What To Do in Boston in June

Ahh.. early summer! School’s out, and it’s also time to plant cherry tomatoes! Are you planning a trip to Boston in June? Are you looking for a Boston vacation or staycation in June? Year-round, Massachusetts is a great vacation spot for domestic and international tourists alike. Our city comes alive in the early summer and shows off in every way.
Kendall Square Cocktails

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


Free Outdoor Movies + Concerts


Year after year, we love the free movies at the Hatch Shell (Friday Flicks). On June 21, 2019 they are showing Ralph Breaks the Internet at the Hatch Shell on the Esplanade. The following week, Boston Harbor Hotel is showing Casablanca (and grab a 7:45pm dinner reservation at the Rowes Wharf Sea Grille to get the best seat by the pier!) And while it’s not quite June, the Boston Pops host a special practice concert on July 3rd at 8pm at the Hatch Shell that’s a ton of fun, and you avoid all the crowds!



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! Our Fenway Food Tour is a new addition to the calendar, and we have lots of stories to share about the old ball park and the foodie neighborhood that surrounds it. 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. We love this new tour, full of American Ballpark eats!

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)

Or if indoor cycling is more your speed, try a cool spin class with a live band at Somerville’s The Jungle community space.



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 June 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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