Summary

• Key takeaways:
• Greenfield, Lenox, and Northampton are beautiful towns in Massachusetts that offer incredible fall experiences, including scenic trails, apple and pumpkin picking, traditional festivals, and cultural events.
• Hadley is a less crowded town with vibrant fall foliage, offering hiking and biking options at Mount Holyoke Range State Park and peaceful strolls at Lake Warner.
• Douglas, Cape Cod, and Orange also have unique fall celebrations, such as the Oktoberfest in Douglas, Cape Cod Brew Fest, and the North Quabbin Garlic and Arts Festival in Orange.

Autumn in Massachusetts is full of glory, where the crisp air, vivid hues of flaming gold and orange, pumpkin carvings, Halloween, and carnivals are in full throttle. Whereas the spectacular display in Massachusetts is unmatched overall, few towns celebrate fall like no other. Visit these beautiful towns of Massachusetts to experience the fall in its full glory.

UPDATE: 2023/10/09 18:58 EST BY REENA JAIN

More Massachusetts Towns That Are Celebrating The Fall Season Perfectly

Soaking in the breathtaking fall foliage is one of the most amazing things to do in Massachusetts, and the state is full of lovely towns where one may have the best experience of this natural grandeur. This list has been updated with four more of the best fall towns in Massachusetts, offering incredible natural surroundings and exciting experiences.

14 Greenfield

For those seeking a fall escape from the noisy crowds, Greenfield is the ideal town in Massachusetts. The town, with amazing fall scenery, offers a range of scenic trails for hikers to appreciate the beauty of the season to the fullest. There are also various farms for apple and pumpkin picking, as well as numerous nice cafes, shops, and galleries in the downtown area for a variety of fascinating and delightful experiences. Traditional fall festivals bring the town to life and let visitors enjoy the true spirit of the season with customary fare and celebrations. The neighboring Connecticut River provides kayaking and hiking options for those who enjoy the great outdoors.

• Accommodation: Hampton Inn & Suites Greenfield
• Address: 184 Shelburne Rd, Greenfield, MA 01301, United States
• Amenities: Fitness center, Free Wi-Fi, Tea/coffee maker, Free parking

13 Lenox

Lenox is another popular fall destination in Massachusetts, and for good reason. The town transforms into a vibrant tapestry of autumn colors, enticing visitors to enjoy some beautiful moments. From leisurely strolls along historic streets to exploring renowned attractions like The Mount and Kennedy Park, there is so much to do and see in the town to enjoy fall splendor. Plus, cultural events such as the Tanglewood Music Festival, as well as seasonal cuisines at local restaurants and apple picking at a neighboring orchard, add to the festive atmosphere.

• Accommodation: Courtyard by Marriott Lenox Berkshires
• Address: 70 Pittsfield Rd, Lenox, MA 01240, United States
• Amenities: Indoor pool, Fitness center, Restaurant, Bar/Lounge, Free Wi-Fi

12 Northampton

Northampton, Massachusetts, is a captivating destination with the vibrant colors of autumn foliage as well as various fall festivals and live performances. Offering rich cultural experiences amid breathtaking fall splendor, this small town is among the best in Massachusetts. Add to that a range of scenic hiking trails, lush farms, cozy cafes, and local farm-to-table dining options that make a fall trip full of incredible experiences. Hiking routes and magnificent panoramas in the adjacent Holyoke Range are other popular attractions for outdoor lovers.

• Accommodation: Fairfield Inn & Suites by Marriott Springfield Northampton/Amherst
• Address: 115A Conz St, Northampton, MA 01060, United States
• Amenities: Indoor pool, Fitness center, Bar/Lounge, Free Wi-Fi, Coffee machine

11 Hadley

Hadley is one of the least crowded towns in Massachusetts to visit in the fall, and its vibrant beauty is second to none. With majestic autumn colors, hiking through its nature trails and driving on Route 47 is like roaming in heaven. Excellent hiking and biking options are available at Mount Holyoke Range State Park, which also offers expansive vistas of the changing leaves. Additionally, there are wonderful fishing and peaceful strolls through the fall foliage at Lake Warner.

• Accommodation: Hampton Inn Hadley-Amherst Area
• Address: 24 Bay Rd, Hadley, MA 01035, United States
• Amenities: Indoor pool, Fitness center, Free Wi-Fi, Tea/coffee maker, Free parking

10 Douglas

Douglas is a town in Southern Worcester County, Massachusetts. The Oktoberfest In Douglas, a downtown street festival, has garnered a lot of attention due to the diversity it beholds. The festival has various food stalls, games, rides, entertainment programs from singers and dancers, activities such as The Huge Slide, Moonwalk, and Train, and booths celebrating homemade sandwiches, soups, cookies, and cakes. This year will feature a Berkshire brewing tent with live music. This event is held on October 1st from 9 am - 4 pm.

• Accommodation: Hampton Inn & Suites Providence/Smithfield
• Address: 945 Douglas Pike, Smithfield, RI 02917, United States
• Amenities: Indoor pool, Fitness center, Free Wi-Fi, Tea/coffee maker

9 Cape Cod

A hook-shaped peninsula called Cape Cod in Massachusetts has plenty of magnificent beaches, historic landmarks, restaurants, and worthy tourist attractions. Although it is an all-year destination, with fall, the Cape Cod Rail Trail turns more magnificent for cyclists. Fall makes it perfect for biking, hiking, kayaking, and the crowd, which is less common. The Cape Cod Brew Fest is an opportunity to taste almost 300 types of beer along with living music and delectable food. Also, there are many art and music festivals in October and November. An event called Well Fleet Oyster fest is an annual event in Cape Cod that has garnered a lot of attention. Particularly for shellfish and oyster lovers, it also has music performances, art, local beer, and many other contests. This event is held in mid-October.

• Accommodation: The Provincetown Hotel at Gabriel's
• Address: 102 Bradford St, Provincetown, MA 02657, United States
• Amenities: Room service, Free Wi-Fi, Tea/coffee maker

8 Orange

Orange is a town in Franklin County, Massachusetts, which has serene as well as adrenaline-fulfilling activities. Having commercial skydiving, Jump Towns offers both Tandem and Accelerated Free fall training. The North Quabbin Garlic and Arts Festival at Fosters Farm In Orange is quite quirky. It is something for garlic lovers, and the tagline states, “The Festival That Stinks.” The cuisine is infused with garlic in huge amounts, as the art, music performances, and other fun activities accompany the event. The event is held on Oct 1st and 2nd.

• Accommodation: The Inn at Crumpin-Fox
• Address: 71 Northfield Rd, Bernardston, MA 01337, United States
• Amenities: Free Wi-Fi, Private bathroom, Coffee machine, Air-conditioned

7 Wareham

A town in Plymouth County, Massachusetts, has the Cranberry Harvest Fest celebrating the tiny red fruit. There are bog tours, a firelight parade, helicopter rides around the area, crafts related to cranberry, as well as people exploring the cranberry farmers market. There are cranberry treats in the form of cranberry cream puffs, juices, scented candles, and more. The event began in 1973 and hosts around 150,000 visitors approx a year. The event is held on October 8th and 9th.

• Accommodation: TownePlace Suites by Marriott Wareham Buzzards Bay
• Address: 50 Rosebrook Pl, Wareham, MA 02571, United States
• Amenities: Indoor pool, Fitness center, Free Wi-Fi, Coffee machine, Free parking

6 Stockbridge

A town in Berkshire County, Western Massachusetts, celebrates the annual Berkshire Botanical Gardens Harvest Festival, marking the onset of autumn. The event has an upbeat vibe with entertaining activities, including hayrides, pumpkin tossing, a hay maze, and visiting haunted houses, as well as stalls selling clothing and jewelry. Held for two days, this festival is located at 5 West Stock Bridge Road. The event is held from 8th Oct - 9th Oct.

• Accommodation: The Red Lion Inn
• Address: 30 Main St, Stockbridge, MA 01262, United States
• Amenities: Outdoor pool, Fitness center, Restaurant, Bar/Lounge, Room service

5 Topsfield

Topsfield is a town in Essex County, Massachusetts, and celebrates fall with its Topsfield fair. Known as America’s Oldest County Fair, this traditional fair has a lot of contests such as an Extreme Vertical Competition of Swimming for dogs, a hot dog eating contest, stock farm tractor pull, gymnasts performing high wire act stunts, visual and culinary arts, parades, flower production and more. For 200 years, the fair has been drawing crowds in huge numbers, gravitated by classic cuisine, entertainment, and cultural vibes. The event is held from Sept 30th - Oct 10th.

• Accommodation: Sonesta Select Boston Danvers
• Address: 275 Independence Way, Danvers, MA 01923, United States
• Amenities: Outdoor pool, Fitness center, Restaurant, Bar/Lounge, Free Wi-Fi

4 Salem

Salem in Massachusetts has the reputation of having spine-chilling Halloween festivals. The prime Festival Of The Dead has various events such as Dinner With The Dead, The Salem Psychic Fair & Witches Market, Witches Magic Circle, Mourning Tea, and so much more. In short, the festival celebrates macabre costumes and bizarre rituals. The festival is held for an entire month with various activities lined up. The event is for the entire month of October and costs around $50 to $75, definitely for anyone seeking spooky experiences.

• Accommodation: Salem Waterfront Hotel & Suites
• Address: 225 Derby St, Salem, MA 01970, United States
• Amenities: Indoor pool, Fitness center, Restaurant, Bar/Lounge, Room service

3 Greater Boston

With its historic architecture and the fall foliage in Boston parks, Boston turns quite dreamy. A walk along the city’s Freedom Trail, along with a visit to Boston’s Faneuil Marketplace, are primary activities to be done in the Fall. Apart from this, there is the Ghost & Gravestones Tour, which explores Boston’s spine-chilling haunted places & burying grounds nearly 400 years old. For nature lovers, there is the Emerald Necklace & Fall Foliage tour, and for shopping, one can resort to “The Newbury Street,” which has imported Italian dresses, restaurants and a few outlets for sports lovers. On your visit to Boston, don't miss one of the world’s greatest orchestras, “The Boston Symphony Orchestra,” with incredible acoustics and beauty in the historic location.

• Accommodation: The Liberty, a Luxury Collection Hotel in Boston
• Address: 215 Charles St, Boston, MA 02114, United States
• Amenities: Fitness center, Restaurant, Bar/Lounge, Room service

2 Princeton

The Applefest at Wachusett Mountain in Princeton is one of the popular ways to celebrate fall in this region. With giant pumpkins, an apple and blueberry pie eating contest, live music, and the unique opportunity to meet eagles, hawks, falcons, and owls, this fest is lively in every manner. Admission is $11 for advance tickets and $14 on the spot, whereas, for kids, it's $6 and $9. The event is held on Oct 14th and Oct 15th.

• Accommodation: Beechwood Hotel
• Address: 363 Plantation Street, Worcester, MA 01605
• Amenities: Fitness center, Restaurant, Bar/Lounge, Room service

1 Carver

Carver, a town in Plymouth County in Massachusetts, celebrates King Richard’s Faire, a fall festival where one will be enthralled by activities galore. One may witness acrobats, aerialists, fire-eaters, knights on horseback, sports like archery, and esoteric stuff like fortune-telling. Celebrated on this 80-acre wooded site, the festival celebrates the spirit of the Renaissance. The festival is held almost every month with plenty of fun things lined up. The event is held from Sept 2nd - Oct 22nd.

• Accommodation: Hotel 1620 Plymouth Harbor
• Address: 180 Water St, Plymouth, MA 02360, United States
• Amenities: Indoor pool, Fitness center, Restaurant, Bar/Lounge