The 5 Best Outdoorsy Towns to Explore in Massachusetts

Massachusetts may be one of the smaller states in our country, but when it comes to outdoor recreation, the Bay State really packs a punch. From beautiful beaches to scenic mountain trails and peaceful lakes, you really can experience it all within our 10,554 square miles. And best of all, you don’t have to drive far to set out on an incredible adventure in nature. But if you are unsure of where to go, check out my list of the best outdoorsy towns in Massachusetts.  

1. Great Barrington, Massachusetts

The Berkshires region is one of my favorite New England outdoor recreation spots. The scenery is simply breathtaking, and there is just so much to experience. The Berkshires town of Great Barrington is a year-round nature lover's dream. Known as one of the best outdoor destinations in Massachusetts, this picturesque community offers a little bit of everything. During the warmer months, stunning Monument Mountain and the universally accessible Housatonic River Walk are popular places to hike, and local Lake Mansfield Recreation Area offers a refreshing respite from the summer heat. Come back and visit in the winter, and you can enjoy skiing, snowboarding, and tubing at Ski Butternut.

2. Provincetown, Massachusetts

If you prefer a little beachside recreation, Provincetown is the place to go. Swim, boat, or fish in the lovely Cape waters or just spend the day relaxing on the sandy shores of Provincetown’s four scenic beaches. You will also discover opportunities for hiking, biking, and whale watching. And if your idea of outdoor recreation is simply enjoying a great meal or a yummy cocktail on a waterfront deck, just visit the Red Inn Restaurant and sit back and enjoy the view.

3. Princeton, Massachusetts

Princeton is another local spot that offers a variety of activities for every type of outdoor enthusiast. Mount Wachusett is the town’s most well-known natural attraction. This beautiful mountain has miles of hiking, skiing, and snowboarding trails for all abilities. And you can find even more trails, birdwatching, and outdoor fun in Princeton at the Wachusett Meadow Wildlife Sanctuary. 

4. Charlemont, Massachusetts

If you are searching for one of the best adventure towns in Massachusetts, you should definitely plan to visit Charlemont. In this western Berkshires community, you will find fantastic Mohawk Trail hiking, as well as endless opportunities for ziplining, skiing, kayaking, and whitewater rafting. Charlemont is also home to the Thunderbolt Mountain Coaster, a one-of-a-kind forest alpine coaster that should be on the top of any adventure bucket list.

5. Mount Washington, Massachusetts

This list of small towns in Massachusetts for nature lovers wouldn’t be complete without a mention of a local cascade. Bash Bish Falls in remote Mount Washington is the state’s highest single-drop fall and is a must-see for any waterfall chaser. For some incredible panoramic views, you can also head to the summit of Mount Washington's Mount Everett State Reservation, which is part of the Appalachian Trail.  

With all of these amazing local recreation opportunities, it may be hard to choose a favorite nature town in Massachusetts. And you really don’t have to make that decision; simply visit as many as possible. And if you are looking for even more outdoorsy spots beyond this list, I suggest visiting these fantastic Massachusetts state parks.