With 450,000 acres of protected land, waterways and historical sites, the Massachusetts park system is one of the largest in the U.S. Beyond that, even more acreage is protected by organizations like the Trustees of Reservations, making for some stellar camping and glamping opportunities. From the windswept beaches of Cape Cod to the rolling green hills of the Berkshires to the eclectic lands of Pioneer Valley, there’s an outdoor playground—and Tentrr site—for all tastes in this state.
With rolling green hills and the bulk of the state’s fresh water, western Massachusetts is the adventure capital of New England, and the Berkshires are the crown jewel. Take your pick of Tentrr campsites in this region, then head out in any direction for outdoorsy activities of pretty much all varieties: hiking, biking, class I-IV rafting, kayaking, swimming, paddle boarding, lazy river tubing with drink in hand, horseback riding, ziplining…and even falconry.
One of the many highlights is the iconic hike up Monument Mountain to Squaw Peak for views of four states. Camp near Southfield to access the trailhead. Historical fun fact: Buddies Nathaniel Hawthorne and Herman Melville often walked here, taking wine breaks in caves during rainy spells. Other popular activities include hiking sections of the Appalachian Trail—Mt. Greylock in the north and Mt. Race in the south are particularly scenic—and Bash Bish Falls.
After all this sportiness (go, you!), reward yourself in one of the area’s charming towns with a farm-sourced dinner, and make sure it includes fresh cheese and artisanal bread…plus a flight of craft beers to wash it all down, of course. And if you’re near Lenox in the summer, stretch out on the lawn of the famed Tanglewood Music Center for a concert under the stars by the Boston Symphony Orchestra to top off this vacation to remember.
The combination of mountains, farmland and universities in this region translates to nature with a cultural edge—it’s the best of both worlds. On the natural side, the rugged Seven Sisters hike (near the Westhampton campsite) in the Holyoke Range offers brilliant views along its cliffs. For cyclers, a network of bikeways traverses through the varied landscapes, with plenty of opportunities for craft beer and ice cream breaks. For road trippers, the Mohawk Trail, the nation’s first scenic byway, begins near Greenfield and stretches for 63 miles across 50,000 acres of state forest, parks and reservations. It’s also one of New England’s premier leaf-peeping destinations.
Meanwhile, get your cultural fix in the area’s many museums, including one devoted to hometown hero Dr. Seuss. Finding fresh local fare is as easy—and fantastic as their—pie with the abundance of farms and restaurants, along with craft breweries and small wineries. For extra credit, if your timing is right, visiting The Big E, New England’s mega state fair in Springfield, is a must. It features the best (and some might say the quirkiest) bits of all six states and runs for 17 days each fall.
This is where you’ll find drool-worthy scenery and cuisine all in one place. We’re talking white-sand beaches anchored by fluttering sea grass and quaint towns serving up fresh-off-the-boat seafood and homemade ice cream. Base yourself at Tentrr’s Sandwich campsite for easy access to the area’s highlights. To immerse yourself in nature, walk among the sand dunes on the 40-mile Cape Cod National Seashore trail, taking in Atlantic white cedar woodlands and migratory-bird nesting areas on the way, or two-wheel it through picturesque towns along the Cape Cod Rail Trail.
Farther afield, there’s no shortage of day-trip options, including whale watching at Stellwagen Bank Sanctuary (top ten in the world!) and following in the (dune-erased) footsteps of Eugene O’Neill and other creative types to the far end of the cape for inspiration. Martha’s Vineyard and Nantucket also beckon with their laid-back vibes, iconic gray-shingled houses, historic lighthouses and pristine shorelines.