.
Fri–Sun, Oct 9–11Riverton
Food FestivalAgriculturalFamily
Connecticut Garlic & Harvest Festival
A garlic-lover’s harvest festival in Bethlehem — garlic food, seed garlic, and cooking demos.
Sat–Sun, Oct 10–11Bethlehem
FreeFood FestivalMusicFamily
Glastonbury Apple Harvest & Music Festival
A riverside fall festival — apple treats, a carnival, craft vendors, and live music.
Fri–Sun, Oct 16–18Glastonbury