11 Reasons Why Fall in Boston is the Best

Crisp autumn air, bright color-changing leaves, days spent apple picking, fresh-out-of-the-oven apple cider donuts and pumpkin pies – these are a few of a New Englander’s favorite things. When the seasons turn at the end of August and the hoards of summer tourists start to clear out, Boston becomes the most beautiful version of itself. From September through November, the prime place to be is right here in Boston. No other state can compare with our fall traditions and no other place in the world can compete with our seasonal attractions. Get ready for the best three months of the year with IM Boston’s list of 11 reasons why Boston just can’t be beat in the fall.

1. Fall Foliage

Boston in the Fall

I mean, really? Could the Boston Public Gardens BE any prettier?

Thousands of tourists herd to Boston every fall to take in the breathtaking change in foliage unique to New England. The Public Gardens, the Arnold Arboretum of Harvard University and Blue Hills Reservation are some of the best local destinations, but taking a road trip up through New Hampshire, Vermont and Maine will ensure you’ve seen the full leafy spectrum of a New England fall experience.

2. Haunted House Tours 

Boston Haunted House ToursFall is the season to be frightened, and Boston just so happens to be in one of the most haunted areas in the country. You’ve got Spookyworld up in Litchfield, New Hampshire, for all your haunted hayride and creepy house thrills, then there are the Haunted Boston Ghost Tours which bring you by lantern light through the scariest, most ghost-ridden streets and properties the city has to offer.

3. Pumpkin Flavored Everything

Pumpkin Whoopie Pie, Boston

The Pumpkin Whoopie Pie from The Tap Trailhouse in Boston, MA

Of course we Bostonians can’t wait until the air turns crisp and we take those first, refreshing sips of our Dunkin’ Donuts pumpkin iced coffees, but we get even more pumped for the seasonal sweet treats that go along with our iced caffeine. Ridiculous pumpkin bread from Flour, pumpkin beer floats with homemade vanilla ice cream from Saus and creamy autumn pies from Petsi’s galore! The more the merrier.

4. Apple Picking at Local Orchards

Apple picking near Boston

Nothing makes the whole family happier than spending a cool fall day at a rolling apple orchard not too far from home. Just outside of Boston, you’ll find plenty of quintessential New England farms perfect for filling up bags with plump apples while warming up with fresh, hot cider brewed in house. We recommend Lookout Farm in South Natick or Honeypot Hill in Stow for the best pickings and fillings.  

5. Hot Apple Cider Donuts

Apple Cider Donuts, Boston

Photo courtesy of Carpe Season

We’re not sure if anyone else has noticed, but a number of Whole Foods Markets have started rolling out sugary, melt-in-your-mouth mini cider donuts in the front entry as a warm fall welcome for the months to come. You can also find these crave-worthy seasonal delights at most of the area’s apple orchards, or at the city’s very own Boston Public Market where local vendor Red Apple Farm turns out dozens of fresh-baked dough-pillows of perfection right at the front door.  

6. Salem Witch Attractions

Salem witch house near Boston

Salem, Mass has one of the darkest histories in all of America for being the site of dozens of alleged “witch” executions, which you can learn about while walking one of the town’s witch tours. If you’re less of a history buff and more of an adrenaline-junkie, spend your Halloween at one of Salem’s highly-rated haunted happenings.

7. Local Pumpkin Patches

Boston Pumpkin patches

Similar to the joy of apple picking, pumpkin picking elicits a certain nostalgia for us New Englanders. We spent the fall seasons of our childhoods sifting through pumpkin patches for the perfect picks and carving obscure faces and shapes out of them at our kitchen tables. Consider taking a drive out to Smolak Farms in North Andover for their annual Pumpkin Festival and Great Pumpkin day where the whole family can take a hayride over to the pick-your-own patches and partake in other festive activities.

8. Local Brewery Tours and Events

Boston beer tours and events

What better time of year to take a local brewery tour than during the fall when beer companies start spinning out seasonal favorites? Local beer staples, such as Sam Adams and Harpoon, offer frequent brewery tours and host fall events in light of the annual release of best-selling, autumn-inspired flavors. Sam Adams invites Boston to partake in Bostoberfest on September 10th for live music, food and beer pairings and interactive games, while Harpoon’s Octoberfest, in Boston’s South End, will be celebrating with beer, bratwursts and chicken from September 30th through October 1st.  

9. Bonfires

Boston bonfires with friends in the fall

I understand it may be difficult to host or partake in a bonfire when you live directly in the city with no backyard, but if you live in a woodsy area just outside of Boston or have friends in the suburbs, then you know what I’m talking about. I’m talking about cuddling up in your favorite hoodie and a pair of jeans and kicking back with your closest friends around a crackling fire-pit on a crisp October evening. Grab a couple sticks and shove marshmallows on them and you’ve got yourself a Friday night.

10. Football Season

New England Patriots, Tom Brady

We don’t mean to brag (yes we do), but Boston is home to the luckiest fanbase in the country. The New England Patriots are without a doubt one of the greatest football teams in the NFL and we aren’t afraid to remind you about it. Every year after Tom Brady adds another ring to his collection, we wait with empty voids in our hearts until football season starts up again in the fall.

11. The Weather

Boston Fall Weather

Absolutely nothing beats New England weather in the fall. Not your steady “west coast best coast” summer heat or your sticky Florida humidity. We like to cozy up in oversized sweaters and scarves on brisk October days and we enjoy rolling the window down and feeling that fresh November air. It brings us back to the days we ran outside and dove into the crunchy leaf piles dad tried to rake up and when our cheeks would turn cherry red from playing tag during recess. Fall is Boston’s time to reflect and rejuvenate and we like to soak up the nice weather as much as we can before January smites us with single digit weather predictions and double digit snow forecasts.


Did you like this post? Follow @IM_Bost on Instagram and like us on Facebook for all things Boston!



Review overview