Strawberry Festivals, Road Races, Art Shows, Block Parties and Juneteenth Celebrations Happening This Month

June in Fairfield County has a full community calendar going on alongside the beach days and concerts. Block parties, road races, art festivals, food events, and Juneteenth celebrations all happen this month across the county. Here's what's worth showing up for.

Festivals and Community Gatherings

Stratford Day / Main Street Festival – Saturday June 6, 10AM to 4PM on Main Street. Rides, games, food, local vendors, full street fair energy.

Greenwich Police Department Benefit Car Show – June 6 at 10AM at Town Hall. A fun morning if you appreciate classic cars.

Athletic Brewing Co. Fairfield Road Races (Half Marathon and 5K) – June 6 and 7, starting at 8AM at Jennings Beach. One of the better local race courses and a great spectator spot too.

Fairfield Summer Saturdays on the Museum Commons – Family crafts, lawn games, and rotating food trucks every Saturday throughout June. Easy, free, and good for kids.

Brookfield Town Block Party – Sunday June 7 at Brookfield Town Center.

Norwalk Art Festival – June 20 and 21 at Mathews Park. One of the largest juried outdoor art shows in New England. Worth making a day of it.

Westport Rotary Great Duck Race – Saturday June 27 at Parker Harding Plaza on the Downtown Westport riverfront. The 16th annual. Fun, quirky, very Westport.

Westport Sidewalk Sale – June 26 through 28 in Downtown Westport.

Fairfield Dog Days – Sunday June 28 at 11AM at Old Town Hall Green. Dogs very much welcome.

Food Events

Taste of Westport 20th Anniversary – Wednesday June 3 at the Fairfield County Hunt Club. Twenty years in and it's still one of the best food events of the summer.

Lyman Orchards Strawberry Festival – Saturday June 13 at the Apple Barrel Farm Market in Middlefield. Fresh strawberries, farm setting, worth the drive.

Monroe Strawberry Festival – June 20 and 21 at Monroe Town Green. Relaxed, local, and delicious.

Cocktails and Clams at Earthplace – June 6 at 5PM in Westport. A good excuse to get outside on a Friday evening.

Arts and Culture

Stamford Arts and Crafts on Bedford – Kicks off June 16 and runs through September in Downtown Stamford. A great weekly reason to wander.

Connecticut Open House Day – Saturday June 13. Free or discounted admission at museums and historic sites across the state. One of the most underrated days on the calendar.

Stamford Town Center Summer Block Party – June 20 and 21 at the Restaurant Plaza.

Juneteenth Celebrations

Bridgeport Juneteenth Parade and Harambee Festival – June 13 at Seaside Park. A vibrant, meaningful celebration with real community presence.

Fairfield Juneteenth Celebration – Wednesday June 17 at 4PM on the Fairfield Town Green.

Norwalk Juneteenth Celebration Weekend – June 19 through 21 at Veterans Memorial Park.

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