Here are some ideas on how to enjoy a Boston Vacation or Boston Staycation in September:
Explore Our Farmers Markets
Our Union Square Food Tour occurs right after 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!
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 Harvard Square Food Tour is a new addition to the calendar and has a lot of cool food diversity! So check the Tour Calendar for something fun going on this week.
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.
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 Far from the Tree 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.
Check out our award winning food and chocolate tours!
Smell the Roses
In Brookline, MA you can 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)
Our favorite place to pick apples is Honey Pot Hill Orchards which is outside of the city.
Try A Lobster Roll
Check out our blog post on the best lobster roll in Boston and hang on to summer!
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.
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.
Check out our award winning food and chocolate tours!
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
- 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 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.
