Summer Festivals and Fairs in Fairfield County

Fairs and Festivals in Fairfield County This Summer

Day one of summer vacation and the score in this house is kids 1 million, mom 0. While I dreamed of three freshly scrubbed, idyllic children working together on community service projects and requesting additional math assignments, the reality is the trio argues over, well… everything. Who gets the pink spoon, who gets the cow mug, who gets to grab yesterday’s mail out the box... and this is only the very first day of school break! Clearly, Operation Get the Heck Out of the House needs to be kicked into high gear. And what better way to keep kids of all ages and interests occupied than local fairs and festivals? If you're up for a day trip, we've rounded up fun summer fetes in Hartford and New Haven counties, as well as Eastern Connecticut. But if you prefer a fest right here in your own Fairfield County backyard, read on.

46th Annual Strawberry Festival - Monroe
Saturday, June 17-Sunday, June 18, 2017
Celebrate strawberry season with this juried crafts show complete with strawberry shortcake, strawberry pie, children's games, and music.

34 Church Street, Monroe

Rowayton River Ramble - Rowayton
Saturday, July 8th
This 46th annual tradition is a day of fun and festivity for kids and adults. There are plenty of fun games and activities on Five Mile River, such as the petting zoo, bouncy castle, giant water slide, obstacle course, face painting, and the ever-popular dunk tank.

Pinkney Park, Rowayton Avenue, Norwalk 

Darien Sidewalk Sale and Family Fun Days - Darien
Thursday, July 6th-Saturday, July 8th
Visit the Goodwives Shopping Center and merchants around Darien for a few days of shopping, live music, bouncy castles, and lots of kid fun. Food, fun, and bargains galore.

25 Old Kings Highway North, Darien

Village Fair and Sidewalk Sale - New Canaan
Saturday, July 14-15th
Sponsored annually for more than 50 years by the Chamber of Commerce, this fair offers local residents and regional visitors an action-packed, bargain-filled, entertaining, and delicious way to spend a summer day in one of the most charming towns in Connecticut. In addition to sales and discounts, there will be live music, magic shows, and face painting for the kids. 

Downtown, Elm Street, New Canaan

Originally published June 13, 2015.

Goodwives Shopping Center
25 Old King's Highway
06820 Darien , CT 41° 4' 42.9096" N, 73° 27' 52.5276" W
Mill River Park
Mill River Street
06902 Stamford , CT
Phone: 203.696.4760
41° 3' 14.2056" N, 73° 32' 46.752" W
McLevy Green
Bank Street
06604 Bridgeport , CT
Phone: 203.578.3972
41° 10' 38.3664" N, 73° 11' 20.094" W
Downtown New Canaan
Elm Street
06840 New Canaan , CT 41° 8' 45.2796" N, 73° 29' 52.3428" W
Pinkney Park
Rowayton Avenue
06853 Rowayton , CT 41° 4' 16.8312" N, 73° 26' 39.7392" W
Monroe Congregational Church
34 Church Street
06468 Monroe , CT 41° 19' 58.5624" N, 73° 12' 24.3864" W
Slide the City
100 Prospect Street
06901 Stamford , CT 41° 3' 32.67" N, 73° 32' 8.8548" W