Here are some ideas on how to enjoy a Boston Vacation or Boston Staycation in October:
Explore Our Autumn Farmers Markets and Try A Pumpkin Food Tour
Love pumpkins? 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! And try our favorite Boston Pumpkin Food Tour route from Cambridge to Somerville.
Get Ready for Halloween with a 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 Chocolate Tour and JP Vegan Chocolate Treats Tour are the perfect way to get ready for Halloween. So check the Tour Calendar for something fun going on this week. You can also head over to Salem, MA for a month-long Halloween celebration in this town that loves witchcraft.
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.
Check out our award winning food and chocolate tours!
Try A Bar Crawl with our Craft Breweries
We love Pumpkin Beer and Pumpkin Cider so much, and they’re popping up 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.
Go Cycling Under the Foliage
We are avid bikers, and Boston has some of the best trails in the state. Some of our favorite places to bike and enjoy nature include:
- The Fens
- Minuteman Bike Path – Somerville to Bedford, MA
- Jamaica Pond
- Boston College/Chestnut Hill Reservoir
- Charles River in Cambridge, MA (Sundays closed to vehicles)
Or if indoor sports are more your speed, check out:
- PKL pickleball bar in South Boston
- Puttshack indoor mini-golf in the Seaport
- BeachHouse indoor volleyball in Natick
Visit Salem if You Dare
Salem, Massachusetts is full of interesing spooky stories and even a Salem Food Tour, but there’s a reason that locals avoid it in October and that’s because it can take over an hour to get there and then it’s hard to park. That said, October is a fun month to explore the city.
Take a Day Trip
We started our Northampton Coffee Shop Food Tour on Saturdays and Northampton Food Tour on Sundays (to be reopened) as a way to promote a fun, foodie daytrip to this college town only 2 hours from Boston. You can easily spend all day there or stay overnight at historic Hotel Northampton. Check out our post on the Top 10 Things to Do in Northampton if you want to make a day of it.
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.
Take a Cooking Class!
Cooking classes are fun year-round, but there’s something special about learning to cook from your autumn farmers market bounty. Butternut squash soups and veggie pizzas are just some of the things you can become quite proficient at. Here’s our Top 20 Cooking Classes in Boston and beyond.
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 October 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.