otbp logo
Off the Beaten Path Food Tours logo.
  • Home
  • ABOUT
    • About Us
    • CONTACT
    • Where to Meet
    • FAQs
    • Work With Us
  • Tours
    • Cambridge Food Tours
      • CENTRAL SQUARE FOOD AND MURAL ARTS TOUR
      • HARVARD SQUARE CHOCOLATE TOUR
      • HARVARD SQUARE FOOD TOUR
      • KENDALL SQUARE PROGRESSIVE DINNERS
    • Somerville Food Tours
      • UNION SQUARE FOOD TOUR
    • Boston Food Tours
      • ​JAMAICA PLAIN VEGAN CHOCOLATE TOUR – OPENING SOON
    • Private Boston Tours
    • Local Boston Trivia
  • GIFT CARDS
  • Reviews
  • BLOG
Menu
  • Home
  • ABOUT
    • About Us
    • CONTACT
    • Where to Meet
    • FAQs
    • Work With Us
  • Tours
    • Cambridge Food Tours
      • CENTRAL SQUARE FOOD AND MURAL ARTS TOUR
      • HARVARD SQUARE CHOCOLATE TOUR
      • HARVARD SQUARE FOOD TOUR
      • KENDALL SQUARE PROGRESSIVE DINNERS
    • Somerville Food Tours
      • UNION SQUARE FOOD TOUR
    • Boston Food Tours
      • ​JAMAICA PLAIN VEGAN CHOCOLATE TOUR – OPENING SOON
    • Private Boston Tours
    • Local Boston Trivia
  • GIFT CARDS
  • Reviews
  • BLOG
A red background with white calendar icon.
A red background with a white ticket icon that surrounded by the text Book Now!

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

1

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!

 

2

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.

 

3

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!

 

14

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.

 

5

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)

 

6

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.

 

7

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.

 

8

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.

 

9

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.

 

10

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

  • Take photos in all of our most instagrammable places in Boston!

 

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.

Related Posts:

  • Best Boston Meal Kits in Boston During Coronavirus Covid…
  • The Top Greek Food in Boston
  • The Most Romantic Restaurants for Boston Dates
  • Fun Mother's Day Activities in Boston
  • A Local Thanksgiving! Boston Restaurant Takeout Guide for…
  • The 5 Best Natural Health Herbal Apothecary Stores in Boston
  • Neighborhood: Boston
  • Category: Things To Do

Share this post:

If you like this post, you'll love

A bowl of vanilla ice cream with multicolor sprinkles.

The Best Ice Cream in Massachusetts

Boston Bachelorette Party Ideas

What To Do in Boston in August

Go back to
the blog Home
Check tour
calendar
Search
browse the blog
Browse by category
Also See...
Related Posts:
  • Best Boston Meal Kits in Boston During Coronavirus Covid Days
    Best Boston Meal Kits in Boston During Coronavirus Covid…
  • The Top Greek Food in Boston
    The Top Greek Food in Boston
  • The Most Romantic Restaurants for Boston Dates
    The Most Romantic Restaurants for Boston Dates
  • Fun Mother's Day Activities in Boston
    Fun Mother's Day Activities in Boston
  • A Local Thanksgiving! Boston Restaurant Takeout Guide for 2022
    A Local Thanksgiving! Boston Restaurant Takeout Guide for…
Book a Tour
Wanna Go Off The Beaten Path?
If you’ve been craving a little adventure, you’re in luck. Fill out the form below to get FREE instant access to our hand-picked list of local stops and hits of flavor for your next stroll around Beantown.

By filling out the form above, you’ll also get our occasional updates and marketing emails.

SEARCH:
  • Home
  • About
  • Tours
  • Gift Cards
  • Get Tickets
  • FAQ
  • Blog
  • Where to Meet
  • Work With Us
Facebook-f Twitter Instagram Youtube Tripadvisor Envelope
Tripadvisor-certificate-of-excellence-2-odv4uk30pacrub03ng4ls5trsqamyk6tdamu93xo8w (1)
Boston-Convetion-and-Visitors-Bureau-2-odv4x9u8g22ldr23smdszh5pkswt72yweqhc5vwq9s (1)
Scouts-Honored-Best-Local-Tour-Badge-odv4w1ntiue482u9ylac8ab1noyk5b3ikntilvq8e8 (1)

Copyright © 2023 Off the Beaten Path Food Tours | Waiver | Terms & Conditions | Privacy

Headquarters: Somerville MA, 02144; Cambridge, MA 02138; Jamaica Plain, Boston, MA 02130

TOUR
CALENDAR

BOOK
NOW!

ALL
TOURS