Fall in Massachusetts: 12 Must-Visit Destinations & Fall Fun Ideas


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Looking for where to go to check out Massachusetts’ fall foliage? Look no further! This list of 12 must-visit spots for fall in Massachusetts will lead you to the best leaf peeping and fall fun in the Bay State. In addition to stunning scenery, this New England state offers a wide world of fall fun for both residents and visitors alike.

With plenty of hiking options, scenic drives, wholesome family fall fun activities, and a town that is sure to get you in the Halloween spirit, fall in Massachusetts is where it’s at!

When to Visit Massachusetts for Fall Colors

Massachusetts typically sees peak fall foliage in the first couple of weeks of October, but check out the Weather Channel’s fall foliage map for real-time tracking. The Bay State has plenty to do and see all year round, but come fall the landscape becomes an even more spectacular setting for your adventures in Massachusetts.

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Fall in Massachusetts: Where to Go

Monument Mountain

Fall foliage in Massachusetts stretches out under a setting sun
Look at these gorgeous MA fall views!

Located in Great Barrington, a town in the Berkshires that Vogue once described as “quietly cool,” Monument Mountain offers scenic views from its 1,624-foot summit that allow you to look out across the Housatonic River Valley, with the Catskills of New York in the distance.

Monument Mountain has a storied place in literary history as well, as it is said that literary greats Herman Melville and Nathaniel Hawthorne climbed the summit together before having to shelter in a cave due to rough weather, during which the inspiration for Moby Dick was born.

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Lower Berkshires Waterfalls

Bash Bish Falls in Massachusetts is surrounded by fall foliage
Massachusetts fall colors and a waterfall? Yes please!

There are plenty of waterfalls with gorgeous fall foliage backdrops to choose from in the Bay State, but Campbell Falls, Race Brook Falls, and Bash Bish Falls are all within easy driving distance of one another in the picturesque towns of New Marlborough, Sheffield, and Mount Washington, respectively, and are well worth adding to the list of the best places to visit in Massachusetts in the fall!

With multiple falls that vary in length between 50 and 100 feet, the hikes out to these waterfalls are all considered moderate but it is said that if you approach Bash Bish Falls from the Massachusetts side, it is a much steeper and more advanced hike than approaching from the New York side. Bash Bish Falls is the highest single-drop waterfall in the entire state and a regional favorite, which is probably why it was added to this list of the top 50 Things to Do in Massachusetts.

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Pleasant Valley Sanctuary

Fall trees in the Berkshire Mountains
Fall foliage in Massachusetts is absolutely gorgeous.

Situated in the adorable town of Lenox, Pleasant Valley Sanctuary is comprised of over a 1,000-feet of protected land and wildlife sanctuary nestled at the base of Lenox Mountain. There are multiple hiking trails to choose from as you make your way through the blazing orange, ruddy crimson, and burnished gold of the autumn leaves.

Lenox is also home to some pretty cool places to visit, like Tanglewood, the iconic music venue that serves as a summer performance space for the Boston Symphony Orchestra, and The Mount, the breathtaking estate of early 20th-century author Edith Wharton.

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The Mohawk Trail

A hairpin turn on a fall foliage road in the Berkshires
Beautiful Berkshires fall foliage on the Mohawk Trail

The Mohawk Trail is a historic route (with alternative routes, too!) that leads through the scenic northern Berkshires, which are absolutely bursting with fall color during prime leaf peeping season.  It winds through picturesque New England towns that offer lots of lovely side trip ideas, like the Bridge of Flowers in Shelburne Falls, an old trolley bridge that was reimagined as a walkthrough flower garden, and for the more adventurous,  Zoar Outdoor Ziplining in Charlemont lets you take in the MA fall foliage from an entirely different vantage point as you soar through the canopy of trees. 

MA’s Mohawk Trail is one of the oldest scenic routes in the country and is a beautiful drive all year round, but if you can do it while the trees transform into a vivid palette of gold and burnt orange with dashes of crimson, you should. Don’t worry, there are scenic overlook spots along this route to hop out and take advantage of the plethora of photo opportunities!

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Mount Sugarloaf State Reservation

A river in Massachusetts is lined with fall foliage at sunset
Fall in Massachusetts is just as scenic as scenic can be

You can drive or hike up to the lookout tower of Mount Sugarloaf State Reservation, but the visual reward will be the same either way: Sweeping views of the Connecticut River and Pioneer Valley below and the Berkshires in the distance. Looking across the valley, you see the quintessential New England aesthetic with farmland, river, and you might even catch a glimpse of a beautiful white steeple in the village below. As the leaves turn color, the views here go from lovely to absolutely stunning! Quick heads up: the road to drive up is reported to be fairly narrow, so if you’re driving an extra-wide vehicle, it’s probably best to park and hike up.

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Maudslay State Park

A woman smiles as she enjoys fall foliage in Massachusetts at a park
Massachusetts fall

Positioned on the Merrimack River in the cute coastal community of Newburyport, Maudslay State Park is a historic fixture in Newburyport as a former private estate that has since been adopted by the state, providing visitors with access to miles of easy to travel trails, old stone bridges, and even a 19th-century garden! As the season shifts from summer to autumn, the blazing fall foliage is reflected in the Merrimack River, with an easy to follow trail that meanders alongside. The town of Newburyport is also less than an hour from other must-visit locations like Salem, Rockport, and Marblehead, so be sure to take advantage of its location to check out these other coastal gems!

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Mount Greylock State Reservation

A tall memorial tower sits at the top of Mount Greylock in Massachusetts
Editorial credit: Keith J Finks / Shutterstock.com; hiking to the top of Mount Greylock is a fun fall Massachusetts activity

Located in the picturesque town of Adams, the summit of Mount Greylock is 3,491 feet and the highest point in Massachusetts. You can drive or hike to the top, and on a clear day you can see up to 90 miles away, catching parts of 4 states and 5 mountain ranges, and the fall foliage views go on and on and on. Atop Mount Greylock is an impressive 92-foot tall granite Veterans War Memorial lookout tower and Bascom Lodge, providing meals and lodging for travelers looking to stay overnight on the mount. Be aware that the temperature drops significantly as you near the summit, so be sure to dress accordingly! Road access to Mount Greylock is closed on November 1, so don’t wait too long to catch the incredible autumn views atop the summit of this gorgeous natural wonder.

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Salem MA

The Salem Witch House is seen with pumpkins in front for fall
Nothing quite like a visit to Salem to get a person in the mood for Halloween fun!

The perfect Massachusetts town to visit in October, Salem is full of fun things to see and do to kick off your fall fun! Not only will you find ghost tours, haunted places, great restaurants, and cool places to stay, but the fall colors in Salem MA aren’t half bad, either.

In fact, Salem is full of fun FREE things to do, too, including taking yourself on a little tour of all the sites where Hocus Pocus was filmed.

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Fall in Massachusetts: What to Do

Go Apple Picking

Someone is reaching up to pick apples off a tree
Apple picking is the perfect fall fun activity

There are several great pick your own apple orchards across the Bay State, and is there anything more quaint and wholesome than heading out on an early fall day to pick your own apples?

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Visit a Cranberry Bog

Crimson red cranberries float on the top of cranberry bogs in Massachusetts
Editorial credit: Heidi Besen / Shutterstock.com; cranberry bogs during harvest season are pretty neat looking!

One of Massachusetts’ claims to fame is their cranberry bogs, and fall is harvest time! Harvesting cranberries is an interesting process where the cranberry fields are flooded so the fruit can float to the top, making it easier for the machinery to harvest them. Some cranberry bogs will even let you strap on a pair of chest waders and hop in the bog to help, like Benson’s Pond in Middleboro!

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Play at a Pumpkin Patch

Two little girls carrying a pumpkin through a pumpkin patch
Just good, wholesome pumpkin patch fun!

Of course, pumpkin patches are just good, old-fashioned fall fun! There are several great pumpkin patches in Massachusetts that offer great family activities like hay rides and petting zoos, so if you’re looking for fun family things to do in MA, consider heading to the nearest pumpkin patch.

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Get Lost in a Corn Maze

Empty path through a corn maze
Definitely a great fall family fun activity.

Just about the only time “getting lost” is fun, corn mazes are another one of those simple fall activities that deliver big on fun, and there are plenty of them in Massachusetts to choose from. Sometimes you’ll even stumble across a corn maze offering quintessential fall in MA staples like cider donuts… yum!

Massachusetts in the fall should be on any leaf peeper’s list!

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