Outdoor Recreation

The Trustees Hikers Top Ten

We asked our hiking experts their favorite places to hike

Monument Mountain

We asked the members of our Hike Trustees group to vote on their favorite Trustees hiking properties. You’ll find some of your favorites along with perhaps some undiscovered gems!


10. Monument Mountain, Great Barrington

Trustee Hiker Simone said: “Monument Mountain was my first uphill mountain hike and it was an unforgettable experience. I think it’s a “must” for anyone visiting western Massachusetts.”

From the 1,642-foot summit of this popular peak—which once drew 19th-century literary giants—gaze across the splendor of the Housatonic River Valley.

9. Coolidge Reservation, Manchester-by-the-Sea

A scenic pond and a small forest of pine and oak lead you to a spectacular seaside lawn offering memorable views of Massachusetts Bay and the North Shore.

8. deCordova Museum & Sculpture Garden, Lincoln

Trustee Hiker Pat said: “Don’t miss the creative sculptures on the grounds of the deCordova Museum in Lincoln. Some nice trails through the woods too. Bring a picnic! Make a day of it!”

The Sculpture Park occupies the entire campus: 30 acres of beautifully landscaped lawns, forests, fields, gardens, and terraces on a rolling site along the shore of Flint’s Pond in Lincoln, Massachusetts. At any given time, approximately 60 sculptures are on display in the Sculpture Park.

7. Ravenswood Park, Gloucester

Ten miles of woodland paths and trails meander through the park, providing plenty of room to picnic, bird watch, walk, cross-country ski, and simply appreciate the outdoors. Wander the child-friendly, two-mile Ledge Hill Trail among the magical-looking, fern-covered boulders, or trek to the overlook to Gloucester Harbor.

6. Noanet Woodlands, Dover

Follow a network of trails across a grand preserve that features woodlands and ponds, a former mill site, and Noanet Peak, which offers views of the Boston skyline.

Trustee Hiker Andrea said: “Clearly marked trails, lots of options, and kiosk for parking. We did the blue loop with a detour to the peak. Super nice and easy to get to from the city.”

5. Halibut Point Reservation, Rockport

Scramble across ledges scarred for eons by wind and wave, and examine tide pools teeming with marine life.

Trustee Hiker Chris: “When we go north to visit our sons and grandkids it’s definitely Ward Reservation and Halibut Point. All are perfect for a 3 generations hike.”

4. Appleton Farms, Hamilton & Ipswich

Start your visit at the white farmhouse affectionately called the “Old House,” and easily find your way to our many hiking and walking trails. Follow the paths to Sunset Hill, Wilson’s Field, Briar Hill, The Great Pasture, The Plains, and beyond. Six miles of footpaths, bridle paths, and farm roads (easy walking and great for jogging strollers), some of which are part of the Bay Circuit Trail, crisscross the farm.

Trustee Hiker Kimberly describes her Appleton Farms hike: “The cloudy skies gave way to patches of blue, with rays of sun illuminating the footpaths that meandered through the woods and plains. The pond was teeming with wildlife, and the sounds of peepers offered a sweet melody.”

3. Ward Reservation, Andover

Trustee Hiker Vanessa calls Ward Reservation “the perfect hike!”

Explore this sprawling landscape along almost 15 miles of trails and climb a hill for great views from the Merrimack Valley toward the Boston skyline.

2. World’s End, Hingham

Trek along Frederick Law Olmsted-designed carriage paths toward rolling hills and rocky shorelines, and discover sweeping views of the Boston skyline.

Trustee Hiker Sue said: “My favorite because of the different features. Cliff walks, bird watching, 3 great hills to walk over through giant fields. Great views of Boston from the top, and fantastic sunsets.”

1.  Crane Beach, Ipswich

Trustee Hiker Kristin said: “Crane Beach is one of my favorite places in the state – every time I go there and hit the top of the stairs and see the ocean again, I feel something in myself unknot. It happens regardless of the time of day, time of year, kind of weather. I breathe better.”

Experience 5.5 miles of trails, traversing the dunes, maritime scrub forest, and beachfront on both the Ipswich Bay and Essex River estuary sides of the Castle Neck peninsula. Due to soft sand and many hilly dunes, trail difficulty is moderate.