18 Things to Do in Massachusetts in Fall: Foliage, Festivals & Day Trips

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Massachusetts is one of the most popular destinations in New England during the fall season.

Fall starts in mid-to-late September and this is when the temperature starts to become cooler, ranging between 50°F and 70°F.

You can enjoy many activities in Massachusetts in fall like touring historical sites or taking a scenic drive through the Berkshires to see the stunning fall foliage.

It’s also a time to have fun and join in the many festivals and events like the North Adam’s Fall Foliage Parade or the Salem Haunted Happenings.

If you’re looking to visit Massachusetts in the fall season, this guide has a list of activities and events you can check out along with a foliage map to help you track the best fall foliage in the state.

Would like to see more than just Massachusetts but not sure if it is possible? Check out our one week fall road trip itinerary.

Massachusetts in Fall

Boston in the Fall

During the fall season, tourists and locals alike can enjoy Boston’s autumn foliage, which typically begins in late September and lasts until early November.

And this makes the perfect time to also experience fall activities in Boston which we’ll explore in the following list.

You may find our guide to where to stay in Boston helpful if it’s your first time visiting and want to spend a night or two.

The Esplanade

If you’d like to view some amazing fall colors without ever leaving the city, the place to visit is certainly the Esplanade.

The Esplanade is part of Boston’s Back Bay neighborhood; it runs the length of the Charles River and features lots of tree species, wildlife, and vital green space.

This famous spot in Boston provides city locals and travelers alike a place to stroll among majestic trees in the fall while bundled up against the river’s chill breeze.

Walk as much or as little of the Esplanade as you’d like, but make sure you stop by Owl’s Nest by Night Shift Brewing.

Have a fresh beer and enjoy all the green space the Esplanade has to offer.

View of the sunset sky and water from Storrow Lagoon in Charles River Esplanade, Massachusetts

Arnold Arboretum

If the busier, city-centric aspects of the Esplanade don’t appeal to you for your fall foliage viewing experience, make sure to visit the Arnold Arboretum (125 Arborway).

This living museum features 281 acres of varied landscape and over 15,000 unique plants.

The arboretum is open daily and is always free, which makes it perfect for absolutely anybody to pay a visit.

Owned and operated by the incomparable Harvard University, the arboretum is a place to discover and learn.

Whether you’re in for a nature lesson or not, the arboretum is a lovely place to do fall activities in Boston.

Plus, you might not expect it, but the arboretum is one of the best places in Massachusetts for fall foliage.

The Arnold Arboretum is also featured in our guide to free things to do in Boston.

Head of the Charles Regatta

One of the best Massachusetts fall activities is the Head of the Charles Regatta.

Every year at the end of October since 1965, thousands of rowers from across the nation (and the globe) converge in Boston to race down the Charles River.

Head to the Eliot Bridge Enclosure for amazing views and a more relaxed atmosphere.

If you’re looking for more excitement (and great local food), make your way to the Weld Exhibition- you might even meet some of the star rowers!

This event transforms the city for an entire weekend and makes for a fun fall activity in Boston for the whole family.

Photo of woman rowing in a river

Salem, Massachusetts in the Fall

For one of the best places to visit in Massachusetts in the fall, you’ll have to visit Salem.

Salem is best known as the site of the Salem Witch Trials, and every fall, the city comes alive with spooky tours and Halloween events worth seeing.

To complete your adventure, you can stay at one of Salem’s hotels, inns, and B&Bs.

Take a Walking Tour to Learn Salem’s History

As soon as you enter the city of Salem, Massachusetts in the fall, you can feel a deep sense of its haunted history.

Instead of just feeling the haunted energy, go on a haunted walking tour that will take you to some of the most haunted attractions in Salem like the Old Burying Point Cemetery and the Witch House.

This is a nice way to experience Salem in the fall especially if you’re a first-timer.

Haunt and History Guided Night Tour

Want to see more haunted places in Salem with a local guide?

Take a guided night tour and check out Salem’s beautiful and historic downtown while making stops at some of its known haunted spots like the Old Salem Jail, cemeteries, the Witch Trials Memorial (24 Liberty St), and more.

You can also learn more about Salem’s rich and dark history on this tour.

Self-Guided Ghost Tour

If you find it too spooky to explore Salem at night, go on a self-guided ghost tour during the day.

With your phone, take a stroll among the streets of downtown Salem while you listen to the gripping ghost stories behind them.

This tour is ideal if you want something more self-paced or just want to discover more about the town’s history and other interesting locations on your own.

Plus, taking some of these haunted tours will definitely let you make the most of your time in one of the best towns to visit in the fall in Massachusetts.

View of Salem's buildings from the waters

Salem Witch House and Museum

If you’d rather strike out on your own, the two best places to start are at the Salem Witch House (310 1/2 Essex St) and the Salem Witch Museum (19 1/2 Washington Square North).

The Salem Witch House was the home of Judge Jonathan Corwin and is the only remaining structure you can visit that has direct ties to the Salem Witch Trials of 1692.

You can enter for a small fee and explore historical artifacts that paint a robust picture of the life and times of colonial America.

Similarly, the Salem Witch Museum gives you a detailed account of the fateful events of 1692 as it truly puts you in the time and place so that you start to understand the motivations behind the trials.

Looking for other things to do in Salem? Visit this guide.

Three roofed, black Witch House aka Corwin House in Salem

Berkshire Fall Foliage

The Berkshires, located in Western Massachusetts, are known for their rolling mountain views, crystal clear lakes, and some of the best fall foliage in Massachusetts.

You can also find many hotels in the Berkshires as the base of your fall adventures.

Jacob’s Ladder Scenic Byway

There are so many ways to experience the beauty of the Berkshires in fall, but Jacob’s Ladder features some of the best foliage in Massachusetts.

The two best ways to take in the views: take a scenic drive through the mountains or head out on a hike.

Jacob’s Ladder Scenic Byway is an amazing 35-mile drive and an iconic New England fall foliage drive.

Travel along U.S. Route 20 from Lee, MA, to Russel, MA, and take in the amazing fall views.

Don’t forget to add some of these landmarks as quick stops to your travels: the Becket Land Trust Quarry, the Keystone Arch Bridges, and Jacob’s Pillow!

Stoney Ledge via Haley Farm Trail

If you’re willing to hike for 3 hours or less, you’ll be rewarded with possibly the best panoramic view in all of Massachusetts.

The Berkshires, Massachusetts fall foliage is top-notch on Stoney Ledge, so you’ll have to check it out this season!

Hiking Stoney Ledge by way of the Haley Farm Trail will take you up almost 1,500 feet of elevation gain and through 5.6 miles of trails.

At the scenic vista on Stoney Ledge itself, you’ll be so glad you made the journey.

Plus, this trail takes you back to where you started along a super popular trail along the bowl-shaped Hopper.

This makes it one of the best fall things to do in Massachusetts you can’t miss.

You may also like our guide to things to do in Western Mass.

Scenic mountain views with trees and farmlands in Williamstown, MA

Cape Cod, Massachusetts in the Fall

While Cape Cod is not at the top of your mind when it comes to autumn in Massachusetts, it’s actually one of the nicest places to visit in Massachusetts in fall.

Check out the list for some activities you can enjoy during this season.

Eat Oysters at Wellfleet

Wellfleet Oysters are considered some of the best you’ll ever have- they have a unique flavor that is salty and briny with a hint of sweetness.

And the best time to get them is during the oyster season, which begins in October.

During the fall, you can also experience the Wellfleet OysterFest, which highlights Wellfleet’s oyster industry and features live music, oyster-shucking competitions, cooking demonstrations, and products from local vendors.

Walk Along Cape Cod Beaches

Fall in Cape Cod is a great time to enjoy the beaches without running into too many people.

Unlike the busy summer months, beaches in Cape Cod especially in November have fewer crowds and the weather is pleasant enough for beach activities like picnics or a leisurely stroll.

You can visit beaches like Marconi Beach in Wellfleet or Race Point Beach in Provincetown.

If you’re leaning towards exploring Provincetown, our guide to things to do in Provincetown can help you plan your visit.

Race Point Beach in Provincetown MA

Nantucket in Fall

The island of Nantucket may be small but is a lovely place to be in during the fall- where you can find fun things to do like the ones listed below.

We also featured Nantucket for its beach in our guide to the best beaches in Massachusetts.

Scallop Season

Large sea scallops are technically in-season all year round, but there is a special (more delicious) variety of scallops that are harvested only in late fall.

The Nantucket bay scallops are harvested commercially in November and are quickly added to local menus.

If your family doesn’t mind getting a little muddy, there’s a fantastic tradition that takes place every October.

“Family scalloping” is an opportunity for you to take out the little ones to hunt for Nantucket bay scallops.

You can fill a basket with your family and take them home to boil, steam, or sauté yourselves!

If you prefer a more restaurant-style bay scallop, you can expect them to be added with tons of garlic and butter to freshly made pasta or wrapped in bacon.

Cranberry Festival

There is no better way to celebrate fall in Nantucket than by attending the annual Cranberry Festival at the Milestone Cranberry Bog (Milestone Rd).

The official events have changed slightly in recent years, but what has stayed consistent is the ringing in of the traditional Cranberry Harvest throughout the month of October.

From sustainable markets to guided tours, puppet shows for the little ones, and tons of cranberry treats, visiting the Cranberry Festival is an unforgettable event in the fall in Massachusetts.

Massachusetts Fall Festivals

The following list explores events and festivals held during the fall in Massachusetts.

Salem Haunted Happenings

The Salem Haunted Happenings is a fun fall activity in Massachusetts to get you into the Holloween spirit.

You’ll get to see family-friendly magic shows, costume balls, psychic readings, haunted harbor cruises, ghost tours, live music, spooky theater performances, and more at this month-long event held every October.

Black and white image of Witches brooms in Salem shop

Fall Foliage Parade, North Adams

The Fall Foliage Parade at downtown North Adams is a great opportunity to see some of the beloved autumn events in the Berkshires.

Visitors can enjoy the parade every first Sunday of October and it has been held every year since 1955 featuring a variety of traditional entertainment.

 There is a children’s fair, a road race, an arts and crafts fair, and live music at the event. 

Apple and Agriculture Days at Old Sturbridge Village, Sturbridge

For a more scaled-down fall festival in Massachusetts, make sure you stop by Old Sturbridge Village to celebrate the apple harvest.

At the end of October, you can visit the village for the Celebration of Cider and Music Festival (1 Old Sturbridge Village Rd).

The festival is put on to celebrate the harvest, teach the community about what goes into farm-to-table operations, and share in the bounty of unique New England agriculture.

Cape Cod Brew Fest

Looking for a festival to attend in Cape Cod this fall?

Look no further than the Cape Cod Brew Fest, an annual event held at the Cape Cod Fairgrounds (1220 Nathan Ellis Hwy) at the end of September.

You’ll love sampling 150 styles of beer from more than 60 breweries.

Samples are included in your ticket, and you’ll receive a custom glass as you exit.

Unfortunately, this is a pretty short celebration, lasting a few hours in mid-afternoon, but you’re sure to have an amazing time regardless!

Driftwood on an empty beach on the Cape Cod National Seashore in Massachusetts

Tennessee Williams Theater Festival, Cape Cod

Join the Provincetown Tennessee Williams Theater Festival in September to celebrate this classic playwright from the 1930s all the way to the 1980s.

There is no shortage of incredible drama during this amazing festival.

From his Broadway shows to his political pieces, there’s something for everyone to enjoy at the Provincetown Williams Theater Festival.

This is a worthwhile fall activity, especially if you’re hoping to attend a cultural festival.

Pilgrim Monument and Provincetown during sunset Provincetown, Massachusetts

Massachusetts Foliage Map

Wondering where to see foliage in Massachusetts?

Don’t miss the best days of the season to view the fall foliage at its peak!

Check out this New England Foliage Map for daily updates, predictions, and the most accurate tracking of the progress of the best fall foliage in Massachusetts.

You may also check out our guide to New England in fall.

Scenic view of farmland in Massachusetts in fall

Final Thoughts

We hope this guide can help you plan your visit to Massachusetts in the fall- and don’t forget to share your experience in the comments below.

Looking for more things to do in Massachusetts? You may find our other guides helpful:

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