There’s something about fall in Massachusetts that makes you want to get out and explore. The air gets cooler, the leaves turn brilliant shades of red and gold, and weekends fill up with fairs, festivals, cider donuts, live music, local food, and traditions that only come around once a year.
The only downside? Everyone else has the same idea.
Fall weekends can mean crowded highways, limited parking, and spending more time sitting in traffic than enjoying the season. But you don’t necessarily need a car to experience some of Massachusetts’ best fall events.
From America’s oldest agricultural fair and a mountaintop celebration surrounded by fall foliage to a Renaissance village filled with knights and jousting tournaments, some of the state’s most memorable fall festivals can be reached using the MBTA Commuter Rail, with a shuttle or rideshare completing the final leg of the journey.
Here are three Massachusetts fall festivals worth adding to your 2026 calendar and how to get to each one without driving from Boston.
Topsfield Fair: October 2–12, 2026
If there’s one event that captures the feeling of a classic New England fall fair, it’s the Topsfield Fair.
Founded in 1818, the Topsfield Fair, located in Topsfield Massachusetts, is known as America’s oldest agricultural fair and has grown into one of Massachusetts’ most beloved autumn traditions. For 11 days each October, the fairgrounds come alive with agricultural competitions, animals, entertainment, midway rides, enormous pumpkins, local vendors, and more fair food than you could possibly try in one visit.
Despite its size, agriculture remains at the heart of the experience. Visitors can wander through livestock barns, explore flower and produce displays, watch traditional horse and oxen pulling competitions, and learn more about New England’s agricultural heritage.
Then there are the pumpkins. The annual All New England Giant Pumpkin Weigh-Off has become one of the fair’s signature events, bringing growers together to see whose enormous pumpkin will tip the scales at the highest weight.
Beyond the agricultural traditions, there’s plenty to keep you busy for an entire day. Ride the Ferris wheel, catch live entertainment, browse hundreds of vendors, watch a parade, or simply make your way through the fairgrounds sampling everything from apple pie and cinnamon rolls to fried Oreos, barbecue, seafood, and other fair favorites.
The result is an experience that blends generations of New England tradition with the energy of a modern county fair.
Best For: Full-day adventures, families, food lovers, first-time Massachusetts visitors, and anyone looking for a quintessential New England fall experience.
Festival Highlights
- Famous Giant Pumpkin Weigh-Off
- Livestock barns and agricultural competitions
- Horse and oxen pulling
- Flower, fruit, and vegetable exhibits
- Carnival rides and midway games
- Live entertainment
- Local vendors and demonstrations
- Classic New England fair food
Getting to the Topsfield Fair Without a Car
The Topsfield Fair is one of those destinations where getting there can be one of the most frustrating parts of the day. Fall traffic on the North Shore can be heavy, and parking areas fill quickly on popular weekends.
That’s why Keolis massAdventures offers a Topsfield Fair Ticket Package from Boston that takes care of the transportation and admission for you.
Your package includes:
- MBTA Commuter Rail Weekend Pass
- Round-trip shuttle transportation between the Commuter Rail and the fairgrounds
- Admission to the Topsfield Fair
- $12 food voucher to use at the fair
Instead of spending your morning navigating traffic and searching for parking, you can board the Commuter Rail in Boston and let us handle the rest. It’s one of the easiest ways to experience one of New England’s most iconic fall traditions without a car.
Wachusett Mountain AppleFest: October 17–18, 2026
For fall foliage with a view, head west to Wachusett Mountain located in Wachusett, Massachusetts.
Wachusett Mountain may be best known as a winter destination, but October transforms the mountain into one of Central Massachusetts’ most scenic places to celebrate fall.
AppleFest combines mountain views, seasonal food, live entertainment, local vendors, and plenty of apple-inspired treats into one full weekend of fall festivities.
One of the biggest reasons to visit is the scenery.
Take the scenic SkyRide toward the summit for sweeping views of the surrounding landscape as the forests below turn shades of orange, yellow, and red. It’s a completely different way to experience Massachusetts foliage—and you don’t need to hike to enjoy the view.
Back at the base of the mountain, the festival continues with live music, local crafters, food trucks, entertainment, and plenty of opportunities to indulge in the flavors of the season.
Hot apple cider? Absolutely.
Fresh cider donuts? Of course.
Apple treats, seasonal drinks, and local brews? You’ll find those too.
Wachusett’s 42nd annual AppleFest takes place over two weekends in 2026, making it one of the mountain’s biggest fall celebrations of the year.
Best For: Foliage seekers, couples, families, photographers, foodies, and anyone who wants a mountain escape without spending the day hiking.
Festival Highlights
- Scenic SkyRide with panoramic foliage views
- Hot apple cider and fresh cider donuts
- Apple-inspired food and drinks
- Live music
- Magic and circus performances
- Local craft vendors
- Food trucks
- Local breweries and seasonal beverages
- Family-friendly activities
Getting to Wachusett Mountain by Commuter Rail
Leave Route 2 traffic behind and take the Fitchburg Line from Boston Wachusett Station,.
Wachusett Mountain promotes seasonal transportation between Wachusett Station and the mountain during AppleFest, making the festival an especially appealing option for Boston-area travelers who don’t have access to a car.
Because shuttle and rail arrangements can vary by festival date, check Wachusett Mountain’s current AppleFest transportation information before heading out.Once you arrive, you can spend the day enjoying the mountain and fall scenery without worrying about the drive home.
Photo Courtesy of MassLive
King Richard’s Faire: Weekends September 5–October 25, 2026
Looking for a fall festival that goes far beyond pumpkins and cider donuts?
Travel back in time at King Richard’s Faire in Carver, Massachusetts New England’s largest Renaissance festival and one of Massachusetts’ most unique autumn traditions.
On weekends from September 5 through October 25, the fairgrounds transform into the fictional village of Carvershire, where knights, royalty, musicians, acrobats, artisans, and costumed villagers create an immersive Renaissance world.
This isn’t an event where you simply walk around and look at displays. Entertainment is happening all around you.
You might stumble across musicians and performers while walking between stages, watch artisans demonstrate their crafts, catch aerialists or fire eaters performing, or find yourself cheering as armored knights charge toward one another on horseback during one of the day’s jousting tournaments.
King Richard’s Faire features hundreds of performers across eight stages and throughout the village, meaning no two visits or even two hours at the Faire feel exactly the same.
Food is part of the experience, too. Giant turkey legs may be the iconic choice, but you’ll also find an assortment of themed dishes and drinks throughout the grounds.
And yes, dressing up is encouraged.
You’ll see everything from elaborate historically inspired costumes to pirates, fairies, fantasy characters, and visitors who simply showed up in jeans to see what all the excitement is about. You don’t need a costume to participate, but if you’ve been waiting for an excuse to wear one, this is it.
Best For: Couples, families with older children, fantasy fans, history lovers, groups of friends, and anyone looking for something completely different from a traditional fall festival.
Festival Highlights
- Jousting tournaments featuring knights on horseback
- Hundreds of performers
- Eight entertainment stages
- Musicians, acrobats, fire eaters, and other roaming entertainers
- Renaissance marketplace
- Handcrafted goods and artisan demonstrations
- Games and rides
- Giant turkey legs and themed food
- Elaborate costumes and immersive characters
Getting to King Richard’s Faire by Commuter Rail
You don’t have to drive all the way from Boston to Carver to experience the Faire. Take the Fall River New Bedford Line from Boston to Middleboro Station, and complete the final portion of your trip to the fairgrounds by rideshare. Once you step through the gates, though, Boston will feel considerably farther away than a train ride.
Make the Most of Fall in Massachusetts Without the Car
From giant pumpkins and cider donuts to mountaintop foliage and jousting knights, fall festivals are one of the best ways to experience autumn in Massachusetts. And with the Commuter Rail, you don’t necessarily need a car to get there.
Instead of spending your fall weekend sitting in traffic or searching for parking, make the journey part of the adventure. Hop aboard the train from Boston, enjoy the scenery along the way, and connect to some of the state’s most exciting seasonal destinations.
Want to make it even easier? Keolis massAdventures offers fall day trips from Boston that combine Commuter Rail travel with last-mile transportation and admission to popular destinations like the Topsfield Fair, working cranberry farms, and deCordova Sculpture Park
Fall in New England never lasts long, so don’t wait until the leaves are already falling to make your plans.Grab your favorite flannel, bring your camera, and start exploring some of the best fall experiences in Massachusetts are only a train ride away.
