Things to do in Boston this weekend of May 26 | Boston Calling 2023

Things to do in Boston this weekend of May 26 | Image credit: Boston Calling Music Festival

Our picks for fun things to do in Boston this weekend of May 26 – 28 include Boston Calling 202346th Annual Festival of the ArtsSomerville’s Memorial Day Parade, and more! 

There’s always lots going on in Boston in terms of events and activities. There are fun things to do in Boston for adults and also Things to do in Boston with family. Our weekly round-up brings you the best things to do in Boston this weekend.

Editor’s Note: Our staff at makes every effort to bring you the latest updates on activities, entertainment, food and drink specials in the Greater Boston area. However, all information is subject to change by the organizers. As always, please confirm before you make your plans!

For more on the latest in Boston, check out our Things to do in Boston this Week and our Things to do in Boston this Weekend with Family guides. These are also updated every week with the best on entertainment, food & drink and deals across Greater Boston! 

Also, check out our articles on Memorial Day Events in Boston 2023, Memorial Day Sales in Boston, Boston Student Discounts for 2023, and Best Hike and Bike Paths in Boston!

Get the lowest price on must-see attractions in Boston with Boston CityPASS

Experience Boston’s must-see tourist attractions — and enjoy considerable savings — on this exciting Boston CityPASS. Visit the popular New England Aquarium and the Museum of Science. Plus choose 2 admissions between the following 3 attractions Boston Harbor Cruises, Harvard Museum of Natural History or the Franklin Park Zoo to complete the experience.

This Boston CityPASS is valid for 9 consecutive days from date of first use. Convenient mobile tickets are valid for 1 year from the date of purchase. Transportation to and from the attractions is not included. Attractions may be required to verify proof of COVID-19 vaccination before allowing entry. Please review attraction requirements before visiting Boston.

Get all the details and book your Boston CityPASS TODAY!!!

Editor’s Note: It’s Memorial Day Weekend! Check out our articles on Memorial Day Sales in Boston – over 60 verified deals & discounts, and Memorial Day events in Boston 2023! Enjoy discounts and fun activities with the family!

Things to do in Boston this weekend of May 26, 2023 – Friday

Memorial Day Flag Garden

Memorial Day Events in Boston 2023 - Memorial Day Flag Garden

Things to do in Boston this Weekend of May 26 | Image Credit:

Our signature community-building event!  Since 2010, they and hundreds of volunteers have created a majestic garden of flags on Boston Common for Memorial Day weekend.  Each of the 37,000+ flags they planted every year at the Soldiers and Sailors Monument represents every brave Massachusetts service member who gave his or her life defending our country since the Revolutionary War. The completed garden is a breathtaking tribute to the true meaning of Memorial Day and a powerful message of community support to the families of these fallen heroes that their sacrifices will never be forgotten.

 When: Thursday – Monday, May 25-29, 2023
Where: 139 Tremont St, Boston, MA 02111
How Much: Not Stated

Boston Calling 2023

Things to do in Boston this weekend of May 26 | Boston Calling 2023

Things to do in Boston this Weekend of May 26 | Image credit: Boston Calling Music Festival

Get ready for an unforgettable weekend at Boston Calling 2023! Taking place over Memorial Day Weekend, this music festival promises an incredible lineup featuring some of the biggest names in the industry. Prepare to rock out to electrifying performances by Foo Fighters, The Lumineers, Paramore, Yeah Yeah Yeahs, Alanis Morissette, Queens of the Stoneage, and many other talented artists. Plus, over 30 Food Vendors will be there to complete the festival vibe!

When: Friday – Monday, May 26-29, 2023
Where: 65 N Harvard St, Boston, MA 02134
How Much: Ticket prices vary. Check here for information.

Ben and Jerry’s Sugar and Waffle Cone Art Event

Head on over to Ben and Jerry’s this weekend and celebrate as they host their sugar and waffle cone art! There will be nature-themed and edible art by Linda Khachadurian. And for every ice cream sale, Ben and Jerry’s Boston Scoop shops will donate $1 to the Avedisian School in Yerevan. Funds will help them run tuition-free for all those who want to attend.

When: Friday – Monday, May 26, 2023, 5 pm – 7 pm
Where: Ben and Jerry’s, 174 Newbury St, Boston, MA 02116
How Much: Free

Get The Lowest Price On The Very Popular Boston Hop On Hop Off Trolley Tour

Free Museums in Boston - Hop On Hop Off Trolley Tour

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.

Board one of the orange-and-green trolleys at any of the stops and enjoy the view with live commentary from an expert guide who knows the city inside and out. Learn about the history and happenings of Boston, a city known as the Cradle of Liberty, as the trolley rolls along from one location to the next. For one, or two consecutive days, hop off at any of the attractions for a closer look, then hop back on when it’s convenient.

14 stops and 33 points of interest!

Get all the details and book your Boston Hop On Hop Off Trolley Tour  TODAY!!!

Things to do in Boston on Saturday, May 27, 2023

46th Annual Festival of the Arts

Memorial Day Events in Boston 2023 - 46th Annual Festival of the Arts

Image Credit: North River Arts Society FB Page

They are thrilled to announce the beloved Festival of the Arts is back, in person, with all their traditional events, entertainment, and offerings! The 45th Annual Festival of the Arts will be held on Memorial Day weekend, May 27 & 28, from 10 am to 5 pm with a Preview Party Fundraiser Friday, May 26, from 7 – 10 pm.

When: Saturday and Sunday, May 27 and 28, 2023 | 10:00 am – 5:00 pm
Where:157 Old Main St, Marshfield Hills, MA 02051
How Much: Free

Chestnut Hill Reservoir Historic Walking Tour

Learn more about the 150-year-old Chesnut Hill Reservoir and the historic structures around it in this one-hour walking tour. Here, you’ll get to see the diverse architectural examples of Boston’s golden age, hear how the reservoir has changed and developed over time, and discover how it works. 

Please make sure to dress accordingly for the weather. 

When: Saturday, May 27, 2023 | 9 am – 10 am
Where:Metropolitan Waterworks Museum, 2450 Beacon St, Chestnut Hill, MA 02467
How Much: $15

Future Spirit Festival

Enjoy tons of great music and tons of fun activities all weekend long in this live music event that hopes to revolutionize the industry! 

In the 200-acre farm venue, there will be 4 music stages and 50+ DJs, free activities all day every day, free camping, free water and shade, vendors and food markets, holistic activities and workshops, and bass and melodic EDM. Invite your friends now!

When: Saturday – Monday, May 27 – 29, 2023 | 9 am
Where:Windy Knob Farm, 140 Causeway St, Millis, MA 02054
How Much: $99

Get the lowest price on the highly-rated Original Boston Guided Brewery Tour 

Learn about Boston’s thriving craft beer scene and sample a variety of libations on this morning or evening brewery tour. Get an inside look at how beer is made and learn about their operations as you visit breweries, cider houses, and distilleries. Visit brewpubs that may include the well-known Samuel Adams or gastropub Meadhall. Round-trip transportation in downtown Boston by air-conditioned van is included.

Get to know Boston’s thriving beer scene on a morning or evening brew tour. Chat with brewery owners and learn about the equipment used to make beer, the brewing process and best of all, what the different kinds of beer taste like.

Get all the details and book your Original Boston Guided Brewery Tour  TODAY!!!

Things to do in Boston this Weekend of May 26, 2023 – Sunday

Afternoon of Brass #2: WORCESTER: Memorial Weekend Spectacular!

They’re excited to present a patriotic-themed concert series featuring members of the Boston Symphony and Pops Brass!  Concertgoers can expect a spectacular and rousing flag-waving experience with unparalleled music at this family-friendly event as we present emotionally-charged music especially suited to Memorial Day.

When:  Sunday, May 28, 2023
Where:  Mechanics Hall, 321 Main St, Worcester, MA 01608
How Much: $33 – $66

Memorial Day Weekend ‘Merica All Day Party

Have a SUNDAY FUNDAY at Loretta’s this long weekend! They are hosting a full music line from 11 am-1 am with their ‘Merica All Day Party!
When: Sunday and Monday, May 28 and 29, 2023 
Where: 1 Lansdowne St, Boston, MA 02215
How Much: Free

Foodscape: An Immersive Public Art Experience 

Foodscape: An Immersive Public Art Experience 

Image credit: Rose Kennedy Greenway

Get to experience the rich ecosystem of Israel while staying in Boston with Foodscape! Created by two Israeli artists, Carmel Beer and Michal Evytar, this multisensory experience will guide you to explore the diverse vegetation and flavors of Israel. You’ll get to wander through a 3000 sq ft. field installed at the Greenway filled with herbs that grow all across Israel. You can also watch as the artists sow and harvest the herbs to create a refreshing glass of gazoz, an Israeli soda. 

When:  Sunday, May 28, 2023, 12 pm – 4 pm
Where: Rose Kennedy Greenway, Atlantic Ave, Boston, MA 02109
How Much: Free

Somerville’s Memorial Day Parade

Things to do in Boston this weekend of May 26 | Somerville's Memorial Day Parade

Image credit: Somerville VETS

Somerville’s Memorial Day Parade is back! The parade will start at noon from Davis Square and proceed west on Holland Street through Teele Square and onto Broadway. It’ll end at the Veterans Cemetery. The ceremony will also feature a wreath-laying and remarks by Mayor Ballantyne. The parade will immediately be followed by the city’s remembrance ceremony.

When:  Sunday, May 28, 2023, 12 pm – 2 pm
Where: Davis Square, 1 Davis Square, Somerville, MA 02144
How Much: Free

Stay on top of the latest events & activities in the Boston area with our weekly updates to Things to do in Boston this Week, Things to do in Boston this Weekend, and Things to do in Boston this Weekend with Family! 

And to get these updates directly to your mailbox, you can follow us on Facebook by clicking the …next to the search icon lens.

Latest posts by Liezel L. (see all)