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53 Fabulous Things To Do In Boston This October

Vanessa Barron Vanessa Barron

53 Fabulous Things To Do In Boston This October

Enjoy the best of Boston this October.

As the temperature drops and the leaves change colors, Boston is looking positively picturesque at this time of year. And with Halloween just around the corner, there are tons of activities to take part in around the city this October! From festivals to nature walks, here are our recommendations for plans this month:

1-9. Celebrate Oktoberfest at a local brewery

Dust off your lederhosen—it’s time to celebrate Oktoberfest 2021! While Germany cancelled their celebrations this year, you can still celebrate right here in Boston all throughout October. Oktoberfest typically starts mid-September and traditionally ends on the first Sunday of October, but many local bars extend the season to all throuhgout October. That means right now is the perfect time to enjoy some quality beer and bratwurst at these local breweries and restaurants!

10-19. Go apple picking at a tranquil orchard

Apple picking is the quintessential fall activity in New England. What’s better than exploring picturesque apple orchards, picking your own, and taking a bag home to enjoy in a homemade apple pie or just by themselves? Our list of the ten best orchards will definitely get you motivated to plan a weekend excursion outside the city.

20. Explore Massachusetts’ spookiest town, Salem

Just 17 miles north of Boston, sits the small, quaint town of Salem: a place known for its ghosts, mysterious energy and, of course, its famous witch trials. First established in 1626, Salem began as a simple religious town but hysteria and fear soon took over when hundreds of local people were accused and subsequently condemned for witchcraft. The town has done its fair share of repentance for the harrowing trials, but Salem has since been known as a town rife with magic and witches. From haunted spots and historic sites to magic shops, we’ve come up with a few magical Salem spots to explore and bask in the city’s witchy spirit. Check out our full guide to exploring Salem here.

21. Catch the fall foliage at the best rated spot in Massachusetts


Planning a trip to the countryside to catch the leaves changing colors this fall? Lenox, MA should be on your itinerary. According to Reader’s Digest, this Berkshires town has some of the most vibrant fall foliage in the country. Starting in late September, the area’s landscapes are ablaze with reds, yellows, and greens.

22. Or explore a hidden waterfall in Vermont, surrounded by changing trees

Tucked away in Warren, VT, these falls are the perfect natural spot to escape the leaf-peeping crowds. A wild swimming spot may not sound like the most appealing fall destination, but hear us out. If you’re looking to escape the throngs of leaf-peepers currently exploring the New England wilderness but still want to bask in the glorious fall foliage of the area, this is the place for you this fall.

23-27. Get lost in a corn maze

Before escape rooms were all the rage, corn mazes were (and still are!) the best places to have fun  and solve a massive outdoor puzzle with your friends. Bring family and friends for a day of trial and error as you navigate your way through fields of corn as far as the eye can see at a corn maze close to Boston.

28. Cheer on the Boston Marathon participants

It’s been nearly 30 months since Boston last hosted its famous race, but the Boston Marathon will be finally back on October 11 this year. While things will look much different this year from previous races, it’s still a fun spectacle to cheer on the runners—and maybe recognize a few of your friends or colleagues!

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29-37. Go on a beautifully haunting hike through an abandoned ghost town

A spookier alternative to the classic autumn nature walk is exploring one of Massachusetts’ ghost towns. As our state is home to some of the first settlements in the United States, it’s no surprise that there are plenty of ghost towns around. Whether the original inhabitants abandoned the villages over decades or were forced to leave, there’s plenty of interesting history remaining for you to explore on a hike through ages past.

38-44. Go glamping in the great outdoors

Fall weather can be unpredictable, but you can bet that a glamping experience is sure to be a comfortable getaway in nature this fall.  Glamping (glamorous camping!) provides all the beautiful scenery of the outdoors without sacrificing modern amenities. Luckily there are tons of glampsites around New England. While some require long car rides away from the city, the trek will absolutely be worth it. Check out our top picks for glamping outside of Boston for a lovely fall getaway.

45. Shop for some seriously spooky Halloween costumes

Want to assemble a perfectly spooky Halloween fit? Look no further than your local thrift stores—thrifting is one of the best options to shop for Halloween costumes without breaking the bank, and Boston has no shortage of super-cool thrift shops where you can browse around. Our list of 9 Boston thrift stores includes boutiques and chains of all price ranges and styles, but no matter where you go, you’ll be certain to leave with a Halloween costume that’s completely unique.

46-47. Try out a new restaurant

There’s a plethora of new spots opening in Boston this fall. Our favorites: Coquette, a flirty and fancy coastal-French restaurant, and Bar Enza, an Italian eatery. with a Michelin-star chef. Both of these brand-new spots promise delicious foods in lovely settings that will whisk you away from Boston into a flavorful world of gourmet innovation!

48-53. …or revisit a classic: the Apple Cider Donut 

It’s that time of year when local orchards and bakeries start serving those steaming hot, cinnamon-dusted delicacies we call apple cider donuts. When you’re craving a fresh-baked donut, you don’t have to travel too far to satisfy your cravings. Check out our list of the best places in in the city to get one (or a dozen), including Blackbird Doughnuts, Kane’s Donuts, and Wilson Farm.

[featured image: Unsplash / Mark Olsen]

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