Family events in Fairfield, CT

The Second Chance makes its debut at the Durham Fair, delivering a lively mix of traditional music and Irish pub favorites. The performance features special guest Irish vocalist Don Kane.

RGB takes the headlining slot on the Green Stage at the 106th Durham Fair in Durham, CT. The group features Rob Glassman, Mike Piercey, Ralph Santoro, and Eli Farland. Sound engineering for the evening will be handled by Aaron Stone.

The Downtown Milford Farmers Market fills Wasson Field with the tastes and colors of the season, offering autumn produce alongside locally raised meats, dairy, baked treats, and other farm goods perfect for family meals and seasonal cooking. Shoppers can explore a wide mix of vendors featuring fresh fruits and vegetables plus flowers, sustainable apparel, baby essentials, home décor, pet products, and artwork. Food trucks and specialty makers serve breakfast and brunch choices, coffee and matcha, ice cream, smoothies, gluten-free baked goods, barbecue, and other seasonal bites. Live music from local performers adds an easygoing soundtrack while you browse. Activities often include pet adoptions, cooking demonstrations, and visits from agriculture experts. Families will find a dedicated Children’s Market and the Piglets Club, with story time, farm animal visits, face painting, and chances for enrolled kids to earn $1 tokens to pick out their own fruits and vegetables while learning about farming. Participating farmers accept SNAP, WIC, and senior vouchers to help make fresh, local food more accessible. The market places children at the heart of its mission, nurturing early connections to healthy eating and community. The Downtown Milford Business Association partners with The Giggling Pig of Milford to bring the Piglets Club to life.

Discover a welcoming community market at the First Congregational Church of Norwalk. Browse farm fresh fruits and vegetables, artisanal breads, coffee from local roasters, and distinctive goods created by area farmers, bakers, and makers. It is a convenient place to stock up on weekly groceries, support small businesses, and enjoy a relaxed morning outdoors. Meet neighbors, chat with vendors, and take home seasonal finds.

The 39th annual Bigelow Tea Community Challenge brings a mix of fitness and family friendly activities to the Wakeman Boys & Girls Club in Southport, CT, rain or shine. In person participants can choose from a certified 5K run that passes the harbor and historic Southport area, a noncompetitive 3K walk for individuals, friends, and families of all ages, and a kids fun run featuring a 100 yard dash and a 1 mile jog with awards, snacks, and plenty of activities for children from pre K through sixth grade. Complimentary T shirts and goody bags are part of the experience, along with activities, food, and beer for those with valid ID. Virtual participation options are available for anyone unable to attend in person. The event welcomes runners and walkers to enjoy views of Southport Harbor and the historic district while supporting local nonprofit organizations. Participants are encouraged to share training and day of moments on social media with the hashtag #BTCC.

Returning to Sasco Beach for another season, this event pairs sunset views with wood-fired pizza, s'mores, and bombolonis. Weekly specials rotate, and Margherita Monday giveaways take place each week.

At Stamford Recreation Star Center, this lively Spanish music class invites children ages 1 to 4 to learn through songs, movement, rhythm games, and hands-on activities. Led by Armelle For Kids, the session blends play and language so new vocabulary is absorbed naturally while everyone stays active and engaged. Caregivers can share the experience alongside their little ones, adding to the friendly, interactive atmosphere. The program is offered as a ten week series at a cost of $219 per child.