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Ways to Enjoy the Fall in Massachusetts

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.

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.

Pumpkins to pick

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 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 orchards

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 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.

Orange tree in the fall

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.

There’s also Sauchuk’s Corn Maze and Pumpkin Patch located in Plympton, MA. Purchase tickets in advance to make sure you get in.

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 do your own harvesting.

Benson’s Pond, located in South Middleboro, MA, offers small groups the opportunity to be cranberry bogger 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.

Salem in October

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. After a year off last year, Salem is back to offering their Haunted Happenings event with activities every day of October.

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 so much more. Visit their website for full details on what events will be offered.

While you are 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 was designed by Frederick Law Olmsted. This botanical garden is open daily and is the perfect place to visit in the fall.

Boston Marathon

The Boston Marathon typically takes place on Patriot’s Day in April of every year. For Bostonians, it’s the unofficial start to the spring. Unfortunately, due to the pandemic, the Boston Marathon was pushed to Monday, October 11, 2021.

Spectators and families of the athletes gather along the full marathon course to cheer on all of the athletes who participate in the race. Keep in mind that there are some road closures during the race, so you’ll want to plan out your trip. Even if you aren’t watching the race, it could impact your travels that day.

Head of the Charles

Another annual sporting event in Boston is the Head of the Charles regatta. This year, it takes place from October 22nd through October 24th. The race starts at the Boston University DeWolfe Boathouse, and there are various areas to watch.

They do recommend that guests take public transportation as parking is fairly limited. Visit their official website for tips on where to watch the regatta.

Wachusett Mountain in early fall

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.

This year, there are several different options including BBQ Fest, Kids’ Fest, Apple Fest, Fall Food Truck Fest, and Oktoberfest. Tickets are available online and in some cases will include a ride on the Skyride. It’s a beautiful area with lots of outdoor space.

Walden Pond

Take advantage of 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 where you can 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 so much more. In 2021, it runs from September 17th through October 3rd.

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 find out more about the location, hours, and events. This event does only run until early October, 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 visit, and you’ll find that these charming places may even be best explored with fewer crowds.

Keep in mind, however, that places within these tourist areas do operate seasonally, so it’s best to look online to make sure everything that you want to do and see is open and operating.

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.

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