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Memorial Day Weekend in CT and the Berkshires

With the unofficial start to summer finally upon us, it’s time to break out those shades, heat up the grills and make the most of Memorial Day weekend! Whether relaxing with family and friends in the backyard or heading downtown for a parade and other community fun, there’s plenty to do to keep busy throughout Connecticut and the beautiful Berkshires all weekend long.  Here is a regional roundup of some local happenings that you won’t want to miss.


Fairfield County

  • Love rides and games? Check out the Danbury City Fair for some good, old-fashioned fun. This popular annual fair begins Memorial Day weekend, and runs through June 7th.
  • Welcome in the summer by crossing the finish line of Greenwich’s Fixx Memorial Day 5K Race—a town tradition for the past 50 years. For more information, please visit the Threads & Treads website here.
  • Visit the Darien Nature Center for a “barnyard bash” perfect for the entire family.  Enjoy a children’s petting zoo, pony rides, face painting and more.
  • Many beaches around town are opening this weekend! Grab your beach towel and sandals, and head out for the day! Click here for a list of the best local spots.
  • Memorial Day weekend marks “Long Island Sound Day” at the Maritime Aquarium in Norwalk! Stop by to learn the environmental values of the Sound, and see how you can be a better “Sound Steward” in your coastal community.
  • It wouldn’t be Memorial Day weekend without honoring all those brave men and women who have served, and continue to serve this great country! Honor the red, white and blue this weekend by attending one of these community services and parades around town in Fairfield County.

Shoreline CT

  • Welcome in the season with Mystic’s  “Salute to Summer,” a community event in which family and friends take part in vintage lawn games, run relay races, play tug-of-war, make old-fashioned ice cream, play baseball and more. There will even be a nautical-themed, patriotic costume dog parade, so start brainstorming some ideas! For more details on the day’s events, click here.
  • Spread out those blankets and experience a simple afternoon on the beautiful grounds of the Medad Stone Tavern in Guilford, CT at the town’s special Memorial Day Picnic event. From 11:30 AM to 3 PM, enjoy great food, live music, animal rides, pie-eating contests and more—a whole lot of old-world Americana fun! This event immediately follows the annual community parade, which starts at 10 AM on the Guilford Green.

Litchfield County

  • A Memorial Day parade and ceremony will take place at the Litchfield Center at 10 AM on Monday, May 25th. Be sure to stop by and show your patriotic pride!

The Berkshires:

Out in the beautiful Berkshire Mountains, Memorial Day weekend is packed with all sorts of activities and events. From road races and live music to theatre performances, festivals, family hikes and more, here are some fabulous ways to make the most of the holiday weekend.

  • Get ready to run at what is often referred to as the “toughest Marathon in the East!” Other races around Lenox, Stockbridge and Great Barrington include the Tanglewood 10k/5k, the Memorial Day 15k Trail Race, the Memorial Day Dirt Road Ride and more. For race details, click here.
  • Calling all music lovers! Kick off the summer with two days of live music at Tanglewood in Lenox, MA.
  • Put on your hiking shoes and head outside in the great outdoors for a beautiful hike through a mowed floodplain with multiple views of the Housatonic River in Great Barrington, MA. The terrain has little elevation, and is the perfect spot for hikers of all abilities.

For more information on this event and to see other special Memorial Day offerings in the Berkshires, click here.

Have a great Memorial Day Weekend, everyone! 

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