Summer Festivals & Carnivals

By Melissa Cercone, Assistant Publisher, Macaroni Kid Newtown-Monroe-Trumbull, CT June 3, 2021

Summer is back and so are the many town festivals and carnivals that pop up throughout the season!

Live music, good food, local specialties and artisans for the adults. Carnival games and rides, children's entertainment, scavenger hunts and more for the kids. There is something for everyone during the Summer festival season! 

Click on the pink festival/carnival name for more info on each event. The list is in order of date. 

🚦 Stratford Main Street Festival
June 5, 10:00am - 5:00pm
Music, food, vendor booths, games, and children rides! Celebrate the many organizations, programs, and services Stratford has to offer.

🎡 The Danbury Fair Carnival
June 5, 12:00pm - 11:00pm
June 6, 1:00pm - 10:00pm
POP Wristband (Unlimited Rides) $30
Rides, Games, Food, Fun!

🏴‍☠️ Pirate's Day! (Milford)
June 6, 9:00am - 3:00pm
Free for everything but Pancakes with Pirates which costs $15 and requires reservations.
Dress like a pirate, rock out with Rockin’ Ron the Friendly Pirate, and (of course!) watch Captain Kidd & his mutinous crew invade Milford Harbor! Search for pirate booty on a kids’ treasure hunt through town and enjoy arts & crafts, unique vendors, and live music!
Don’t forget to dress like a pirate if you are so inclined! View the event schedule here!

🎡 Wallingford Carnival
June 9-12, 6:00pm - 10:00pm
Food, Games, Crafts, Live Music, Face Painting, Teen, Family & Kiddie Rides.

🍓 Orange Strawberry Festival
June 12, 10:00am - 4:00pm
Delicious food, live music and family fun at the annual Strawberry Festival. The Festival offers crafters and fine arts, live entertainment, children's games, face painting and hayrides, and TONS of food! Pulled pork, hamburgers, hot dogs, sausage and peppers, and of course, strawberry sundaes, chocolate covered strawberries, and luscious strawberry shortcake!

🍓 Monroe Strawberry Festival
June 19, 10:00am - 5:00pm
June 20, 12:00pm - 5:00pm
49th Annual Strawberry Festival Craft Show & Fine Arts! Juried exhibitors, local artists, strawberry shortcake, strawberry pies, baked goods, children's games & live entertainment.

🎡 Newtown Summer Carnival
June 24, 6:00pm - 10:00pm
June 25, 6:00pm - 10:00pm
June 26, 2:00pm - 10:00pm
June 27, 1:00pm - 5:00pm

🎆 Trumbull Day
July 2, 6:30pm - 10:30pm
July 3, 2:00pm - 10:30pm
Admission is free but bracelets will need to be purchased for the carnival rides.
Trumbull Day is a fun-filled family event with food, vendors, carnival rides and games, children's entertainment, a main stage featuring local bands and fireworks.

🎠 Easton Volunteer Fireman's Carnival
August 3 through August 7.
More info coming soon!

🎟 Orange Volunteer Fireman's Carnival
August 5, 6, 7, 8
More info coming soon!

🦪 Milford Oyster Festival
August 20, 6:00pm - 10:00pm
August 21, 10:00am - 6:00pm
Oysters! And other food, carnival rides, live music including a children's stage, children's activities and more!

Know of a festival or carnival in the area that is not on this list? We welcome all feedback/suggestions! Just email us

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Macaroni Kid Fairfield-Trumbull-Shelton is a free weekly newsletter and website focused on fun family events and information in our area specifically: Monroe, Trumbull, Easton, Fairfield, Shelton, Derby, Ansonia and Seymour. We gather together all kinds of local family events and activities each week, and add useful information about classes, family-focused businesses, event and product reviews, recipes, crafts, school and camp guides and more.