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Things to Do in Boston in May

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This post lists top things to do in Boston in May, updated for 2020, including free, nighttime, as well as family-friendly activities and events. 


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Disclosure: While our recommendations are always unbiased, we may receive a small share of sales through some of the links below at no cost to you. See the full text.


This section covers our top ten list for May. You might also read our post on things to do in Boston (at any time of the year).

For more ideas on popular things to do in Boston, check out our popular posts:

Some of the items listed in this post are included for free with the purchase of a tourist discount pass.

(1) Catch a Concert

Boston has some fantastic music venues, which means big names come through quite often. We list the highlights of the month below the video.

See who is else is performing in Boston this month on StubHub.



Check out what other concerts you can see in Boston this month on StubHub.

(2) Go to a Sporting Event

Boston’s home teams are very well-known. And in May, there are plenty of games to attend! Baseball season is in full swing and hockey is in their playoff season.

Going to a sports event is a good way to keep kids entertained if you are traveling with them. They might also like a tour of Fenway Park.






Stubhub has a schedule of what other games are on this May

For other family-friendly activities, check out our things to do with kids section below.

(3) Go on a Sightseeing Tour

You can learn about the city’s history and the country’s history on our pay-what-you-like Freedom Trail Tour.

Or if you’re interested in Little Italy, we have a pay-what-you-like North End Tour too.


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If you want to cover more ground, you should also check out:

Boston has such a wide variety of tours available - there’s something for everyone!

(4) Have an Evening at the Theatre

Boston's Emerson Colonial Theater has some entertaining traveling Broadway shows coming through this May!

Chicago The Musical! will be in town from May 5-May 10, 2020. On the 9th and 10th, there are two shows a day (matinee and night).

Fans of modern dance can see the renowned Alvin Ailey American Dance Theater perform on May 1, 2, 3, and 9, 2020. 

(5) Nantucket Wine Festival 

One of the most coveted wine festivals in the country, the Nantucket Wine Festival takes place on May 13-17, 2020.

With a daily array of tastings and events, there is something for all wine connoisseurs!



Set on the historic and quaint New England island of Nantucket, this is an event you will never forget.

Additional activities include seminars and a culinary village. Note that this event is 21+. Ticket prices vary per event. 

(6) Save Money With a Tourist Pass

If you want to see multiple popular attractions while in Boston, you could save a significant amount of money by purchasing a city pass upfront.

Boston currently has several different types of passes to choose from, and they each include a lot of popular activities including tours, museums, cruises, and other things to do.


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Here are a few of the most popular tours, museums, and other things to do included with these passes:

Depending on which type of pass you choose, you should be able to save at least 20% – 50% off or more from retail prices.

For additional details, please read our post covering Boston tourist passes.

(7) Boston Calling Music Festival 

This is one of Boston's biggest and best music festivals! From May 22-24, 2020, at the Harvard Music Complex, music fans can enjoy a plethora of bands and artists.



In 2020, the line up includes the Foo Fighters, Rage Against the Machine the Red Hot Chili Peppers.

Get tickets here on StubHub.

For more evening activities, check out our things to do at night section.

(8) Enjoy a Martha’s Vineyard Day Trip!

A gem among Boston locals and tourists alike, the New England summer colony of Martha's Vineyard has been a longtime favorite.

Located just south of Cape Cod, the island boasts beaches, farmland, lighthouses and quaint harbor towns.



Plus, delicious eateries, gingerbread cottages, and beautiful hydrangeas when they’re in bloom.

There are multiple ways to get to Martha’s Vineyard. For more information click here.

(9) See the Garden of Flags on Memorial Day 

A day honoring those who have died serving our country in addition to being the unofficial kickoff to summer, Memorial Day is a day well spent in Boston.

In 2020, Memorial Day falls on May 25.



On May 25 at 1 pm, 37,000 small American flags will be placed in Boston Commons by the Massachusetts Military Heroes organization.

This is to commemorate every Massachusetts service member killed defending his/her country. It is free to see the flags.

For more memorial day activities in Boston, click here.

(10) Eat in the North End

Home to Boston’s “Little Italy”, the old and narrow streets of the North End are chock full of delicious and often family-owned & operated Italian eateries.



A must-try is famous Mike’s Pastry where you can devour one of their numerous delicious homemade cannolis.

Walk off the calories by joining our North End/ Little Italy tour.


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Evenings in May in Boston are pleasant and there are a lot of activities happening!

Some night activities listed in the top 10 include seeing a Red Sox game, going to the theater or a concert, such as the Boston Calling Music Festival.

Below are more evening events to keep you busy in May!

For additional evening ideas, please read our full post covering things to do at night in Boston.


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For additional ideas, check our full post covering things to do at night in Boston.

Enjoy a Ghosts and Gravestones Tour 

Hop aboard the “trolley of the doomed” and join your host on an approximate two-hour tour learning Boston’s deepest, darkest secrets that are sure to be filled with murder and mayhem!

Stops on tour will include various Boston graveyards--some of the oldest in the US among other places. Tickets from $39.90; parental guidance encouraged for children under the age of 13.

More information here.

Laugh with Bill Maher

Love your politics with a big side dose of witty humor? Then Bill Maher is for you! 

He will be performing his stand-up comedy on  May 30, 2020, at Boch Wang Center Boston. You can get tickets for Bill Maher on StubHub.

If Maher is a bit too intense for you, there are always other comedy shows in Boston. 

See who else is in performing stand-up comedy Boston this month on StubHub.

Experience the Boston Symphony Orchestra

If you are a classical music lover, you will be enthralled by the Boston Symphony Orchestra.

In May 2020, you can catch them at the historic Symphony Hall on May 1.

You may also want to consider taking a free tour of the Symphony Hall. These tours are offered either on a day without any scheduled performances or before/after a concert. All you have to do is sign up ahead of time!

See the City from the Water 

May nights are lovely for an evening cruise in Boston. There are several different companies that offer sunset or dinner cruises on the harbor.

Whichever you choose all allow you to see the city skyline and lights as the sun goes down.

If you want to learn more about these opportunities, make sure to read our post covering Boston boat tours.

TIP: Both the Boston City PASS and the Go Boston Card include at least one free cruise.

Celebrate Cinco de Mayo

Grab your sombrero and get ready for a weekend of fun celebrating Cinco de Mayo!

Join a pub crawl or take a 5th of May themed boat cruise. Be sure to check locals pubs and restaurants for a drink, food, and music specials.

The city is sure to be busy with party-goers so be ready for big crowds at the city’s pubs!


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Boston offers lots of free activities and sights. Two activities mentioned above include seeing the Garden of Flags and taking a free tour of the Symphony Hall


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Below are some free activities. To see even more ideas, check out our full Free Things to Do in Boston article.

Boston Public Gardens

Located in the heart of Boston and adjacent to Boston Commons, the Boston Public Gardens have been around since 1837. (See video above),

Filled with colorful plants and flowers, statues, and water features the gardens are a lovely spot for an afternoon walk. Don’t forget to see the swan boats and even take a ride if you’re so inclined!

MayFair at Harvard Square

At this annual Boston favorite, you can enjoy a day of free activities. In 2020, the event is on May 17. 

Highlights include live music, dance, and street performers, arts & crafts vendors, vintage goods for sale, and food from around the globe.

See the Harvard Square website for all the details.

ArtWeek Boston  

From May 1-10, 2020, you can attend Boston's ArtWeek which offers dozens of fun and interactive experiences at a number of sites including small businesses, libraries, historic sites, hotels, and restaurants.

Many of the events are free, though some charge an admission fee.

Check the ArtWeek website for more information and a calendar of events.

Visit a Free Museum

If you miss ArtWeek, or just can't get enough art onto your life, you are going to love Boston.

There are several great museums in Boston that offer free admission.  

Find out which museums you can see without paying a dime from our full post covering free museums in Boston.

Take a Free Tour of the New Massachusetts State House

There is nothing new about the New Massachusetts State House. It was built in 1798!

On land that was once owned by John Hancock, it's the oldest building on Beacon Hill in Boston.

You can take a free tour of this historic building Monday to Friday throughout the year from 10:00 am to 3:30 pm.

Tours last approximately 30-45 minutes and include an overview of the history and architecture of the State Capitol. 

Read more about these free tours here.

This and the other sites on the Freedom Trail are covered on our Freedom Trail guided tour!

Find more free activities from our post covering free things to do in Boston.


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Families of all ages will find dozens of fun things to do in the city of Boston. 

The free MayFair listed above is open to all ages as is taking a stroll through the Boston Public Gardens.



Here are a few more activities that are family-friendly. Don't forget our full family-friendly article!

See the Duckling Parade 

Celebrate the classic children’s book “Make Way for Ducklings,” at the annual Duckling Day Parade. In 2020, the parade is set for May 10.

This event draws over 1,000 people for a parade through the city’s public gardens dressed as characters from the book.

Prior to the beginning of the parade, enjoy a number of family activities on Boston Common including crafts, face painting, circus games, and a magician.

Catch a Red Sox Game

With one of the biggest fanbases in the country and a stadium that is the oldest in Major League Baseball, catching a Boston Red Sox game at Fenway Park is the biggest highlight for many visitors to Boston.

The team has plenty of home games in the month of May but act fast on tickets, as they can easily sell out.

You can also tour the historic Fenway ballpark, read our post for advice.

Visit the New England Aquarium

Welcoming visitors for over 50 years, the New England Aquarium is one of the most popular tourist attractions in Boston.

See penguins, seals, dozens of different fish and meet the aquarium's most famous resident, Myrtle the Green Sea Turtle!

Ride a Rollercoaster at Six Flags New England

This popular amusement park is now opened for the season! This is a family favorite with rides suitable for people of all ages and sizes!  

Although tickets can get expensive, it’s worth noting that admission is actually included with the Go Boston Card. Considering that tickets can cost more than $70 per person on their own, even a 1-day tourist pass would cost less at $59!

Eat at Faneuil Hall Marketplace

Faneuil Hall Marketplace is an excellent location that is appealing to all ages. You can find anything for that fussy little eater!

In addition to dining, look out for street performers and musicians, there’s always something fun to watch! The marketplace is open daily and hours vary.

Mother’s Day 

Make Mom feel special on May 10, 2020. Check local restaurants for special Mother’s Day Brunch menus, take Mom shopping on the famous Newbury Street.

For something different, join docent volunteers on an hour and a half walk through Mount Auburn Cemetery while visiting the graves of some more notable mothers buried there--including Julia Ward Howe.

Visit the Museum of Fine Arts

First opened to the public on July 4th, 1876, Boston’s Museum of Fine Arts now holds over 450,000 pieces in its collection.

Featuring art from all over the world, visitors of the MFA can look forward to European and American classics, photography, drawings & prints, sculpture and contemporary art as well.

The museum is open daily from 10 am-5 pm with extended hours from 10 am-10 pm Weds-Fri. Tickets for adults are $25; child ticket prices vary.

Be sure to read our post covering things to do with kids in Boston for more ideas.


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About The Author

Brian Burgess

Brian was born in Cambridge and has been living in the Boston area all his life. He is a graduate of Boston's Emerson College with a degree in communications with a journalism/history focus. He has been leading tours for Free Tours By Foot Boston since it was started in the city of Boston in 2012, and enjoys sharing his knowledge of Boston's rich history with not only the guests on his tours, but with everyone he meets.
Updated: October 12th, 2021
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