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Best Ways to Enjoy the Fall in Massachusetts

Massachusetts is a popular summer destination, 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. Here are some of our favorite ways to enjoy the fall in Massachusetts.

Learn About History By Walking the Freedom Trail

Statue of man on a horse in a park surrounded by greenery
Image Credit: Jodi Grundig/Family Travel Magazine

Massachusetts, especially Boston, offers many different ways to learn about history. Take advantage of the cooler temperatures and walk the Freedom Trail in downtown Boston. You can explore the trail on your own or book a walking tour. The Freedom Trail has sixteen official sites, including the Boston Common, Old North Church, and the USS Constitution. While in Boston, you can also visit the Public Garden, Newbury Street, and Faneuil Hall.

Apple Picking/ Pumpkin Picking

Pumpkins in a field
Image Credit: Jodi Grundig/Family Travel Magazine

Apple and pumpkin picking are must-do fall activities in Massachusetts; luckily, there are many farms to visit. Check their schedules before leaving because sometimes picking is done for the day/season. In addition, some of the farms require reservations. Many of these farms are in small towns, and you’ll see some of the fall colors and beautiful scenery while taking the scenic drive.

Leaf Peeping

Fall foliage surrounded by a pond
Image Credit: Jodi Grundig/Family Travel Magazine

Peak foliage season usually happens in late October, but leaves change earlier when the temperatures get cooler. There are many places to drive around town to see leaves, although my favorite option is a day trip to New Hampshire, where the leaves on the mountains are gorgeous. In my opinion, it’s the best fall foliage.

Visit Salem, MA

Candlelight Ghost Tour booth
Image Credit: Jodi Grundig/Family Travel Magazine

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, which has activities every day of October. It’s one of the best things to do to celebrate Halloween.

Wachusett Mountain

Body of water at the base of Wachusett Mountain
Image Credit: Jodi Grundig/Family Travel Magazine

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.

Cape Cod

Boardwalk over marsh at sunset
Image Credit: Jodi Grundig/Family Travel Magazine

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.

Plimoth Patuxet Museums

Pinecones and sticks on the ground
Image Credit: Jodi Grundig/Family Travel Magazine

Fall is a great time to visit Plymouth, MA, known as America’s Hometown. Plimoth Patuxet is where you can learn about the Plymouth settlement and the Wampanoag homeland. Skip Plymouth Rock, which is much less impressive than you’d expect.

Other Things

Orange leaves on tree
Image Credit: Jodi Grundig/Family Travel Magazine

Other popular fall activities in Massachusetts include finding your way through corn mazes, touring the Mohawk Trail, attending the Big E, visiting Walden Pond, and more. Visit our blog post to learn more.

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