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.

Ethos Greek Festival - Stamford
Thursday June 1 - Sunday June 4, 2017
From authentic Greek fare to rides and games with Stewart Amusement, the Ethos Greek Festival in Stamford will have plenty of fun for the whole family. 

1230 Newfield Avenue Stamford 06905

Teddy Bear Festival - New Milford
June 3, 2017
Hosted by the Women's Club of Greater New Milford, the 18th annual Teddy Bear Festival will be held on the town green from 10-3. Enjoy a teddy bear parade, teddy bear hospital and visit from Smoky the Bear himself, escorted on the firetruck.

Town Green, New Milford 06776

Soupstock - Shelton

Image courtesy of Tina Marie Photography via Soupstock

Saturday Jun 10-Sunday June 11, 2017
Celebrate music, art, food, and crafts at Veteran's Memorial Park in downtown Shelton at the 8th annual Soupstock Festival. Enjoy music from two stages, a Kid's Zone with bounce houses, arts and crafts and hula-hooping from 11am-5pm, and sample delicious soups and chili at the annual Soupstock Soup and Chili cook-off.

38 Canal Street E, Shelton 06484
Pirate Day - Milford
Sunday June 11, 2017
Ahoy Matey's! Join the rest of the scaliwags for a family-friendly day of adventure, treasure-hunting and a swashbuckling good time! Start the day with Pancakes with Pirates and stay for the arrival of Captain Kidd himself as he arrives aboard "Oz" in Milford Harbor. 
5 Broad Street, Milford 06460
Thursday June 15-Sunday June 18, 2017
Enjoy amusement rides, Touch-A-Boat, sand art, musical performances, an international food court and more at Westport's carnival-style Yankee Doodle Fair on the grounds of the Westport Women's Club.
44 Imperial Avenue Westport 06880
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

Weed Beach Festival - Darien
Saturday June 17, 2017
Kick off the summer at Weed Beach with three great bands, inflatable slides, sailboat rides, kayak and paddle board rentals and kids activities in the Kids Cove.

Nearwater Avenue Darien  06820

Family Fun Day - Fairfield
Saturday June 17, 2017
The Pilot House in Fairfield is hosting its 3rd Annual Family Fun Day from 12-5pm. Enjoy bounce houses, games and food.

240 Colony Street Fairfield 06824

Rowayton River Ramble - Rowayton
Saturday, July 8, 2017
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 06853

Darien Sidewalk Sale and Family Fun Days - Darien
Thursday, July 6 - Saturday, July 8, 2017
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 06820

NICE Festival - Norwalk

Image courtesy of NICE Festival
Saturday July 8, 2017
The Norwalk International Culutural Exchange is hosting its second annual NICE Festival to celebrate global heritage and culture through music, food, art, and talent. The NICE Festival will feature dancers, musicians, food, and craft vendors. Children's activities will take place 12-4pm. Proceeds from the festival will support local charitable organizations and their fight against poverty, hunger, and slavery.

Oyster Shell Park Norwalk 06855

Village Fair and Sidewalk Sale - New Canaan
Saturday, July 14- Sunday, July 15, 2017
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 06840

Easton's Annual Fireman's Carnival - Easton
Tuesday August 1 - Saturday August 5, 2017
Head to Easton's Annual Fireman's Carnival the first week of August for an old-fashioned local carnival that appeals to all ages. Grab a seat on the bumper cars, The Ali-Baba Swing or The Cliff Hanger. 

1 Center Road Easton 06612

Milford Oyster Festival - Milford
Saturday August 19, 2017
With fun for all ages, Milford's 34rd annual Oyster Festival features plenty of fun activities for the kiddos. Enjoy tunes from children's musician Al DeCant on the children's stage, watch performances from Lee Lund Dance Studio and The Magic of Jeffrey and demonstrations from Packard Martial Arts. Grab a wristband for unlimited rides at the amusement rides and enjoy plenty of delicious food.

Downtown, Broad Street, Milford 06460

St. Leo Fair - Stamford
Tuesday August 29 - Sunday September 2, 2017
Sample international foods, enjoy carnival rides and try your luck at The Bingo Parlor at the St. Leo Fair. Plus, there will be live music each night starting at 7:30pm in the Lion's Den. 

24 Roxbury Road Stamford 06902

Norwalk Oyster Festival - Norwalk

Image courtesy of Ally Noel

Friday September 8th-Sunday September 10th
Join the Norwalk Seaport Association's 40th annual Oyster Festival for three days of entertainment, arts and crafts, and great food. The Kid's Cove will host children's activities on both Saturday and Sunday including karate demonstrations, variety shows,and  character meet and greets.

132 Water Street Norwalk 06854

Originally published June 13, 2015.

Cover photo courtesy of the NICE Festival 

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