2025's Towns In Massachusetts That Come Alive In The Fall
Although many areas in the country light up in the fall, the season is a true winner in New England, especially in Massachusetts. There are classic, charming towns lined with historic buildings, as well as magazine-worthy fall foliage, and all the classic flavors of the season, ranging from maple to pumpkin spice and apple. When the autumn months arrive, the state turns into a storybook. Check off a bucket list, including a bevy of pumpkin patches, apple orchards, and ghost whispers through historic towns. Though the state is an absolute masterpiece from corner to corner, there are some Massachusetts towns that stand out from the crowd in the fall.
Stockbridge
As part of the Berkshires, Stockbridge comes alive during the fall season. Surrounded by a countryside that feels like a living postcard, this timeless New England town is set against a backdrop of rolling hills and lush greenery. As peak foliage arrives in mid-October, the landscape transforms into a breathtaking canvas of deep reds, glowing oranges, and golden yellows. Take a scenic drive down Route 7 and admire the adorable farmhouses and wide-open fields touched by the warm hues of the changing season. Just off Route 7, take a moment to stretch your legs with a hike up Monument Mountain. From the summit, visitors are rewarded with breathtaking panoramic views of the vibrant fall foliage.
Get out and about in the fresh, cool air by strolling down the tree-lined Main Street. Take in the Colonial-style storefronts adorned with pumpkins, hay bales, and festive fall décor at every turn. Such a quintessential, charming downtown needs an accommodation to match. Cozy up at the iconic Red Lion Inn. The historic guesthouse is ideal for warming up after a well-spent day in Stockbridge.
Massachusetts overflows with autumn magic, and Stockbridge is no exception. Watch the night light up at The Incredible Naumkeag Pumpkin Show. Featuring over a thousand jack-o-lanterns, admire the mums, pumpkins, and gourds while sipping on cider. For a daytime excursion, head to the Berkshire Botanical Garden for the Annual Harvest Festival. Bring the whole family for the hay maze, haunted house, petting zoo, pony rides, and face painting. Before heading out, be sure to support the local vendors. Take home everything from handcrafted goods and plants to clothing and delicious treats.
Salem
Known as the Halloween Capital of the World and the Witch City, Salem is the spot for a fall adventure in Massachusetts. With peak foliage coloring the landscape in late October, the town provides the best scenery for Halloween and fall festivities. On the weekends, wander around the Haunted Happenings Marketplace at Derby Square. Browse handmade masterpieces in the same cobblestone town square that was featured in the cult classic film, Hocus Pocus.
Nothing beats the enchanting glow of a jack-o-lantern. Join Salem residents for the Hollowed Harvest and purchase a ticket to the Wicked Labyrinth and Madam Flim-Flam’s Psychic Emporium. The jack-o-lantern-laden maze, graveyard concert, pumpkin funeral, and paranormal theatrics perfectly capture Salem’s naturally spooky atmosphere.
Salem is brimming with eerie chills and spine-tingling thrills. Whether visitors are skeptics or true believers, the town offers a variety of ghost tours suited to every age and interest. Walk the dimly lit streets late at night to learn about Salem’s darker history, the haunting Salem Witch Trials, and the spirits that reportedly roam the town. For a more upbeat occasion, book the pub crawl, which includes ghostly legends and lore alongside Salem’s finest brews and cocktails. Brave visitors can wander through the Old Burying Point Cemetery, one of the oldest cemeteries in the country. With tombs dating back to the 17th century, the grounds are equally intriguing and unsettling.
Amherst
With deep literary roots and home to Amherst College, Amherst is an artsy Massachusetts college town that lights up in the fall. As much of the Pioneer Valley bursts into a living picture book with maples, oaks, and birches embracing the brighter shades of fall, the area comes alive with rich reds, burnt ambers, and sunlit yellows. With close proximity to the Connecticut River, Amherst is steeped in nature and boasts an idyllic countryside. Although the Amethyst Brook Conservation Area is striking all around, especially at the end of October, the Robert Frost Trail stands out as it passes through 10 communities. Trek this legendary trail and be spellbound by the Mount Holyoke Range, as well as wetlands, rural landscapes, and colorful woodlands.
Discover the heartwarming joy of country life in Amherst. Stock up on local produce at the Amherst Farmers Market, open from April to November. Gather apples, pumpkins, honey, maple syrup, and other seasonal delights to craft up fall goodies at home. For immediate satisfaction, the Amherst Farmers Market offers warm cookies, tender muffins, indulgent pastries, and comforting soups for purchase to enjoy alongside the crisp autumn breeze. Celebrate with Amherst locals at the Mill District General Store for the annual Fall Festival. Partake in small-town joy with a pie-eating contest, pumpkin painting, food samples, carnival games, and live music.
Stow
For those classic New England vibes, head to Stow for a phenomenal and memorable fall, especially since the area is renowned for its apple orchards. Sitting around 50 minutes away from Boston, Stow is bustling once the weather turns cooler. Although there are an abundance of orchards to choose from, Honey Pot Hill Orchards is a long-time favorite. Purchase a bag and stroll around the farm, picking apples and basking in the bright autumn sun. Make it a full-day excursion by waving hello to the farm animals, getting lost in the maze, and taking the ride of a lifetime on the hayride. Before heading out, stop at the on-site bakery for the famous apple cider donuts.
As the peak fall foliage in late October transforms Stow into a painting, grab a pumpkin spice latte or other warm, fall beverage and explore Leggett Woodland. Bring the kids for a magical walk down the Nature Discovery Trail. Watch the leaves produce a bright, diverse palette of radiant yellows, smoldering oranges, velvety reds, and toasty browns while discovering adorable statues along the Forest Tales Path.
Extend the journey by taking a quick 15-minute drive to the Assabet River National Wildlife Refuge, another fantastic spot for soaking in more of Massachusetts’ autumn charm. With 15 miles of trails, the area is popular for hiking, biking, and wildlife viewing. Bring a camera and spot the many waterfowl, birds, insects, reptiles, and amphibians that call the area home.
Williamstown
As another Berkshires autumn paradise, Williamstown radiates with warm tones, seasonal happenings, and lively community spirit in the cooler months. October brings the Sweetwood Fall Festival to the town. With a kids zone, craft vendors, live music, and food trucks galore, it is the best way to mingle with the locals and dive into fall fun. Typically held in September, the Williamstown Historical Museum’s Harvest Fair is another inviting hometown celebration. Dance along to the music by the Butterfly Swing Band in the old barn, partake in the cake auction, and check out the carnival booths and lawn games.
Start up the car and cruise along the Mount Greylock Scenic Byway. For the ultimate late October drive, be engulfed by the area's fiery landscape and travel through peaceful farmlands and rich forests. The road travels to the summit of Mount Greylock, the highest point in Massachusetts, offering a breathtaking panoramic view for miles on end.
Held annually by the Hopkins Memorial Forest, bring the whole family for the Fall Fest. Delighting hearts of every age, there is nothing quite like classic demonstrations to satisfy curiosity. From honeybee demonstrations, apple butter and cider making, and even cross-cut sawing, the live action is truly one-of-a-kind. After soaking up the hands-on learning, treat yourself to apple goodies and explore the kid-friendly activities.
Rockport
Get the best of both worlds in Rockport, Massachusetts. The picture-perfect seaport town on the Atlantic Ocean is where autumn’s rich colors blend perfectly with salty sea air and coastal scenery. Bask in this diverse mix at Halibut Point State Park. Trek the trails and be in awe of the rugged landscape, sweeping ocean views, and striking shades of crimson reds, golden yellows, and sunset oranges. Due to its geographical location, the peak colors don’t kick in until early November. While in the area, be sure to take a scenic drive down Route 127. Embrace the beauty of the changing season in New England with a cruise around Cape Ann’s vistas, including the legendary Rockport’s Motif No. 1.
A small-town gathering in Massachusetts during the fall is an unbeatable experience. October flourishes with the Rockport Harvest Fest. Savor local delicacies by sipping on brews from the Rockport Brewing Company or indulge in seasonal treats and fresh seafood straight from the source. Be entertained by the live music, seasonal crafts, animal exhibit, and face painting. The highlight of the Rockport Harvest Fest is definitely a classic apple pie contest.
For a more offbeat fall attraction, the Cape Ann Plein Air is an unforgettable October event held at various locations. As a haven for kindred souls of art and imagination, learn something new at the painting demos, make a new friend at the Gallery Walks and Talks, and share a moment of connection with the artists themselves at the reception.
Lenox
Just a short 15-minute drive from the New York border, Lenox is a tucked-away Massachusetts town with a thriving arts and culture scene. With fall colors peaking in mid-October, the natural wonderland is an adventurer's playground. Starting in Lenox, take the scenic route down Route 183, a road that leads all the way to Sandisfield. The drive comes alive with autumn shades in full bloom. Visitors may wish to stop at other cozy Massachusetts towns along the way, such as Great Barrington and Monterey. For an outdoor fall adventure, the Pleasant Valley Wildlife Sanctuary is a hotspot for hiking, wildlife watching, and soaking in the fiery countryside. Beavers are often spotted in the area, and the trails range in difficulty, making it appealing to all.
Embrace small-town charm with one of many thrilling festivities in Lenox. Every year, locals eagerly await the Lenox Apple Squeeze. Hosted in the downtown area, the lively day is filled with a kids carnival, live music, and just under 100 vendors. Browse handmade crafts, including candles, jewelry, quilts, and woodwork. Intriguing to food lovers, the Lenox Apple Squeeze proudly sells cider donuts, mile-high cakes, and kettle corn. Try some Mediterranean or Caribbean cuisine if you are feeling adventurous. Since many creatives are drawn to the town, it is only natural that Lenox hosts a Fall Art Walk. Held in September, just as the weather begins to cool, the event invites you to explore downtown, where pop-up stands showcase and sell local art.
Easthampton
Get ready to fill up the camera roll in Easthampton, especially in late October. The town boasts a prime location at the foothills of Mount Tom and in the Pioneer Valley. Get otherworldly views by exploring Mount Tom State Reservation, just outside of Easthampton. Grab a good pair of shoes and trek the Eyrie House Ruins Trail, the textbook definition of a fall adventure. The path weaves together the mysterious Eyrie House ruins with stunning panoramic views from the summit of Mount Nonotuck. Arcadia Wildlife Sanctuary is another fan favorite in Easthampton, especially in October. With a dedicated day for a Fall Foliage Photo Walk, register and learn about the tricks of the trade from nature photographer John Green. Admire the diverse terrain, surrounded by scarlet reds, rust oranges, and amber glows emanating from the dense woodlands.
Get to know Easthampton locals at one of their energetic events. Embark on a day of family fun at the October Harvest Festival. From pumpkin carving to horse wagon rides, face painting, bouncy inflatables, and spooky Halloween tunes, the Harvest Festival is an incredible way to celebrate the season. Wrap it all up with a blazing bonfire and discover why the fall in Easthampton is unforgettable. Late September brings the Easthampton Fall Makers Market to town. Support the locals and snag a one-of-a-kind souvenir from the vendors. Ranging from paintings to textiles, glassware, pottery, jewelry, and other creations, Massachusetts art is a sight to behold.
Concord
With a little bit of everything to love, Concord is a well-rounded getaway for a cozy, quintessential fall. The town exudes Hallmark movie appeal with tree-lined streets, historic colonial-style homes, and a timeless downtown with adorable shops. This makes Concord a fitting spot for fall escapades. While exploring the storybook downtown, book a stay at the Concord’s Colonial Inn. With the original structure built in 1716, the accommodation is home to its fair share of ghostly tales. Guests claim Room 24 experiences the most paranormal activity due to its ties to the Revolutionary War. Just steps from the hotel, Sleepy Hollow Cemetery offers a hauntingly beautiful glimpse into the past. Stroll past headstones that trace back to the 19th century, including famous literary figures such as Abigail May Alcott and Nathaniel Hawthorne.
Verrill Farm shines as one of the finest destinations for autumn magic in Concord. Throughout October weekends, visitors can pick their perfect pumpkin to take home for seasonal decor, baking, or carving. New to Verrill Farm, get in on the fun at the Pumpkins and Potions Halloween Party. The 21+ event is an evening jam-packed with Halloween-themed games, desserts, and spooky beverages to go along. For family-friendly festivities, the annual Harvest Fest is thrilling for all, featuring live music, a petting zoo, raffles, games, and prizes. Stop by the farm for a fresh, homemade pie bursting with fall flavors. Nothing beats a good old Kentucky Bourbon Pecan or Apple Cranberry Pie while the weather is cool.
Nobody Does Fall like Massachusetts
When it comes to fall destinations in the United States, New England is typically at the top of the list. With world-famous bright fall foliage, ghost tours galore, fall festivals, pumpkin picking, and all the apple goodies, Massachusetts is one of the top picks for autumn adventures. Catch a ghost or two at the historic inn in Concord’s haunted Colonial Inn or party all night long in Salem’s witch city. Few things capture the soul of Massachusetts like a winding autumn drive, where the landscape blazes with vibrant colors. Get a cider or pumpkin latte and hit the road. Cruise along the Mount Greylock Scenic Byway or Rockport’s Route 127 for some of the most incredible views. Finish off the fall extravaganza with a cider donut and see why Massachusetts is one of a kind when the air turns crisp.
