What To Do in Boston in September

Missing summer already? Not to worry, we have a full list of exciting things to do around Boston this month that you won't want to miss!
boston september things to do

Here are some ideas on how to enjoy a Boston Vacation or Boston Staycation in September:
What To Do in Boston in September

1

Explore Our Farmers Markets

 

Our Roslindale Village Boston Food Tour includes a trip to the best Farmer’s Market in the city. 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!

 

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! 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.

 

3

Late Night Desserts in Boston

 

Dessert warms your soul so as the cooler weather moves in, time to seek out that molten lava chocolate cake or Boston cream pie. Our Chocolate Tours are a perfect adventure or check out our Most Indulgent Desserts in Boston.

 

4

Try A Bar Crawl with our Craft Breweries

 

We love Pumpkin Beer and Pumpkin Cider so much, and they’re popping up as early as this Fall at places like Cambridge Brewing Company and Bantam Cider. 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.

 

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)

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

 

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

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 Fenway Food Tour 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.

 

8

Enjoy Music or Theater including Live Shows and Movies

 

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

 

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 Boston Food Tours and Chocolate Tours of interesting Boston neighborhoods are a can’t-miss September 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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