June Events
Ice Cream Social @ New Canaan Museum & Historical Society
Sunday, May 31st, 11-3PM
Join us on the great lawn at the Historical Society for an afternoon of antique and classic cars, old-fashioned games, children’s activities, live music by the New Canaan Town Band, complimentary ice cream and cake, museum tours, and the chance to win the People’s Choice Award!
2026 Yankee Doodle Fair
June 18th – June 21st (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 annual YANKEE DOODLE FAIR.
This year’s family Fair kicks off on:
- June 18th (6pm – 10 pm)
- June 19th (6pm – 10pm)
- June 20th (1pm – 10pm)
- June 21st (1pm – 5pm)
Carnival rides and games by Stewart Amusements will be featured throughout the weekend, with unlimited ride wristbands available daily.
New this year, the Fair will host an Inclusive Sensory Hour on Sunday, June 21 from 12–1 p.m., offering a quieter, lower-sensory experience for neurodiverse guests and families before general admission begins.
Weekend entertainment this year will include performances by Melissa Wasserman and Late 4 Dinner!
Kids Fest at Lake Compounce
CT Irish Festival & Field Day Weekend
The CT Irish Festival will be held June 13–14 at the Irish American Community Center in East Haven, featuring live entertainment, children’s activities, competitions, Irish food and drinks, Gaelic sports, and shopping!
Midsummer Fantasy Renaissance Faire – CT
June 27-28, July 4-5, and July 11-12 from 11AM – 6:30PM
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 ‘26 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 13th, 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 10-13, 6-10 p.m. Two years ago 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 26-27, Friday 6:30-10:30 p.m., Saturday 2-10:30 p.m.
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, June 27th, 10 AM – 4 PM!
Activities:
- 8 AM – 4:30 PM: Pick Your Own Raspberries, located on South Street
- 9 AM – 4 PM: Apple Barrel Deli Open
- 10 AM – 4 PM: ToneGrown with Kids Crafts on the Patio
- 10 AM – 4 PM: Face Painting by Lara
- 10 AM – 4 PM: Silhouette Portraits with The Silhouette Lady
- 10 AM – 4 PM: Circle K Petting Farm
- 10 AM – 4 PM: Roaming Railroad Trackless Train
- 10 AM – 3:30 PM: Horse-Drawn Wagon Rides
- 10 AM – 5:30 PM: Ice Cream Window Open on the Apple Barrel Patio (with a special raspberry themed sundae!)
- 11 AM – 3 PM: Food Trucks (Crazy Taco Mex & Jeff’s Kettle Corn)
- 1 PM – 4 PM: Live Music from the Aquatudes*
*Free activities!
Admission to the Lyman Orchards Raspberry Festival is FREE!
Westport Sidewalk Sale
Westport’s Sidewalk Sale is back June 26–28, 2026, 10 AM–5 PM—and it’s packed with can’t-miss deals!!
Downtown Westport will be buzzing with huge markdowns, sidewalk racks, and surprise specials from local favorites like Jenni Kayne and Madewell—perfect for refreshing your summer wardrobe!! Plus, the Huntington Learning Center will have games and prizes, and you can browse book deals at Westport Book Shop and The Westport Library for the perfect summer read.
Don’t miss it!
July Events
Westport Fireworks!
Join the Westport community for one of our favorite summer traditions as our town celebrates Independence Day with a spectacular fireworks show at Compo Beach on Thursday, July 2, 2026 (rain date: Friday, July 3, 2026)! Come out for a fun-filled evening with friends, family, and neighbors!
*****This is a ticketed event. Tickets may be purchased beginning June 1 at the Westport Police Department, 50 Jesup Road, and beginning June 3 at the Parks and Recreation Office, 260 Compo Road South. Cash or check only.
Fairfield Fireworks
Kick off the holiday weekend with the Fairfield community at Jennings and Penfield Beach on Friday, July 3, for a festive evening by the water! Their spectacular fireworks display will begin at 9:15 p.m.!
Weston Fireworks
Celebrate the Fourth of July with the Weston community at the Bell Ringing Ceremony and Patriotic Tailgating Contest at Weston Middle School Field! Gates open at 4:30 p.m., with fireworks lighting up the night sky at 9:20 p.m!
St. Catherine Siena Carnival of Fun
St. Catherine’s Church, Riverside, CT; July 11-15th, 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 28th-August 1st, 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 26-29th, Wednesday to Friday, 6-10 p.m., Saturday, 5-10 p.m. Fun and games galore!
St. Leo Fair
St. Leo Church, Stamford, CT; September 1st -5th , Tuesday and Wednesday, 6-10 p.m., Thursday and 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 11th-13th, 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 Veterans’ 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!