June Events
Ice Cream Social @ New Canaan Museum & Historical Society
Sunday, June 1st, 1-3PM
Join us on the great lawn at the Historical Society. There will be an Antique car show, old fashioned games, New Caanan Town Band, children’s activities and of course ice cream!
Healthy Kids Day® at the YMCA of Greenwich!
Sunday, June 1st, 12PM-3PM
From cradle to career, we empower young people to lead inspired, successful lives. Healthy Kids Day® is an annual national event celebrated at Ys across the country to help inspire healthy habits in kids and families. Join us on Sunday, June 1, from 12:00 – 3:00 p.m. at the YMCA of Greenwich for a day of celebrating kids being kids!
Experience:
- Arts & Crafts
- Dancing
- Interactive Games
- Tie Dye Shirts
- Healthy Refreshments
- Raffles & Prizes
and more brought to you by our community partners!
To RSVP and learn more about this FREE event, please visit: greenwichymca.org/events/details/97/Healthy-Kids-Day
2025 Yankee Doodle Fair
Thursday, June 12th-Sunday, June 15th (times vary)
Once again, during Father’s Day Weekend, “kids of all ages” will gather at the Westport Woman’s Club (44 Imperial Avenue, Westport, CT) to partake in one of the town’s oldest and most cherished family events, the Westport Woman’s Club’s YANKEE DOODLE FAIR.
This year’s family Fair kicks off on:
- Thursday, June 12 (6pm – 10pm)
- Friday, June 13 (6pm – 10pm)
- Saturday, June 14 (1pm – 10pm)
- Sunday, June 15 (1pm – 5pm)
The Yankee Doodle Fair will feature carnival rides and games provided by Stewart Amusements. A pay-one-price unlimited ride wristband will be available for all days of the Fair, including Friday and Saturday nights! Our youngest visitors will be excited to see that Sand Art is returning to the Fair this year.
Kids Fest at Lake Compounce
CT Irish Festival & Field Day Weekend
There will be entertainment, children’s activities, competitions, Irish food and beverages, and Gaelic sports.
Midsummer Fantasy Renaissance Faire – CT
June 28th, June 29th and July 4th from 11AM-630PM
Enjoy a fantasy world set in a time long ago where elves, fairies, orcs, goblins, animal-kin, dwarves, and magic are REAL.
Location: 119 Pulaski Highway, Ansonia, CT, 06401
Strawberry Festival at Lyman Orchards
There’s no sweeter way to celebrate the start of Summer ‘25 than by joining in on all the fun at the Lyman Orchards Strawberry Festival! It’s all happening at the Apple Barrel Farm Market and grounds on Saturday, June 14th, 10 am – 4 pm!
The Stratford Main Street Festival- CT
The Main Street Festival is an annual town-wide event celebrating the many organizations, programs, and services the Town of Stratford has to offer, bringing together over 150 local vendors, including entertainment, food trucks, booths, and artists. The event also provides an opportunity for Stratford’s diverse organizations to educate the public about their functions and support fundraising efforts. Vendor booths and trucks will line Main Street, allowing residents to stroll through Stratford Center, embracing the beauty of the town. A DJ and various entertainers will be performing throughout the day.
St. Rose Church Fair
St. Rose Church, Newtown, CT; June 18-22, Tuesday to Saturday, 6-10:30 p.m. Last year was the return of this fair, which proved to be super fun!
Trumbull Day
Trumbull Day is 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. June 27-28, Friday 6:30-10:30 p.m., Saturday 1:30-10:30 p.m.
July Events
JAWSFest at Mystic Seaport Museum
On July 5, “we’re gonna need a bigger boat” to celebrate the 50th anniversary of JAWS! Whether you’re an islander, a tourist, or a local, join us for JAWSFest at Mystic Seaport Museum. Enjoy shark-themed fun for all ages including a shark cage photo op, crafts, and sea shanties. Learn about shark conservation and research from regional experts and kick off Shark Week with live sea music and an outdoor screening of Jaws.
Activities take place all day, 10:00 a.m.–5:00 p.m. An after-hours concert and outdoor movie screening will take place in the evening. General admission will cover both daytime and evening programming.
Raspberry Festival at Lyman Orchards
The Lyman Orchards Raspberry Festival celebrates raspberry season with some fun for the whole family at the Apple Barrel Farm Market on Saturday, July 5th, 10 AM – 4 PM!
Activities:
- 8 AM – 4:30 PM: Pick Your Own Blueberries & Raspberries, located on South Street
- 9 AM – 4 PM: Apple Barrel Deli Open
- 10 AM – 4 PM: Face Painting by Lara
- 10 AM – 4 PM: Visit the Renewal by Andersen table for some giveaways and information about the company!*
- 10 AM – 5:30 PM: Ice Cream Window Open on the Apple Barrel Patio (with a special raspberry themed sundae!)
- 10:30 AM- 11:30 AM – School of Rock*
- 11 AM – 3 PM: Food Trucks
- 1 PM – 4 PM: Live Music from Slewfoot*
*Free activities!
Admission to the Lyman Orchards Raspberry Festival is FREE!
Teddy Bear Festival at Connecticut’s Beardsley Zoo
Bring your favorite teddy bear friend or any special plush pal to the Zoo. This beary fun day will feature children’s activities and storytelling focusing on Bear Awareness and facts about real bears. There’s even a Teddy Bear Clinic where you can get a free health checkup for your friend, sponsored by Yale New Haven Children’s Hospital. Our Teddy Bear Festival is also sponsored by the State of Connecticut on behalf of the CHET 529 College Savings Program. Location: 1875 Noble Avenue, Bridgeport, CT, 06610. Dates: 07/19/2025. Time: 10 am – 2 pm.
St. Catherine Siena Carnival of Fun
St. Catherine’s Church, Riverside, CT; July 10-13th, Wednesday to Saturday, 6-11 p.m. There will be dining, live entertainment, rides, games of skill and chance, an amazing raffle, and more for all ages!
Easton Fireman’s Carnival
Easton Fire Department, Easton, CT; July 30th-August 3rd, Tuesday to Saturday, 6-11 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 + September Events
St. Jude Church Fair
St. Jude Church, Monroe, CT; August 21-24th, Wednesday to Friday, 6-10 p.m., Saturday, 5-10 p.m. Fun and games galore!
St. Leo Fair
St. Leo Church, Stamford, CT; August 27th-31st, Tuesday to Friday, 6-11 p.m., Saturday, 2-11 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.
Norwalk’s Oyster Festival
September 5th-7th, Friday, 6-11 p.m., Saturday, 11:00 a.m. – 11:00 p.m., Sunday, 11 a.m. – 8 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 normal rides, games, and foods but adds one-of-a-kind vendors to find that special gift for yourself or someone you care about!