Fall Festivals in Fairfield County, CT (2026)

Westport Library · Westport

Drop by the Children's Library anytime during the day to pick up everything you need for a fun craft to make at home! Kids (5-12) September 4: Paper Animal Puppets October 2: Pumpkin Yarn Craft

Earthplace · Westport

A full day of family activities at Earthplace including a corn pool, arts & crafts, pumpkin bowling, nature exploration, rotten log hotel, tree weave, eagle's nest and animal encounters. Food trucks and a raffle are…

Hop & Vine Taproom · Stamford

Hop & Vine Taproom's second annual Oktoberfest block party, starting at noon. $20 gets a limited-edition 32 oz HVT signature stein filled with the beer of your choice (last year's steins sold out in the first hour).

Darien Commons · Darien

Free family-friendly event featuring fall crafts, photo ops, kids activities, a petting farm, and food samples from Sweetgreen, Naya, Chip City and Van Leeuwen. There is a beer and wine garden for adults. Activities…

Nod Hill Brewery · Ridgefield

The biergarten hosts a free performance of traditional German brass music, oompah tunes, and drinking songs. Seating is available on a first come, first served basis, and no tickets, reservations, or advance notice are…

Third Place by Half Full Brewery · Stamford

Final Oktoberfest day with a hammerschlagen contest 2-5pm and the annual steinholding competition at 3pm ($15 entry includes 1L of beer).

The Gardener's Center · Darien

The Darien Chamber of Commerce's adults-only Oktoberfest at The Gardener's Center: live music, German-inspired food and drinks, themed games and a silent auction; traditional attire optional. General public $125…

Mill River Park Collaborative · Stamford

For eight weeks this fall, join us on Sundays as toddlers and their caregivers discover a different story together, each one capturing the seasonal spirit of autumn.

Newsylum Brewing Co. · Newtown

SUN OCT 4TH- NEWSYLUM OKTOBERFEST 2!!- 12:00PM-6:00PM

Newsylum Brewing Co. · Newtown

Sun Oct 4th- The Oktoberfest Band!- 1pm- 2pm Sun Oct 4th- C-Sides- 2:30pm-5pm

Ridgefield CT Republican Town Committee · Ridgefield

Annual Oktoberfest fundraiser with traditional German food including bratwurst and pretzels, local beer and wine, and live traditional music. The farm has animals and yard games including corn-hole. Family-friendly and…

Catherine Violet Hubbard Animal Sanctuary · Newtown

Outdoor storytime about fall leaves for children 1-5 with a caregiver.

Stew Leonard's · Norwalk

Those who purchase a pumpkin at Stew's in Norwalk on October 10th, 11th & 12th between 11:00AM and 5:00PM are invited to a complimentary pumpkin painting event outdoors in the Garden shop. No advance registration…

Stamford Town Center · Stamford

Family-friendly fall festival with Explorando con Hijos: games, music, food, performances, vendors and more. Free entry for all ages.

Newtown Community Center · Newtown

Visit our pumpkin patch to select a pumpkin, then paint it with your choice of character or design. Wear your costume and spend the afternoon creating while enjoying Halloween-themed activities and entertainment.

Pinot's Palette · Stamford

Painted Pumpkins. Join the paint and sip party at this Stamford, CT studio.

Atria Darien · Darien

Fall Car Show Oktoberfest at Atria Darien: lots of classic cars, food and drink, and entertainment. Free admission.

Wilton Chamber of Commerce · Wilton

The Wilton Chamber of Commerce is pleased to announce the return of the highly anticipated annual Scarecrow Fest to Wilton Center this fall. Supported by community partner, ASML and in collaboration with the Wilton…

Museum of Darien · Darien

Evening of colonial tavern fun with a bonfire, beer and bites at the museum.

First Congregational Church of Bethel · Bethel

Games, crafts, storytelling, pumpkin painting and autumn treats for families.

Wilton Historical Society · Wilton

The 6th Annual Great Wilton Pumpkin Fest will return to the Wilton Historical Society on Saturday, October 17th from 1 pm to 3 pm. It’s fun for all ages with all things pumpkin! Join knowledgeable docents in open…

Stamford Museum & Nature Center · Stamford

Early Bird Tickets NOW on sale for both Fest dates! Family Premium & Family Plus Members: Enter Discount Code FREEFALLFEST at checkout to receive your free fest day.

Redding Grange #15 · Redding

The 5th Annual Redding Grange Fair brings together local farmers, crafters, and home producers to exhibit their work. Entries include poultry, seasonal flower arrangements, baked goods, maple syrup, needlework…