October in Connecticut is undefeated. If you want to make the most of the season, here are 10 incredible fall festivals to put on your calendar this month—including 5 right here in Fairfield County and 5 that are absolutely worth the drive.
Whether you are looking for harborfront celebrations, glowing nighttime lanterns, pumpkin patches, or a deep dive into gourmet garlic foods, autumn in New England offers endless ways to get outside and enjoy the crisp air.
Part 1: Right Here in Fairfield County
Norwalk NICE Festival (Oyster Shell Park)
When: Saturday, October 3 from 12 PM – 9 PM
The Vibe: A vibrant local celebration right on the Norwalk harbor bringing together global music, dance, local food trucks, and artisan crafts to celebrate community diversity as autumn arrives.
New Canaan Nature Center Fall Fair & Cider Saturday
When: Friday, October 9 (5 PM – 9 PM), Saturday, October 10 (10 AM – 6 PM), and Sunday, October 11 (12 PM – 5 PM)
The Vibe: A classic local tradition featuring seasonal crafts, children's activities, and fresh cider right on the wooded grounds of the nature center.
Tokeneke Pumpkin Carnival (Darien)
When: Saturday, October 17 from 10 AM – 4 PM
The Vibe: Running for over 50 years at Tokeneke Elementary School, this is a beloved shoreline tradition that transforms the school grounds into a Halloween-themed carnival and amusement park for local families.
Wilton Scarecrow Fest & Pumpkin Parade
When: Scarecrows on display October 16 – October 31, with the parade on Saturday, October 24 from 2 PM – 4 PM
The Vibe: Wilton Center comes alive with quirky, community-crafted scarecrows lining the streets, capped off by a festive family-friendly afternoon parade.
Beardsley Zoo's Glow Wild Lantern Festival (Bridgeport)
When: Thursdays through Sundays, 5:30 PM – 9:30 PM all through October
The Vibe: A magical nighttime fall event where Connecticut's only zoo lights up with massive, glowing handcrafted animal lanterns.
Part 2: Worth Driving a Bit Farther
Bishop’s Orchards Fall Festival (Guilford)
When: Open daily through November 1, from 10 AM – 5 PM
The Vibe: Located right on the Sound, this quintessential shoreline orchard features massive corn mazes, wagon rides, pick-your-own apples and pumpkins, and a Cider Hut & Garden.
CT Renaissance Faire (Lebanon)
When: Every Saturday and Sunday (plus Columbus Day Monday) from 10:30 AM – 6 PM through October 25
The Vibe: Step back in time with jousting, artisan marketplaces, turkey legs, theatrical performances, and medieval pageantry.
Southington Apple Harvest Festival
When: Running October 2–4 and October 9–11
The Vibe: One of New England's largest and most beloved fall traditions, drawing huge crowds for apple-themed treats, carnival rides, a massive parade, and fireworks.
Connecticut Garlic & Harvest Festival (Bethlehem)
When: October 10–11 (Saturday 9 AM – 6 PM, Sunday 9 AM – 5 PM) at the Bethlehem Fairgrounds
The Vibe: A must-visit for food lovers celebrating all things garlic—from roasted garlic sausage and wood-fired garlic pizza to garlic ice cream, cooking demos, and local agricultural vendors. (Fair warning: You definitely have to try the food here at least once!)
Glastonbury Apple Harvest and Music Festival
When: October 16–18
The Vibe: A massive celebration along the Connecticut River featuring an extensive midway with amusement rides, a 5K road race, local food trucks, craft beer tents, and stellar live music performances all weekend long.
Plan Your Next Move
Whether you are exploring local towns for a weekend outing or thinking about making Fairfield County your permanent home, there is nothing quite like autumn in Connecticut.
If your family keeps having the conversation about relocating to the area, I'm happy to help. Reach out today so we can chat about your goals!
📞 Joe Balestriere, Realtor®
📲 Call/Text: 203-216-0670
📧 [email protected]
💻 seenthensold.com
