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53 Things To Do This Autumn In Boston: The Ultimate Fall Guide

Vanessa Barron Vanessa Barron

53 Things To Do This Autumn In Boston: The Ultimate Fall Guide

There’s nothing quite like Boston in the fall.

With the leaves changing and the weather dropping in temperature, it’s finally that time of year when we can wear our best fall jackets, sip on pumpkin spice beverages, and munch on apple cider donuts. The fall season is brimming with activities to do in Boston, from sunflower fields to apple picking to fall foliage hikes. Here’s our ultimate bucket list for the best time of the year:

1-5. Wander through vibrant sunflower fields

The best way to say goodbye to summer and hello to autumn is to stop by a sunflower field in full bloom. These flowers will look their best in early to mid September, so it’s the perfect seasonal activity to drive outside the city and have some fun in the gorgeous sunflowers! Our favorite fields include:

  • Verrill Farm – Concord, MA
  • Colby Farm – Newbury, MA
  • Lyman Orchards – Middlefield, CT

6-11. Enjoy a delicious apple cider donut from a local bakery

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
  • Red Apple Farm
  • Kane’s Donuts

12-21. Go apple picking at an 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.

22 – 30. Celebrate Oktoberfest at a local brewery

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

31-35. 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.

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36. 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.

37. 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.

38-46. 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.

47-53. 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.

[featured image: Unsplash / Matt Collamer]

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