Some of Connecticut's best October traditions are a short drive from home, and a few are worth a full Saturday road trip. We sorted this year's harvest and pumpkin festivals into two groups: the ones in and around Fairfield County, and the ones worth the drive.

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Close to home

New Canaan Nature Center Fall Fair, Oct. 9–11. A Fairfield County classic for families, with pumpkins, mazes, carnival rides, apple-themed games, live music and food.

Fairfield Harvest Market, Sat., Oct. 17, Old Town Hall Green, Fairfield. Shop local makers and vendors, with live music and food, right in the heart of town.

Great Pumpkin Festival, Sat., Oct. 17, Boothe Memorial Park, Stratford. Pumpkin displays, crafts, kids' activities, food and seasonal entertainment on the grounds of one of Stratford's most historic parks.

Pumpkins & Planets Fall Fest, Sundays, Oct. 18 & 25, 10 a.m.–2 p.m., Stamford Museum & Nature Center. A family fall festival that pairs pumpkins and seasonal activities with space-themed fun.

Harvest Fest, Sat., Oct. 24, 1–4 p.m., Reservoir Community Farm, Bridgeport. An afternoon at Bridgeport's urban farm, with fresh food, live music, local vendors and community activities.

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Worth the drive

Southington Apple Harvest Festival, Oct. 2–4 & 9–11, Southington Town Green. One of the largest fall festivals in New England, now in its 57th year. Admission is free, and there are carnival rides, live entertainment, crafts, contests and the famous apple fritters. The parade steps off Sunday, Oct. 4, at 2 p.m.

Connecticut Garlic & Harvest Festival, Oct. 10–11, Bethlehem Fairgrounds. Garlic in every form you can imagine, plus cooking demos, live music, growing lectures, crafts and specialty foods. Admission is $10 for adults and $1 for kids under 12, cash only.

Riverton Fair, Oct. 9–11, Riverton. Often called the last country fair of the season, and running since 1909. Expect rides, farm animals, food, live music, exhibits and baking competitions in the Litchfield Hills.

Glastonbury Apple Harvest & Music Festival, Oct. 16–18, Riverfront Park, Glastonbury. More than 50 musical acts, a full carnival, over 100 craft vendors, seasonal food and a children's activity zone.

Pumpkin Fest, Sat., Oct. 17, YMCA Camp Mohawk, Litchfield. A family day at camp, with pumpkin painting, boating, archery, s'mores and hot cider by the pond.

Great Pumpkin Festival, Sat., Oct. 17, Downtown Putnam. Vendors, live performances, kids' activities, crafts, seasonal dining and Connecticut's official giant pumpkins.

Mystic Apple Festival, Oct. 17–18, Olde Mistick Village, Mystic. Free to attend, with local artisans, fall foods, live entertainment, and apple, pumpkin, maple and caramel treats.

Ivoryton Village Pumpkin Festival, Sat., Oct. 24, Ivoryton (Essex). A costume parade kicks off at 4:30 p.m., followed by pumpkin carving, trunk-or-treating, music, treats and an illuminated jack-o'-lantern display.

Pumpkintown U.S.A., through Oct. 31, East Hampton. A non-scary fall destination filled with pumpkinhead characters and seasonal displays, perfect for younger kids.

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Planning your weekends

• Oct. 2–4: Southington Apple Harvest Festival (weekend one)
• Oct. 9–11: Southington (weekend two), New Canaan Nature Center Fall Fair, Riverton Fair and the Garlic & Harvest Festival (Oct. 10–11)
• Oct. 16–18: Glastonbury, Mystic, Putnam, Camp Mohawk, Stratford's Great Pumpkin Festival and the Fairfield Harvest Market, plus Pumpkins & Planets on Sunday
• Oct. 24–25: Harvest Fest in Bridgeport, Ivoryton's Pumpkin Festival and Pumpkins & Planets on Sunday

Festival dates, hours and rain dates can change, so check with the organizer before you go.

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More fall guides from our team

• Apple Picking & Pumpkin Patches Near Fairfield County
• Haunted Houses in Connecticut: What's Right for Your Kids
• Halloween 2026 in Fairfield County, Town by Town
• Oktoberfest & Fall Food Events in Fairfield County and Beyond

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