2026 Summer Fairs and Festivals in & Around Fairfield County

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A family at a summer fair.As soon as Memorial Day comes around, so does my favorite time of year! Not only is it the end of the school year, the start of the summer season, and when everyone’s mood starts to shift for the better, but it is also time for summer fairs and festivals! My children wait all year for the first time they can fly high on a ride, win a goldfish, or bite into something sweet (I prefer the savory side of things)! I can already smell the cotton candy and freshly popped kettle corn, and I can envision all the bright, twinkling lights.

There will be a lot of fun this summer in Fairfield County. Check out this list of local Fairfield County summer fairs and festivals, and mark them on your calendars! These events are not to be missed!

May 28-31

  • Greek Fair: 1230 Newfield Avenue, Stamford, CT; Thursday 6:00-10:00 p.m., Friday 6:00-11:00 p.m., Saturday 1:00-11:00 p.m., Sunday 1:00-8:00 p.m. In Stamford, this fair has been lovingly known as the “official” start to summer.

June 10-13

  • St. Rose Church Fair: St. Rose Church, Newtown, CT; Wednesday to Saturday, 6:00-10:30 p.m. This is an earlier weekend for this fair, so mark the change!

June 12-15

  • Westport Woman’s Club: 44 Imperial Avenue, Westport, CT; Thursday 6:00-10:00 p.m., Friday 6:00-10:00 p.m., Saturday 1:00-10:00 p.m., Sunday 1:00-5:00 p.m. The fair proceeds go to the Westport Woman’s Club and to the yearly grants and scholarships it awards to local recipients.

June 26-27

  • Trumbull Day: A fun-filled family event with food, vendors, carnival rides and games, children’s entertainment, and a main stage featuring local bands and fireworks. Located at Hillcrest Middle School, Trumbull. Friday 6:30-10:30 p.m., Saturday 2:00 p.m.-10:30 p.m.

July 11-15

  • St. Catherine Siena Carnival of Fun: St. Catherine’s Church, Riverside, CT; Wednesday to Saturday, 6:00-11:00 p.m. There will be dining, live entertainment, rides, games of skill and chance, an amazing raffle, and more for all ages!

July 21-25

  • St. Pio of Pietrelcina: (aka Pompeii Church), East Haven, CT; Tuesday to Saturday, 6:00-10:00 p.m. It will be the 68th annual year of this fun festival!

July 28-August 1

  • Easton Fireman’s Carnival: Easton Fire Department, Easton, CT; Tuesday to Saturday, 6:00-11:00 p.m. Carnival games and rides, bingo, great food, and a free shuttle bus for those parking at Helen Keller School. Parking is also available at Silverman’s Farm.

August 12-15

  • St. Roch Church Fair: St. Roch Church, Greenwich, CT; Wednesday and Thursday, 6:00-10:00 p.m., Friday 6:00-11:00 p.m, and Saturday 4:00 p.m.-11:00 p.m. Fun, games, and food! Plus, there is awesome live music!

August 26-29

September 1-5

  • St. Leo Fair: St. Leo Church, Stamford, CT; Tuesday and Wednesday, 6:00-10:00 p.m., Thursday & Friday 6:00 p.m.-11:00 p.m., and Saturday, 2:00-11:00 p.m. Known to locals as the “end of summer” fair. This fair has it all! Raffles, bingo, games, rides, and many delicious food offerings.

September 11-13

  • Norwalk’s Oyster Festival: Friday, 6:00-11:00 p.m., Saturday, 11:00 a.m. – 11:00 p.m., Sunday, 11:00 a.m. – 8:00 p.m. Held at Veteran’s Memorial Park in Norwalk. The Norwalk Seaport Association puts it on to raise funds to support the historic Sheffield Island Lighthouse. This festival has the usual rides, games, and food, but also features one-of-a-kind vendors for that special gift for yourself or someone you care about!

Did we miss any summer fairs or festivals near you? What are some of your favorites?

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