UPDATED for 2020! With the longer days and warmer temperatures of summer in front of us, it is the perfect opportunity to get outside and enjoy the beautiful weather. With so many walking & nature trails from Boston to Cape Cod at our doorstep, our agents have selected 30 of their favorites. Try a new one every day or discover new off-shoots from an old favorite!

Nature Trails from Boston to Cape Cod

Greater Boston

Fresh Pond | Cambridge
Fresh Pond Reservation consists of 162 acres of open space surrounding and protecting the 155 acre Fresh Pond Reservoir. Agent Louise Olson recommends the route for dog walkers, joggers & families.

Minuteman Bikeway | Lexington, Bedford, Arlington, Cambridge
The Minuteman Bikeway passes through the historic cities where the American Revolution began in April 1775. View the 10-mile trail map here. 

Deer Island Trail | Boston, Winthrop
Offering fabulous views of the Boston Skyline, Deer Island is a 2.7 mile loop trail for all skill levels.

Blue Hills Reservation | Quincy, Canton, Milton, Braintree, Dedham
With more than 125 miles of trails through forests, wetlands and hills – there is always something new to see! View suggested hiking loops.

Noanet Woodland | Dover
With tons of trails and a view of Boston from the top, Noanet Woodlands is easily one of the best go-to spots.

Rocky Narrows | Sherborn
Enjoy views of the Charles River as you make your way through 7 miles of trails set amidst pine groves and wetlands.

Medfield Charles River State Reservation | Medfield
Surrounding the shut down Medfield State Hospital (used to film Shutter Island and other movies), the Medfield Charles River State Reservation 3.7 mile loop allows users to walk around the boarded up buildings of the hospital grounds.

South Coast

Sippican Lands Trust | Marion
Celebrating their 45th anniversary, the Sippican Lands Trust has several walking trails on donated land throughout Marion.  Currently, the SLT protects 1,350 acres of open space. See all of their properties with trails here.

Demarest Lloyd State Park | Dartmouth
At Demarest Lloyd, an 1800-foot saltwater beach is backed by rambling hills of beach grass and shaded, grassy picnic sites. A broad, scenic marsh lines the Slocum River on the park’s eastern edge.

Flora B. Peirce Nature Trail | New Bedford

The Flora B. Peirce Nature Trail has new boardwalks and amenities to enhance your experience. The trails are approximately 1 mile long and will take you past a certified vernal pool, a pond, the head of the Paskamansett River and various forest habitats supporting a variety of wild life. Located off New Plainville Rd with parking on Falmouth St.

William Minot Forest | Wareham

Located next to Minot Forest Elementary School and several neighborhoods, William Minot Forest  is a convenient place to take a stroll. Make your way through 200 acres of hilly pine and oak woods while listening for songbirds. There is a network of trails that you can mix and match to meet your preference — from a short loop trail to a several mile trek.

East Over Reservation | Marion, Rochester 
Miles of trails pass through a mosaic of agricultural fields, successional forests, and winding hedgerows all surrounded by quarry-stone capped double walls. A new trailhead on County Road in Marion now lets you access miles of East Over landscape.

Cape Cod

Upper Cape

Heritage Museums & Gardens | Sandwich
Unbeknownst to many visitors, the full-extent of Heritages’ 65 acres of developed garden is open to the public. This includes several miles of nature trails. While you make your way through the gardens and galleries, keep an eye out for the meandering trails that diverge from the main loop.

Beebee Woods | Falmouth
Beebe Woods Loop is a 3.1 mile moderately trafficked loop trail located near Woods Hole, Massachusetts that features beautiful wild flowers and is good for all skill levels.

Salt Pond | Falmouth 
Part of the Salt Pond Areas Bird Sanctuaries, this 41 acre parcel has wonderful nature trails. Download the trail map.

Lowell Holly Reservation Trails | Mashpee
2.4 mile loop trail that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round.

Washburn Island – Waquoit Bay Nat’l | Waquoit
Washburn Island is one of the last large undeveloped coastal properties on Cape Cod and a jewel within the Waquoit Bay Reserve. Washburn Island is one of many trails that is part of the Waquoit Bay Reserve.

Mid Cape 

Eagle Pond Sanctuary | Cotuit
Part of the Barnstable Land Trust, the sanctuary is a popular walking path, dog friendly, and comprised of various habitats such as upland pine forest, a pond with a mile-plus loop trail, a cedar swamp and a maple swamp, and more.

Crowes Pasture | East Dennis
This 138-acre development provides panoramic views of Cape Cod Bay and Cole’s Pond. There is a trail with parking available at the main parking lot at the entrance to Crowes Pasture.

Long Pasture Wildlife Sanctuary | Osterville
Gentle, varied trails lead to what some have called a “million dollar view,” with Barnstable Harbor flanked by the dunes of Sandy Neck Barrier Beach. Download the Long Pasture Trail Map.

Barnstable Great Marsh | Barnstable
Barnstable Great Marsh is an integral part of the ecologically significant 3,800-acre Sandy Neck salt marsh and barrier beach system. Along with the expansive salt marsh views, the sanctuary features two open ponds, shady oak woodlands, and numerous wildlife. View a trail map.

Callery-Darling Conservation Area
This trail is located north of Route 6A and stretches from Homers Dock Road to the salt marshes west of Center Street. The Bass Hole Boardwalk is one of the more popular attractions within the area. Download trail maps from the town of Yarmouth here.

Lower & Outer Cape

Nickerson State Park | Brewster
There’s no shortage of trails to explore as you make your way through Nickerson’s 1900 acres. 
Want to spend the night? Learn more about camping at Nickerson.

Kent’s Point | Orleans
Kent’s Point contains more than a mile of undeveloped shoreline, and fronts on Lonnie’s Pond, Little Pleasant Bay and Frost Fish Creek. The main trail goes up the center of the property leading to a boardwalk overlooking The River and the northern portion of Pleasant Bay.

Cape Cod National Seashore Trails | Lower & Outer Cape
The National Seashore has 17 walking trails to choose from including Great Island Trail, Atlantic White Cedar Swamp, The Province Lands Trail, Beech Forest Trail and many more!  See a full list of trails here.

Cape Cod Rail Trail | Dennis, Harwich, Brewster, Orleans, Eastham & Wellfleet 
Often known primarily as a biking trail, the Cape Cod Rail Trail also caters to walkers and joggers. Make your way through 6 Cape Cod towns along this 22-mile trail.

Thompson’s Field Conservation Area | Harwich
Thompson’s Fields 54 acres were purchased for preservation by the town of Harwich in 1984. Today, the 2.75 mile trail is a popular spot for dog walkers.

D. Isabel Smith Monomoy River Conservation Lands | East Harwich
The Wequassett Resort was very instrumental in procuring the funds to buy these last 42 contiguous acres in Harwich on the Monomoy River.

Punkhorn Parklands | Brewster
Punkhorn Parklands provides a plethora of opportunities for passive recreation including an extensive trail system that offers visitors the prospect of exploring the full richness of the natural wonders of Brewster. Download the full trail map.

Wellfleet Bay Wildlife Sanctuary | Wellfleet

Wellfleet Bay provides peace and unmatched beauty on the hillsides and shoreline overlooking Wellfleet Harbor. Extensive trails bring you to a panoramic salt marsh, sandy barrier beach, and pine woodlands, each attracting a wide array of wildlife.