Fun Things to Do in Boston in May

Top 10 Boston events for May

You'll find lots of interesting things to do in Boston in May.  Go to the Diana Ross concert at the Wang Center, cheer the Red Sox at Fenway Park, and head to Boston's comedy clubs for non-stop laughs.

Boston hotel rates are lower in May than during the summer, so this is also an affordable time to visit the city.  Tour Boston by bike, go on a Harbor cruise, go sailing, walk along the Freedom Trail, visit art galleries - these are just a few of the fun things to do in Boston in May.

Best of all, May is the month when warm weather reliably returns - at least on some days - so go outside and enjoy it! 

Rhododendrons in "hidden" garden in Boston's Back Bay neighborhood

10 best things to do in Boston in May

1.  Enjoy all the flowers

One of the top things to do in Boston in May is simply to walk around Boston's neighborhoods and enjoy all the flowering trees, shrubs, and bulbs.  Although each neighborhood is gorgeous during May, Back Bay is especially spectacular. 

Walk along Beacon and Marlborough Streets to admire the beautiful front pocket gardens and glimpse "hidden" gardens, like the one in the photo.  Or stroll along Commonwealth Mall going east to the Public Garden, where you'll find even more spring color.

2.  Visit some art galleries

If you want to look at more than just flowers while you stroll around Back Bay, May is the perfect time to combine your walk with a tour of Newbury Street art galleries. 

SoWa Open Markets, in Boston's trendy South End neighborhood, opens for the season in May with outdoor displays by indie artists and designers - we love to spend Sunday afternoons browsing among the market's white tents, and treat ourselves to a great dinner at one of the South End restaurants.

3.  Cheer for the Red Sox 

Whether you're visiting Boston or live here, one of the best things to do in Boston in May is to head for Fenway Park and cheer for the Boston Red Sox. 

No tickets?  Check Check out StubHub!, a buyer-seller marketplace owned by eBay which the Red Sox recommend as the place for season ticket holders to sell tickets they can't use.  You can usually find great seats and interesting deals here.

Boston Red Sox schedule

If you're coming into town just for a game, check out hotels near Fenway Park, as well as Fenway restaurants and area nightlife.

4.  Tour Boston by bike

Visiting Boston and looking for a unique way to tour the city?  Go on a Boston bike tour - several groups offer them, or you can rent a bike but head out on your own.  Do be careful of Boston drivers!

5.  Tour the Freedom Trail

Whether this is your first trip to Boston or your 50th - or perhaps you even live here - one of the best ways to see some of the most interesting areas of the city is by following the Freedom Trail, Boston's walk through history.

Don't want to walk the whole 2.5 miles?  The Freedom Trail goes through 3 neighborhoods - historic downtown, the North End, and Charlestown - so pick one and explore that part of the trail.  Or check out other Boston attractions.

6.  Join the Ducklings Day Parade

If you're traveling to Boston with children, take part in this beloved annual event, based on Make Way for Ducklings by Robert McCluskey.  You'll following the trail of Mr. and Mrs. Mallard and their 8 ducklings as they make toward Boston's Public Garden.  For even more fun, come dressed as your favorite character.  Check the Boston Events Calendar for May 2010 for details.

7.  Have some laughs

Boston's comedy scene is stronger than ever with Boston and Cambridge comedy clubs competing to attract rising local talent and top national/international comics.  Cover charges are usually in the affordable $20 range - leaving you with a few extra dollars in your pocket for dinner in one of Boston's restaurants.

8.  Go on a day trip to Newport

For an easy day trip from Boston, visit Newport, Rhode Island, just 60 miles to the south.  Explore gilded-age mansions along Ocean Drive and Cliff Walk, take a harbor cruise, and have fun shopping and trying all the local restaurants.

Sailboats in Newport's harbor in early evening

9.  Head to the beach on Memorial Day

Enjoy the beach without leaving the city!  Boston beaches may not rival Cape Cod or Martha's Vineyard - but they have lots of charm and convenience, especially when other reasons keep you in the city on the weekend. 

10.  Enjoy a magical evening at the Diana Ross concert

For a memorable evening, join super star Diana Ross for what is sure to be a spectacular performance at the Wang Theatre as she kicks off her summer tour.  Check the Boston Events Calendar for May 2010 for details.