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Harvard Yard fall foliage
Photograph: Courtesy GBCVB/Kyle KleinHarvard Yard fall foliage

15 ways to have an amazing fall in Boston

How to have an amazing fall in Boston. Everything from pumpkin picking to apple picking to fall foliage are on the menu!

JQ Louise
Edited by
JQ Louise
Written by
Megan Johnson
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There’s not much like fall in Boston. The stunning foliage in our exquisite outdoor spaces, the feeling of drinking a hot apple cider as you stroll Newbury or the sight of a moving van crunched up like an accordion on Storrow Drive. Along with cooler temps, it’s our season of celebration between the hot summer and frigid winter, when you can get outside and really enjoy the best of the city and its surroundings. Whether you’re looking for a seasonal activity like apple picking near Boston or something cozier like a nice cup of Boston’s best hot chocolate, here are the top things to do to make the most of our best season. 

RECOMMENDED: Full list of the best things to do in Boston

Time Out Market Boston
  • Restaurants
  • Fenway/Kenmore

Like some variety when you go out to eat? Time Out Market Boston has you covered. Boston's first contemporary culinary hub boasts a tantalizing variety of curated food offerings, two top-notch bars and lots more. There is plenty of seating—both indoors and on a roomy, sun-splashed patio—and some of the biggest culinary names in Boston are delivering a varied assortment of delicious dishes and 'Gram-worthy bites.

How to have an amazing fall

  • Things to do

Each fall, Boston and much of New England come alive with blazes of yellow, orange and red. Leaf-peepers descend upon the area, hoping to catch a glance of the season in its full glory. Whether you stick close to home or travel further afield, get out there and see the best of the changing colors around the region.

  • Things to do
  • Walks and tours

Get out on the water before it gets too cold. If you've been putting off going on a whale watch, now is the time—prime whale watching season is March to November. There are plenty of whale watching cruises departing from Boston and surrounding harbors, and all make a beeline for Stellwagen Bank, one of the best spots for whale watching in the world.

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3. Ride a BlueBike

Love to ride bikes but don’t want to go near main roads? Head to Piers Park, the stunning waterfront park in East Boston. After you check out the views of the city, grab a BlueBike at the park’s entrance and follow the bike path along the Mary Ellen Welch Greenway. It brings you outside the Maverick Square area, through Bremen Street Park, and winds through Logan International Airport territory. The rabbit-filled stretch, which features the Blue Line zooming by you, ultimately leads to Constitution Beach in Orient Heights. There, you can dock your bikes and watch the planes take off from the sand. 

  • Travel

It doesn't get much better than food and travel—why not combine the two and take a food-focused road trip? There are several easy road trips to take in some of the best bites in the region. Given New England's relatively small footprint, you can mix and match these culinary stops based on your liking.

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  • Museums
  • Art and design

The deCordova Sculpture Park & Museum lures art lovers year-round to its 30-acre spread in leafy Lincoln. The only park of its kind in England, it’s the perfect place to get some fresh fall air while checking out world-class art. 

  • Travel

Taking a hike is one of the best ways to catch some autumn vibes. Serious local hikers may head farther afield to the White Mountains or the Appalachian Trail, but when you just need a little bit of nature, there are plenty of worthy hikes near Boston that are easy to get to, whether it’s climbing a lung-busting hill or exploring trails through scenic wooded preserves. If you’re a non-driver, portions of the Middlesex Fells Reservation and Blue Hills Reservation are reachable by T or bus. 

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  • Things to do

Apple picking is one of the quintessential autumn activities in New England. Fresh, crisp apples in multiple varieties taste even better when you pick them yourself. Head to these farms within an easy drive of Boston to pick apples, sip hot apple cider, and get your fill of fresh cider donuts. Check out our guide to the best local apple-picking near Boston

8. Hit Up a Fall Fair

New England is chock-full of autumn festivals and fairs. From tiny town festivals to large-scale events that draw guests from far and wide, these harvest celebrations embrace the season in New England. Feast on oddly-decadent treats at The Big E (it goes far beyond fried Oreos) or hit a classic harvest activity like oxen pulling at the Topsfield Fair. 

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  • Things to do

While the city boasts plenty of great restaurants with outdoor seating, there's something wonderfully old school about going on a picnic. The best part? You don't need a reservation—just grab a blanket, pack up some food or order takeout and find your way to one of the most peaceful picnic spots in Boston. The Boston Public Garden is always a popular pick, but you can find other stunning spots for sitting down with a snack at Belle Isle Marsh Reservation, Franklin Park, or Jamaica Pond.

Explore a new neighborhood
Photograph: Shutterstock

10. Explore a new neighborhood

There is so much more to Boston than Newbury Street. Open up Google Maps and take a look at a neighborhood you’ve never visited. From historic buildings to delicious local cuisine, chances are you can find an interesting space you’ve never explored. 

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  • Travel

Sometimes the best part of living in Boston is leaving it.  A cabin in the woods is the perfect place to recharge. Round up some friends for a weekend getaway filled with outdoor adventure or just take your sweetie to the middle of nowhere for a romantic retreat. Rustic charm and easy access to outdoor adventures abound, and there’s always the urban jungle awaiting you when you return.

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  • Attractions
  • Parks and gardens
  • Jamaica Plain

It’s so much more than just a park. This living collection of thousands of trees, shrubs, and woody vines is recognized as one of the most comprehensive and best documented of its kind in the world. If you've seen the Arboretum in summer, take an autumn stroll to see the seasonal changes.

  • Travel

No sitting on the Sagamore Bridge in bumper-to-bumper traffic? We’ll take it. Everyone heads to the Cape and the Islands in the summer, but they’re also a tremendous getaway in the fall. Grab a beachfront hotel room at an off-season price, or take a tour of a cranberry bog.

Rediscover Boston this fall

  • Restaurants

As summer nears its end, take advantage of the amazing outdoor dining available across the city right now. Savor summer’s bounty at seafood spots or swing by one of the best people-watching perches on the street patios in the North End. Enjoy the sunny days, balmy nights and refreshing sea breezes while the last few weeks of summer roll on in Boston. If you are coming back from a month down the Cape, there has never been a better time to rediscover our city at the best restaurants in Boston.

RECOMMENDED: Guide to Boston's Michelin-worthy restaurants

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  • Restaurants
  • Coffee shops

Nothing warms you up faster than a strong cuppa joe in the winter, or cools you down faster in the summer than a classic, iced coffee (and the true New Englander may argue that the latter kind of coffee is popular in Boston all year round). Though prolific coffee chains (we’re looking at you, Dunks) ensure that you’re never too far from satiating your caffeine craving, there are a number of Boston coffee shops and cafes worth seeking out for a change of scenery. Here are some of our favorite places to grab the best coffee in Boston. And if you take your java with food, be sure to check out the best donut shops, best breakfast spots or brunch spots in Boston.

RECOMMENDED: Full guide to the best restaurants in Boston

  • Things to do

During spring and fall, Boston has about the most perfect weather on the planet. But the long hot days of summer, rainy days and brutal winters drive even the most hearty New Englander inside sometimes. When you’ve run through Netflix and HBO Max and really need to get out of the house, there’s plenty of galleries, museums, historic landmarks and more to keep you occupied. Here, find our top activities for crummy days in Boston. Then, when the weather improves, take one of the best walking tours in Boston or hit up one of Boston’s best parks.

RECOMMENDED: Full guide to the best things to do in Boston

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  • Bars

We got together with Jameson Irish whiskey, Ireland’s most famous distiller, to help round up some of our favorite bars to sip on a glass of the best brown stuff. From live music at Druid to indoor food trucks at Coppersmith, we're pretty sure you’ll have the type of night where strangers become friends, and friends become family.

And if you don't feel like barhopping, click here to get a bottle of Jameson Irish Whiskey delivered to your doorstep. 

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  • Bars

When nice weather finally arrives, there’s no better way to spend a sunny afternoon than clutching a cold glass beneath an umbrella in a beer garden in Boston—it’s one of our favorite things to do in summer. Many of these outdoor drinking locales are known for their scenic patio bars, with some set up in taproom parking lots or on rooftops. Once you've snagged a table (you may need to make a reservation), you can order tasty treats to enjoy while you sip beer from top local breweries. (And during normal times, check out the best craft beer bars in Boston to knock hard-to-find brews off your sudsy bucket list.) Find a comfortable spot and settle in for the evening with our guide to the best beer gardens in Boston.

RECOMMENDED: Full guide to food and drink in Boston

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  • Travel

Apartment living is a beautiful thing, but sometimes, even the most committed of downtown-dwellers need stretch their legs by getting outside and hiking near Boston. Dedicated adventurers may travel all the way to the White Mountains or the Appalachian Trail to get their nature fix, but there are plenty of picturesque hiking spots near Boston that will do the trick for us recreational trekers. Whether it’s climbing scenic wooded preserves or exploring waterfront trails, these local hikes are perfect for walking off the chaos of The Hub. No time to leave the city limits? Try one of Boston’s best parks. Looking to get away for a bit longer? Check out the best weekend getaways from Boston and the best day trips from Boston.

RECOMMENDED: Best things to do in Boston

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