2018 Fall Festivals

When it comes to summer in Connecticut, we often think about heading to the beach, exploring new seafood restaurants, and going to backyard cookouts. But have you thought about all the unique festivals happening in Fairfield County and the rest of the state? Here’s a complete guide to festivals throughout the summer!




August 24 - 26

Plainville Hot Air Balloon Festival

The annual Plainville Hot Air Balloon Festival, presented by the Plainville fire company, attracts thousands of spectators to what organizers consider one of the biggest and last remaining balloon festivals in the Northeast. There is also a car show, fireworks, a sock hop, and local food vendors, so bring the whole family!


August 25 

Art in the Park Festival and Art Contest 

Weir Farm National Historic Site, Friends of Weir Farm, the Weir Farm Art Center, and G&B Cultural Center will host the park's second annual Art in the Park Festival in Wilton. Artists are encouraged to bring their supplies, and the park will provide supplies for those that don't have their own. All visitors will have the opportunity to create works of art and enter the contest. 


August 25

New London Food Truck Festival

Choose your favorite food truck, grab an order, and enjoy live music at City Pier stage with  DJ Frank Lo at the Custom House pier! The event is 6:00 PM – 9:00 PM. FREE kids activities include face painting and balloon animals.


August 25 - August 26

Hey Stamford! Food Festival

The Hey Stamford! Food Festival will feature the area's most delicious food trucks, restaurants, talented chefs and breweries that embody the scene in and around Stamford, CT. This two-day, family-oriented event will highlight over 40 local food trucks and restaurants, dishing out fresh, mouthwatering local bites. Highlights also include the finest in regional and national breweries!


August 31 - September 3 

Orange Odyssey Greek Festival 2018 

Enjoy classic Greek cuisine, Greek cooking demonstrations, a Greek marketplace, a giant tag sale, presentations on Greek culture and religion, along with tours of Saint Barbara Church. Greek dance performances and lessons will also be available as well as a kids area with rides, games, magic shows, and raffles.



September 1 - 2

Blue Views & BBQ Festival 

The Westport - Weston Chamber of Commerce and DBD Productions will be hosting the 2018 Blues, Views & BBQ Festival, with a Labor Day weekend lineup that includes headliners Karl Denson's Tiny Universe, Fantastic Negrito, Sister Sparrow and the Dirty Birds, Carolyn Wonderland and more! There will be soulful, southern inspired food, music and family fun to the banks of the Saugatuck River in beautiful downtown Westport. A weekend experience that never disappoints sell out crowds, this signature end of summer event is set to deliver another stand out year.


September 1 - 2 

New England Food Truck Festival at Mohegan Sun 

The New England Food Truck Festival returns for a third year at Mohegan Sun! This festival will feature dozens of food trucks, live music, entertainment for kids, face painting, field games and much more.  A truly unique event where you can linger until you have sampled all the best of what we have offer!


September 5 - 9 

CT Martime Heritage Festival 

The Connecticut Maritime Heritage Festival is a five day annual celebration promoting the State of Connecticut’s maritime heritage and spirit of innovation in conjunction with Connecticut Maritime Heritage Week. Experience unique tours aboard a fleet of boats including U.S. Navy and U.S. Coast Guard ships, merchant marine vessels, and historic schooners. Festival highlights also include a U.S. Coast Guard search & rescue demonstration, music at the Fort Main stage concert, a "Swingin’ on the Pier" dance party, a “Meet the Crew” party, a parade of ships, The Morgan Cup Yacht Race, a Maritime Career Opportunity Expo, a burning of Benedict Arnold by costumed reenactors, a children’s fishing tournament, and the 6th annual "Chowder Challenge.”


September 7 - 9

Norwalk Oyster Festival

Get ready for food, vendors, entertainment, and a celebration of the history of the oyster industry based in Norwalk! The annual Norwalk Oyster Festival will be held in Veteran’s Park, Fort Point Street and Seaview Avenue, East Norwalk. Funds raised from the festival allow the Seaport Association to continue its educational programs, stewardship for the 1868 Sheffield Island Lighthouse, Norwalk Islands habitat restoration projects with the U.S. Fish & Wildlife Service and other services. 


September 8 - 9

Trumbull Fall Fest 

This family-friendly annual festival presented by the Town of Trumbull features midway rides for all ages, live music, carnival games, favorite fair food, food trucks and Saturday night fireworks. Festival food options include barbecue, tacos, seafood, falafel, Italian dishes, ice cream and more, as well as traditional fair fare and a craft beer and wine tent.


September 9

Fairfield Flavor Wine Festival

The Warehouse at the Fairfield Theater Company will be transformed into a local winery before your very eyes! Try champagne, rosé, sparkling wine, and red and white wines all from the best distributors. Each ticket purchased will include unlimited wine, a sampling glass, and local craft foods. Live music will also play throughout the evening.


September 15

Westport LobsterFest 

Westport Rotary Club's LobsterFest is the beach event of the season, a fun gathering for the whole family where all of the profits go to support non-profit work at home and abroad. Adults have the choice of two 1.25 lb lobsters or a 14 oz steak, both with all the trimmings, plus unlimited wine and beer. There’s also a kid's menu, for 12 and under, and a raw oyster and clam bar. Live music and kids games round out this festive way to celebrate summer’s end by scenic Long Island Sound.


September 22

Norwalk St. Philip's Annual Family Fall Festival

After two successful years, the St. Philip Family Fall Festival in Norwalk returns with more local vendors for fantastic shopping, children’s programs for lots of family fun and a hot grill for delicious food. There will also be music, crafters, and raffles. he 2017 Festival
attendees heard great music, shopped with many crafters and ate delicious food. The Family Fall Festival brings together activities for all ages!


September 29 

Westport Autumn Bounty Festival 

Welcome the season of crisp air, fresh apples, and colorful leaves at our annual Autumn Bounty Festival! There will be a huge celebration with live music, crackling fires, and lots of local friends and artisans from Phoencia Flea.


September 29

Connecticut Ukulele Festival

Brought to you by Steve Forlano and Peter Propp, the first annual CT Ukulele Festival will take place at Factory Underground in Norwalk. There will be workshops, open mics and group strums. There will also be a ukulele concert featuring the CUkes (finalist in CT's Got Talen) and a National Touring Act. Doors open at 12pm for the workshops and 6:30pm for the concert. Don't miss out on this first-ever event! 


September 30

2018 Indian Summer Children's Festival to benefit The Willow Project

The 2nd annual childrens' festival is a fun, family friendly event at Audubon Greenwich to benefit The Willow Project. There will be live music on the lawn, food vendors, raffles and all of Lynn's favorite activities and handicrafts - painting, tie-dye, hip hop dancing, yoga, candy bar, scavenger hunt and much more! Tickets $25 per person in advance, $30 day of event. Children 3 & under FREE!


October 6 

Groton Fall Festival 

Head to the Poquonnock Plains Park in Groton for a fun-packed day for the whole family! This year's event will be better than ever, with traditional fall activities, family tournament games and prizes from local businesses, food and beverage, artists, artisans and crafters, and over 100 local vendors and businesses from around the Groton and Mystic regions.


October 6

Chowder Days Festival

With cool fall days comes the desire to indulge in a hot bowl of chowder – and what better place to do so than Mystic Seaport? Coastal Gourmet’s Chowder Days menu is sure to satisfy all appetites and features a variety of chowders and bisques, along with clam fritters and other fall favorites. 


October 13


New to downtown Westport, Westoberfest will feature a wide array of regional breweries, the Westport Library Lit Fest, air-cooled cars, delicious food from local restaurants, live entertainment, and fun family activities, all on the sidewalks of downtown. 





Do you know of any festivals around Fairfield County that you'd like to see on this list? Let us know on Facebook or Instagram at @ourtowncrier. 


1 Review
Fairfield, CT
Great variety

Great variety of festivals around Fairfield County - music, cultural, food, etc. Love it!

July 2018

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18 Sep 2018

By Haley Falls