Massachusetts is a popular destination in the summer, but fall can be the best time to visit. As temperatures start to cool down, the air turns crisp, and travelers head away for the season, the fall in Massachusetts offers quintessential New England activities like apple picking and leaf-peeping. It’s one of the best places to visit in the fall season.
If you are visiting the area, most of these things can be done as day trips, if you have a car on your trip. It’s a pretty small state! Massachusetts residents can also enjoy these activities on weekends and holidays in the fall. Here are some of our favorite ways to enjoy the fall in Massachusetts.
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Ways to Enjoy the Fall in Massachusetts
Learn About History By Walking the Freedom Trail
Massachusetts, especially Boston, offers so many different ways to learn about history. Take advantage of the cooler temps and walk the Freedom Trail in downtown Boston. The trail can be explored on your own, or you can book a walking tour.
There are sixteen official sites of the Freedom Trail, including the Boston Common, Old North Church, and the USS Constitution. While you are in Boston, you can also visit the Public Garden, Newbury Street, and Faneuil Hall.
Apple Picking/ Pumpkin Picking
Apple picking and pumpkin picking are must-do fall activities in Massachusetts, and luckily there are lots of farms to visit. Be sure to check their schedules before leaving because sometimes picking is done for the day/season. In addition, some of the farms require reservations for picking. Many of these farms are in small towns and you’ll get to see some of the fall colors and beautiful scenery while taking the scenic drive.
Tangerini Farm in Millis, Massachusetts, is a great choice for families. It offers U Pick of apples, flowers, tomatoes, and more (depending on the season). They also have a restaurant and an ice cream stand. In late September and October, you can pick pumpkins.
Belkin Lookout Farm in Natick, Massachusetts is another one of our favorites. This farm offers U Pick apples and pears in the fall. In addition, they offer a fabulous, outdoor restaurant with their own beer and hard cider. You can also pick up fruit, cider, beer, apple cider donuts, and more in their farm shop.
Another family favorite is Honey Pot Orchards in Stow, MA. This beautiful farm offers U Pick apples and pears, the largest hedge maze in North America, hayrides, and farm animals. It does get busy on the fall weekends, so visit early in the day or during the week.
Tougas Family Farm in Northborough, MA also offers apple picking in the fall. The farm also has a playground, farm store, and barnyard animals.
Leaf Peeping
Peak foliage season usually happens in late October, but we are already seeing some leaves start to change as the weather is getting cooler. There are lots of places to drive around town to see leaves, although my favorite option is taking a day trip to New Hampshire where the leaves on the mountains are absolutely gorgeous. In my opinion, it’s the best fall foliage.
Even if you are doing these other activities, driving through the New England towns in the autumn season can be absolutely gorgeous. Take time to look around.
Timing your New England trip to try to see the peak colors can be a little challenging. While you want to make sure you don’t go too early to see the best fall color, one bad rain/wind storm can knock the beautiful leaves off the trees. So be sure to check the weather forecasts.
Corn Mazes
Getting lost in a corn maze can be a fun fall activity, especially in the gorgeous fall weather. For those up to the challenge, the Davis Mega Maze in Sterling, MA has eight acres of corn and almost three miles of paths. There are Maze Masters in the maze to help with directions if needed. In addition, there are fun activities throughout the maze.
Sauchuk’s Corn Maze and Pumpkin Patch is also located in Plympton, MA. Purchase tickets in advance to ensure entry.
Cranberry Harvesting in A Cranberry Bog
Did you know that cranberries are grown and harvested right in Massachusetts? For a unique experience, visit a local cranberry bog, where you may even be able to harvest your own cranberries.
Benson’s Pond, located in South Middleboro, MA, has over 40 acres of cranberry bogs. They offer small groups the opportunity to be cranberry boggers for a day. This experience needs to be booked and is for those 16 and over. Cranberry bogging season runs from late September to November.
Visit Salem, MA
Salem, Massachusetts, the historic town and home of the Salem Witch Trials, is a great place to visit in the fall—especially in October. Salem offers its Salem Haunted Happenings event, with activities every day of October. It’s one of the best things to do to celebrate Halloween.
In past years, we’ve visited Salem in October, and it’s so much fun. There are outdoor markets, magic shows, lectures, a 5k, and more. Visit their website for full details on what events will be offered.
While in Salem, you can also visit the Peabody Essex Museum, the Salem Witch Museum, the House of the Seven Gables, the Salem Maritime National Historic Site, and more.
The Arnold Arboretum
The Arnold Arboretum of Harvard University is a free, beautiful park designed by Frederick Law Olmsted. This botanical garden is open daily and is the perfect place to visit in the fall.
Head of the Charles
Another annual sporting event in Boston is the Head of the Charles Regatta. This year, it will take place from October 18th through October 20nd. The race starts at the Boston University DeWolfe Boathouse, and there are various areas to watch it.
They recommend that guests take public transportation, as parking is limited. Visit their official website for tips on where to watch the regatta.
Wachusett Mountain
While the White Mountains in New Hampshire and the Green Mountains of Vermont are popular ski areas in New England, Massachusetts also has several ski resorts. Wachusett Mountain, located in Princeton, MA, is home to several popular fall festivals that are so much fun.
In the past, there have been several different options available, including BBQ Fest, Kids’ Fest, Apple Fest, Fall Food Truck Fest, and Oktoberfest. Tickets are available online and, in some cases, include a ride on the Skyride. It’s a beautiful area with lots of outdoor space.
Walden Pond
Enjoy the cooler temperatures by visiting some of Massachusetts’ outdoor attractions, like Walden Pond State Reservation (a state park). The inspiration for Henry David Thoreau’s Walden offers trails to walk around and explore.
The Big E
The Big E, the Eastern State Exposition, is similar to a State Fair. It offers amusement rides, delicious food (along with some crazy treats), live entertainment, a circus, animals, and more. In 2024, it runs from September 13th through September 29th.
As the name would suggest, the Big E is a huge event, and you can easily spend the day there. Many New Englanders visit the fair, and it’s very popular.
It’s located in Springfield, MA, so you may consider staying overnight nearby. Visit their website to learn more about the location, hours, and events. This event only runs until late September, so keep that in mind as you plan your trip.
Cape Cod
The coastal areas of Massachusetts, including Rockport (on the North Shore) and Cape Cod, are most commonly visited in the summer months. However, the fall is a beautiful time to see, and you’ll find these charming places may be best explored with fewer crowds.
Keep in mind, however, that places within these tourist areas operate seasonally, so it’s best to look online to ensure everything you want to do and see is open and operating.
One fun event is the Wellfleet Oysterfest, which will take place on October 19th and 20th this year.
The Mohawk Trail
The Mohawk Trail is a 63-mile scenic road trip through Western Massachusetts. Along this route, you’ll find beautiful views of the fall foliage, shops (including antique shops and specialty stores), state parks, museums (including the MASS MoCA in North Adams), restaurants, and more. Visit their website for the specifics and route information.
