Family events in Middletown, CT

Movies in the Plaza returns to downtown New Haven with complimentary Wednesday night film screenings from May through October at Pitkin Plaza. Settle in with a blanket or lawn chair and enjoy an evening under the stars featuring a mix of blockbuster favorites, nostalgic throwbacks, cult classics, and selections suitable for all ages. Admission is free, with registration completed at the check-in table upon arrival, and light snacks are provided at no cost. Attendees are encouraged to bring their own seating, as bistro and lawn chairs are available in limited numbers. Screenings are weather dependent, with updates shared on the day of the event. Viewer discretion is advised, so please review each title’s themes and content before attending with younger audiences.

A weekly Pokémon league night welcomes all ages with tournaments and open trading throughout. Three formats are available, including Standard, Gym Leader, and Ditto. Entry fees start at $5 and vary by event. Players should have a Pokémon Player ID, and staff at the shop can assist with the sign-up process if needed.

Enjoy a weekly Pokémon League night held every Thursday with constructed format play. All ages are welcome, and trading is always allowed. Bring a deck and play friendly matches with the local community. For questions, call (203) 833-1535 or email reyes@eejlworldllc.com. When using the store locator to find the Riftbound event, search for E.E.J.L. with the periods included.

The Portland Agricultural Fair returns for a third year at the grounds, hosted by Chris Cote and the Portland Fish and Game Club. Additional details will be shared as they become available.

Makers of the Realm transforms the Bozrah Farmers Market into a Renaissance-inspired celebration of fantasy and craftsmanship. Artisans, crafters, and makers fill the market with handmade treasures, from pottery and artisan jewelry to leather goods, carved wood, hand-poured candles, textiles, and original artwork, along with other one-of-a-kind pieces suited to a castle or a cottage. The market’s farm roots shine through with fresh produce and other local products, plus plenty to enjoy, including savory foods and sweet treats. Live music adds to the family-friendly atmosphere, and costumes are welcome for vendors and visitors, though not required. Guests can browse the wares, sample delicious offerings, and celebrate the imagination and skill of makers in the community throughout the evening.

The 9th annual New Haven Dragon Boat Festival brings paddling excitement and friendly competition to the water. Community teams can register to participate, coming together for teamwork and a lively, fun experience.

Settle into a cozy setting and spend time with a lively herd of young goats that love to romp, nibble, and cuddle. An on-site event leader will guide the experience, introducing participants to the herd and helping match each guest with especially snuggly companions. These affectionate animals may even hop into a lap for extra cuddle time. It is a gentle opportunity to unplug, breathe in fresh air, and enjoy the moment. Bringing a blanket is recommended to make close-up time even more comfortable. There is ample time to relax, socialize, and capture memorable photos or a selfie with these furry friends.

BB and another person will be at the Bristol Farmer’s Market on select dates throughout the season, with multiple appearances scheduled.

This family-friendly gathering in New Haven features arcade games and tasty food. Children must be accompanied by a parent or legal guardian. Barcade donates a portion of Family Day token sales to Gamers Outreach, a charity that provides recreation to children in hospitals through video games and the gaming community.

Enjoy unhurried moments at the fence feeding and meeting a gentle herd of goats. The pace is up to each visitor, which makes this a welcoming option for toddlers, young children, and anyone who prefers connecting with animals without hurry. A friendly, knowledgeable event leader will be nearby to answer questions and share interesting tidbits. Guests can relax, take in the lake scenery, and savor a peaceful pause on the farm. This easygoing, flexible visit is intended for all ages and abilities, offering a sweet way to get to know the goats without a formal structure.

Elizabeth Park hosts the return of this annual production, unveiling a new show and a refreshed vibe for 2026. Alongside the performance, the plan includes a park cleanup, engaging activities, and hands on art projects, with more information to come.

Move with MADD Connecticut takes place on the East Haven Town Green and honors the life of Mason Fish, who died from injuries sustained in an impaired driving crash in 2023. The event includes an opening ceremony and a kickoff on the green. In partnership with The Shore Line Trolley Museum, participants walk from the green to the museum for a trolley ride.

Returning for its second year, this Haunted Hayride offers a night of hair-raising fun and eerie adventures. Tickets are on sale, and the organizers are seeking volunteers, participants for live scenes, and sponsors to help bring the experience to life.

Experience a weekly Connecticut car show sponsored by the Farmer's Cow Calfe, showcasing classic, muscle, and street cars. Enjoy good food, explore a variety of standout vehicles, and take part in a family-friendly outing suitable for all ages.

The Plainville Fire Company is hosting a fall pasta supper. Admission is $12 per person, with a $10 rate for senior citizens. The meal includes bread, salad, pasta with meatballs, beverages, and cake. Children under 7 eat free.

Cosmic Bowling at Kickback n Bowl assigns lanes in the order guests arrive. If your group has more than six people, calling ahead is encouraged so an effort can be made to keep lanes together.

Nightshift returns for a third appearance at Celebrate Wallingford, a two-day festival that highlights Taste of Wallingford, where attendees can sample dishes from local restaurants. The celebration features live entertainment, arts and crafts shows, and activities for children. Visitors can enjoy a wide variety of food while taking in familiar hits from the 60s, 70s, and 80s.

A festive parade celebrating the apple harvest as part of the 2026 festival.

At Capital Ice Cream, homeschool families will find a welcoming meetup that offers a place for children to play and for caregivers to connect. The emphasis is on learning through friendship, imagination, and playful exploration. Families may bring lunch while children enjoy hands-on activity stations, storytime, and both solo and collaborative play. There is also time to meet other homeschoolers and plan future play dates. Participants can make a short visit or stay longer, whatever fits the day.