2019 Fall Festivals

With summer coming to an end and the temperature dropping, it's the perfect time to attend a festival! These festivals are the perfect way to entertain the family with food trucks, live music, activities, and more! 



August 22

Woodstock 2019

Celebrate the 50th anniversary of Woodstock on August 22nd at 7pm at the Penfield Pavillion. Some of the featured music includes Richie Havens, Melanie, The Who, Canned Heat, Ten Years After, Janis Joplin, Santana, Grateful Dead, and more. This is a BYOB event and tickets are $35. 


August 23 - 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 24

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 24 - August 25

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 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 27

Pat Benetar & Neil Giraldo

Live from the Levitt Pavilion, Pat Benetar & Neil Giraldo are bringing their 40th anniversary tour on August 27th. The duo are hitting the road with their band to celebrate 40 years of musical excellence.


August 29

Summer Comedy Series

Fairfield Parks & Recreation and Fairfield Comedy Club present Live Comedy at Penfield Pavillion. Upcoming shows include Mike Britt on August 29th. This is a BYOB event and tickets are $25.


August 30 - September 2 

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.



August 31-September 1

Blues and Views Festival

GETDOWN - CHOWDOWN! Join us for the 12th year of this smokin' hot festival in downtown Westport CT!! LEVITT LIVE! LEVITT LIVE ticket holders have TOTAL ACCESS to the Levitt Pavilion for the Performing Arts for the full line up of incredible performers PLUS access to all the family fun of JESUP JAM!! Kids 12 and under FREE!


August 31 to September 1

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 6 - 8

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

2019 Indian Summer Children's Festival to benefit The Willow Project

The 3nd 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!


September 12

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 15

Latin Music Festival

Kick off Hispanic Heritage Month with music, food, and dancing in Stratford! 


September 21

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 21

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 21

The Connecticut Ukulele Festival

The Connecticut Ukulele Festival is pleased to announce Bruce Off Broadway, a Ukulele Tribute to the music of Bruce Springsteen, as the headline act for the September 21 event. The concert will cap a full day of ukulele and music, food and drink, workshops, strum-a-longs, free performances and an open mic competition. It all starts at 9:00 a.m. at the Pequot Library in Southport, CT. www.ctukulelefestival.com for details.


October 5

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 12-15

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 19

The Great Pumpkin Festival

The Great Pumpkin Festival is a fun, annual family event held each year at Boothe Memorial Park. As in the past years, the festival will feature an adjudicated pumpkin carving contest. 


October 19


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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13 Aug 2019

By Haley Falls