Fall in New England is nothing short of magical. Crisp air, fiery foliage and the scent of fresh apple cider donuts will convince you that this is the best time of year to explore Massachusetts. Luckily, you don’t need a car to experience it! From dazzling leaf-peeping trails to historic towns bursting with charm, the best fall day trips from Boston are just a train ride away. Thanks to the MBTA Commuter Rail and Keolis massAdventures, you can savor all the sights, colors, and flavors of the season without the hassle of driving or parking.
Here’s your ultimate guide to the best spots to see fall foliage, fall tours outside of Boston, seasonal festivals, and cozy autumnal adventures – all perfect day trips from Boston Massachusetts to add to your fall bucket list.
Concord: Historic Walking Tour & Fall Foliage
Take a ride on the Fitchburg line to Concord Station, where you’re welcomed by a mix of history and autumnal ambience. Concord is the birthplace of the American Revolution. Subsequently, you can learn all about this significant history on a Guided Historical Walking Tour with Keolis massAdventures. Walk the same paths once taken by revolutionaries while surrounded by blazing orange, bright yellow, and deep, fiery red foliage. Stroll past Revolutionary War landmarks, cross the North Bridge, and visit the Wright Tavern.
Book lovers will enjoy stepping into the pages of “Little Women” on A Day Trip to Louisa May Alcott’s Orchard House. The Orchard House is where author Louisa May Alcott lived when she wrote, “Little Women”. Walk the very same halls that inspired the March sisters’ family home, see their rooms and the desk that Louisa May Alcott sat and wrote at.
Wrap up your spooky season visit with a walk through Sleepy Hollow Cemetery. Filled with trees whose leaves paint the landscape with their colorful foliage, this beautifully historic cemetery dates back to 1855. The 17-acre heart of the cemetery was designed by Frederick Law Olmsted. Olmsted was a famed landscape designer whose work includes The Emerald Necklace, Fairsted, Moraine Farm, World’s End, Central Park, and the Biltmore Estate. A visit to Sleepy Hollow Cemetery isn’t complete without stopping at Author’s Ridge. Here you can pay respects to famous authors who lived in Concord, including Louisa May Alcott, Henry David Thoreau, and Nathaniel Hawthorne.
Rockport: Picturesque Seaside Escape
Hop on the Newburyport/Rockport line to Rockport Station for one of the most picturesque seaside towns in Massachusetts. Rockport is an iconic fishing town where the yellow, oranges and red of fall meet the deep blue Atlantic Ocean. Visit Motif #1, stroll along Bearskin Neck, and soak in the rare sight of ocean waves framed by colorful autumn trees. October is an exciting time to visit as the annual Cape Ann Plein Air Festival is happening! Cape Ann is known as the birthplace of American Plein Air painting. Late 19th century American artists who studied the technique in Paris chose to settle on Cape Ann in part because of its bustling art community, but also due to its unique landscapes, lighting and coastline. Celebrate its artistic heritage and admire the foliage on a fall day trip to this picturesque coastal town.
Ipswich: Seaside Foliage Adventure
Climb aboard the Newburyport/Rockport line and head to Ipswich for some of the most breathtaking fall landscapes in Massachusetts. A short walk from the station is the High Street Historic District. Not only is the district home to incredible, well-preserved historic homes, but it’s also full of breathtaking trees who truly shine in the fall. Sunshine-yellows and amazing oranges falling from the trees in this district will make you reach for your camera.
Rolling hills lined by colorful trees, trails where you’ll feel as though you’re walking into an autumnal painting, and gardens showcasing fall blooms, the Crane Estate is a must-visit. With Keolis massAdventures, you can easily visit the Crane Estate for an outdoor Guided Nature Walk around Castle Hill on the Crane Estate. Or, sign up for an indoor Guided Tour as a Guest of the Cranes of Castle Hill, where you’ll admire the changing fall landscapes from within the house as you explore the different rooms.
Salem: Spooky Charm Without the Halloween Crowds
Salem may be most popular for Halloween in October, but September and November offer the same charm without the massive crowds. Take the Newburyport/Rockport line to Salem Station and enjoy a short walk to downtown. Explore the historic waterfront area, wander cobblestone streets lined with fall decor and visit The House of the Seven Gables. History buffs will want to visit the Salem Witch Museum, where you’ll walk through life-size stage sets and hear the tales and hysteria surrounding the Salem Witch Trials of 1692. Just a short walk away, the Peabody Essex Museum has an exhibition on the Salem Witch Trials of 1692. Court documents and historic artifacts, part of the largest collection of witch trail materials in the world, brings viewers back to the time of the trials.
An autumn visit to Salem wouldn’t be complete without a walk around downtown. Grab a cozy cup of tea from Brew Box on Essex to enjoy as you meander around admiring the foliage. Salem Commons is a must-visit, with different kinds of trees showing off their reds, oranges, yellows and greens at different times, creating a stunning colorful backdrop that can change in just a few days!
For those who want to visit during October for Halloween celebrations, check out Salem Haunted Happenings. These events are held throughout the month with grand parades, psychic & spiritual experiences, tarot readings, ghost tours, walking & trolley tours, haunted houses, live entertainment and more!
Topsfield: The United States’ Oldest Agricultural Fair
Celebrate autumn at one of Massachusetts’ iconic fairs and festivals. The Topsfield Fair is America’s oldest agricultural fair. Featuring live entertainment, giant pumpkins, a demolition derby, barnyard animals, and a midway with a Ferris wheel and other carnival rides, there’s fall fun for everyone! Enjoy apple cider doughnuts, giant baked potatoes and warm, fresh apple crisp. Easily get to The Topsfield Fair with Keolis massAdventures, our Topsfield Fair Special Event Package includes round-trip transportation from Boston via Commuter Rail and shuttle van, your Commuter Rail Weekend Pass, entry ticket to the fair, and a $10 Food & Beverage Voucher. Experience a classic New England fair without the stress of driving, traffic & parking!
New Bedford: Autumn in a Bustling Coastal City
Once the whaling capital of the world, New Bedford now offers an incredible mix of culture, history and food. Ride the Fall River/New Bedford line to New Bedford Station to visit the heart of downtown. From there, you can walk along the historic waterfront, admiring views of the harbor and colorful parks and gardens along the way. Walk up the historic cobblestone streets, into town for more large, old trees showcasing their fall best.
A trip to New Bedford isn’t complete without a Portuguese pastry and a visit to the New Bedford Whaling Museum. Thankfully, you can do both when you schedule your day trip with Keolis massAdventures! We’ll drive you to the New Bedford Whaling Museum for a self-guided exploration into the history of the city’s whaling culture, then you’ll embark on a culinary journey into the city’s food culture! From giant (replica) whale hearts to a half-size replica whaling ship, sweet treats, cool bites and refreshing sips, this New Bedford Whaling Museum & Food Trip Adventure is one you’ll be talking about for years to come!
Ayer & Harvard: Trails & Museums Bursting With Color
Nestled in Nashoba Valley, the towns of Ayer and Harvard are truly autumnal hidden gems. Grab the Fitchburg/Wachusett line train to Ayer Station. From here, the Nashua River Rail Trail Ayer access point is only a 2 minute walk. The Nashua River Rail Trail offers 11 miles of trail, perfect for biking or fall foliage sightseeing. The tree-lined path explodes with color in the fall, making it a beautifully scenic walk.
Rolling hills and breathtaking foliage provide show-stopping views at The Fruitlands Museum in Harvard. The Fruitlands Museum offers indoor and outdoor exploration opportunities with art and history showcased within the museums and nature abound. Enjoy galleries highlighting Shaker life, Native American history, and Transcendentalist culture. Then, walk natural trails winding around the property and frolic through open meadows dotted with red and gold leaves. Plan your visit to The Fruitlands Museum with Keolis massAdventures, to easily and conveniently get to the museum.
Boylston: Flowers & Foliage
*Disclaimer: you’ll need to book with Keolis massAdventures for this trip!
Fall brings a whole new set of blooms at the New England Botanic Garden at Tower Hill! Take the Framingham/ Worcester line to Grafton Station, where our van will be waiting to bring you on a day trip to the New England Botanic Garden. You’ll be transported to a fall wonderland, full of dazzling displays, including blooming chrysanthemums, ornamental grasses, and late-blooming perennials. Stroll through gardens full of fall blooms and woodland trails bursting with colorful foliage! Not to mention, you’ll want to make a point of stopping to admire the Wachusett Reservoir views. Also, until October 12, 2025, you can see artist George Sherwood’s Art in Motion exhibit throughout the gardens. Art in Motion showcases the movements of nature within its 17 different kinetic sculptures.
Middleborough: Cranberry Bog Adventures
Nothing says fall in New England like a cranberry bog! Hop on the Fall River/ New Bedford line and ride until the Middleborough Station. Book with Keolis massAdventures so your ride to the bog is waiting for you! Otherwise, a rideshare service will be needed to get around Middleborough. Dive into the history of New England’s native superfruit, learning how cranberries are grown, cultivated and harvested. You’ll even get to try dry picking on the Guided Tour of a Local Cranberry Farm!
For a “berry” cool, once-in-a-lifetime adventure, check out Become a Cranberry Bogger for a Day Tour. You’ll suit up to go into the flooded cranberry bogs! Surrounded by a sea of red cranberries, this is truly a bucket list experience. For those worried about “giant bog spiders” you might have heard about, don’t be! The only spiders we’ve seen were small, harmless, and not interested in humans – only other insects in the bogs!
Fall River: Boardwalk Foliage & Spooky Legends
Fall River shines in autumn, with the Taunton River reflecting colorful views of foliage along the boardwalk and Battleship Cove. Hop aboard the Fall River/ New Bedford line and ride until Fall River Depot. You’ll disembark right in front of the waterfront, perfect for convenient, car-free adventures. Stroll down the boardwalk to admire foliage, grab a sweet treat, visit Battleship Cove, or spin around a historic carousel.
For those who love a good scare, visit the Lizzie Borden House, where the infamous murders took place in 1892. Just a five-minute walk from the Fall River Depot, this historic house can easily be visited without a car. Take a guided tour, learn the chilling history, and even book a night if you dare.
Why Travel With Keolis massAdventures This Fall?
Parking at these popular spots can be a headache, not to mention you’re travelling sustainably by choosing to take the train. Plus, when you book with us you get round-trip transportation from Boston plus tickets to your chosen activity all bundled into one tour package! Whether it’s cranberry bog tours, historic walking tours or a seasonal festival, our curated car-free fall adventures let you relax and enjoy the ride while making unforgettable autumn memories.
Your Best Car-Free Fall Yet
Whether you’re craving colorful fall foliage or crisp seaside air, these fall day trips from Boston are sure to bring the season to life. From historic Concord to spooky Salem, fall festivals and cranberry harvests, you’ll find countless ways to celebrate autumn, no car required. So, grab a flannel, hop on the train, and make this fall your favorite season yet!
