What To Do in Boston in May

It's gonna be May! Are you planning a trip to Boston in May? Are you looking for a Boston vacation or staycation in May? Year-round, Massachusetts is a great vacation spot for domestic and international tourists alike. Crocuses have blossomed, forsythia are sprawling, and graduation season is in our midst!

Here are some ideas on how to enjoy a Boston Vacation in May:

What To Do in Boston in May


The Boston Calling Music Festival in Harvard Square


LA may have Coachella and Chicago has Lollapalooza, but Boston has a new claim to fame: the Boston Calling Music Festival. This year the Festival is May 27-29, 2022. Take a Harvard Square Food Tour or Chocolate Tour that weekend in nearby Harvard Square. NIN, Metallica, Avril Lavigne, Paris Jackson, and more await!



Take a Food Tour or Chocolate Tour with Off The Beaten Path Food Tours


We run our Food Tours and Chocolate Tours year-round and our friendly guides can’t want to meet you! Central Square Food and Mural Arts Tour is running Sundays. So check the Tour Calendar for something fun going on this week.



Go Farmers Market Hopping!


Farmers Markets are back in season, woohoo! In all of the neighborhoods that we tour, there is a local farmers market. Check out this aggregator to find the Massachusetts Farmers Market near you!



Cheer on the Red Sox and sit near the Lone Red Seat!


Food and sports go hand in hand, we think you’ll agree. Our newest food tour is the Fenway Food Tour which explores the best and most iconic eats in this historical neighborhood that’s now a foodie hotspot. Be on the list to find out when our latest tour launches. Check out our post of our Favorite Boston Sports Bars, and catch the game after one of our tours this weekend.



Smell the Roses


In Brookline, MA you can rent a Bird electric scooter and scoot your way around the city. You can also rent an electric bicycle to help you up the hills in nearby Somerville. Some of our favorite places to walk around and enjoy nature include:

  • The Fens
  • Minuteman Bike Path – Somerville to Bedford, MA
  • Jamaica Pond
  • Boston College/Chestnut Hill Reservoir
  • Fresh Pond in Cambridge, MA
  • Charles River in Cambridge, MA (Sundays closed to vehicles)



Try A Bar Crawl with our Craft Breweries


Check out our blog post about our favorite craft breweries in Boston. There’s so much creativity in the Boston brew scene, from the label to the process/recipes to the names of the local bottles, these are truly labors of love. On our tours we often sample beer, and you can email us for specific recommendations if you want more recommendations.



Make It a Bubble Tea Date


Check out our list of our Favorite Bubble Tea in Boston. From avocado shakes to unique frozen creations, you won’t want to miss these fun and inventive spots.



Enjoy Music or Theater


Lift your spirits with a performance that wows. There are so many awesome music venues in Boston, from outdoor to indoor beats! Check out our list of our favorite music venues in Boston.



Plan a Bachelor or Bachelorette Party: A Food or Chocolate Tour!


It’s “wedding season” and our Food Tours and Chocolate Tours make perfect bachelor or bachelorette parties. We’ll create some special surprises at each stop. Contact us to find out more.



The Usual: Art Galleries, Restaurants, Historical Sites are all open


Check out some of our other recs of things to do in Boston like this blog post on Off The Beaten Path Things To Do in Boston. Enjoy our city and explore all of its off the beaten path finds.


Our Food Tours and Chocolate Tours of interesting Boston neighborhoods are a can’t-miss May activity in Boston. So whether you’re a local or tourist, start practicing saying “wicked cool” and check our Tour Calendar for what’s going on this week.

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