American Flags on Lawn

Celebrate Memorial Day in Boston

Memorial Day is the unofficial start to summer in Boston, a city that eagerly awaits the warmth and sunshine after enduring a grueling New England winter. As the long weekend approaches, Bostonians are ready to embrace outdoor activities and soak up as much sun as possible. While many residents choose to leave the city for the holiday, there are plenty of exciting ways to celebrate for those of us who stay. From honoring our heroes at the Massachusetts Military Heroes Garden of Flags to enjoying the vibrant atmosphere of the Boston Calling Music Festival, the city offers a variety of events and activities to make your Memorial Day memorable.


  • Visit the Massachusetts Military Heroes Garden of Flags. Every year, the MMHF plants a Garden of Flags – 37,000 of them – in front of the Soldiers and Sailors Monument on Boston Common to commemorate each of the Massachusetts service members who have given their lives to defend the United States and our freedom since the Revolutionary War.
  • Check out the Boston Calling Music Festival. This popular three-day outdoor festival features four stages and some of the best acts in live music, with visual arts and a 100-foot ferris wheel to boot. This year’s headliner is Ed Sheeran.
  • Visit a museum (for free). Admissions to the Museum of Fine Arts and the Institute of Contemporary Art are free on Memorial Day.
  • Enjoy the Charles River. Walk the esplanade, go kayaking, or take a sailing lesson.
  • Enjoy a picnic and a swim at Castle Island. While there’s no castle and it’s technically a peninsula, it’s well worth the visit to stroll around the Harborwalk, swim at Castle Island Beach, and explore Fort Independence.
  • Catch a game at Fenway Park. The Red Sox will be playing home games all weekend.

With so many fantastic options to choose from, staying in Boston for Memorial Day weekend can be a delightful experience. Whether you’re exploring the rich history and culture at the city’s museums, enjoying the scenic beauty of the Charles River, or cheering on the Red Sox at Fenway Park, there’s something for everyone. If you need assistance planning your perfect Memorial Day weekend, contact Simplified. Our award-winning concierge service can handle all the details, allowing you to relax and make the most of your holiday. Celebrate this Memorial Day with a mix of reflection, adventure, and enjoyment in the heart of Boston.


Editor’s Note: This post was originally published in May 2017 and has been updated for accuracy and comprehensiveness.