7 Nature Trails to Explore in Chatham

Explore the outdoors this winter by taking a hike on these seven trails.

Text and photography by Joseph Porcari

Chatham is blessed with both natural and manmade riches—glorious beaches and waterways, an iconic inn and a historic Main Street lined with shops and restaurants. But there are also hidden treasures, literally steps away, in the form of walking trails that offer unspoiled views of freshwater ponds, marshlands and saltwater beaches.

The walking trails, mostly laid out as loops, average about a mile long. They are maintained by a professional land steward, devoted volunteers and nonprofit organizations. Chief among them is the Chatham Conservation Foundation (CCF), the first private land trust on Cape Cod established in 1962, dedicated to preserving habitat, water protection and promoting public enjoyment of the visual quality of the landscape. In partnership with the Town of Chatham, the CCF has almost 700 acres of land under its care.

We walk for recreation, but we also walk to experience a sense of freedom. We walk to reflect and for inspiration, and we walk to reconnect with nature. The brevity and proximity of Chatham’s walking trails enable us to make them part of a daily routine. They offer a tonic and natural remedy for our daily cares. As CCF trustee Carol Odell puts it, “Nature is cleansing.”’


Look for the beige oval CCF signs along Old Comers Road or Training Field Road marking the trail entrances. Parking is available.

The Training Field Triangle is a 39-acre oak and pine forest containing a gentle .75-mile loop trail. It derives its name from its use as a training field for the colonial militia and its shape from old cart paths. The triangle-shaped trail is surrounded by busy roads, but set back far enough to muffle any traffic sounds. The trail slopes down about 60-feet to a kettle hole wetland and certified vernal pool. The Old Comers Road side of the triangle is the site of Chatham’s smallpox cemetery dating from 1765-66. There are a few crumbling headstones—a poignant reminder of the epidemic which ravaged the town.


The entrance to the trail is on a dirt road off Route 28. Look for the oval CCF sign. Parking is available.

The 1.1-mile loop follows the eastern edge of its namesake creek and the remains of an old cranberry operation, which is gradually returning to natural wetland. There’s an upper and lower section of the trail; the lower portion parallels the brackish freshwater creek and is bordered with marsh grasses, cattails and ferns. The upland section snakes through pine and oak woodland.

Land steward Matt Cannon says this is his favorite Chatham trail. “You are able to walk along the edge of upland and see the transition of plants down to the water. The bird life is incredible. It’s a great view and a unique experience overall.”


Parking is available off Old Queen Anne Road next to the trail entrance. Look for the oval CCF signs.

The 1.25-mile Barclay’s Pond trail is laid out on land acquired by the Chatham Conservation Trust and named after the first parcel donor, William F. Barclay. Along with the adjacent town land, there is a combined 116 acres of woodland, mostly pitch pine and oak. The trail meanders over terrain ranging between 20 feet and 80 feet above sea level and diverts the walker with several side paths. It touches on three kettle hole freshwater ponds: Barclay’s Pond, Mary’s Pond and Schoolhouse Pond. These are perfect spots to observe both native and migratory water fowl. The periphery of the ponds is home to increasingly rare plants like the Plymouth gentian and insects like the damsel fly.


The entrance is located on Old Main Street. Some parking is available.

There’s an engaging .75-mile-long loop trail with three side paths in the 10-acre Sylvan Conservation Area in South Chatham. The land encompasses deep woods, open fields and 600 feet of freshwater shoreline overlooking Black Pond, and the much larger White Pond. Once operated as a nursery by the Sylvan family, and planted with ornamental gardens, there is a unique mix of native and non-native trees and plants. Pitch pines and oaks grow alongside European beech and yews, and the paths are bordered with ferns, daffodils and rhododendrons.

The Town of Chatham purchased the property in 2004 to remain as conservation land forever, and the Friends of Sylvan Gardens was established to assist the town in managing and improving the land. Plans are in the works to build an ADA compliant, compressed stone path and benches from the beginning of the trail to the pond overlook.


Parking is available along Old Comers Road next to the trail entrance sign.

This 11-acre site is home to a mix of upland and wetland species and its .75-mile loop trail follows old cart roads. A short side trail leads to the freshwater Lover’s Lake, Chatham’s only river herring spawning area, and two rustic cedar stump seats. The steep sections of the trail contribute to a good workout. Of historic interest are a few tall antennas once used as receivers for Marconi’s wireless intercontinental communications system in the early 20th century.


The entrance to the trail is just off the beach and about 100 yards from the boardwalk stairs. Parking is available at the Visitor Center and on the Morris Island Road Dike. The trail is only accessible at low tide.

Established in 1944 as an “inviolate sanctuary for migratory birds,” the Monomoy National Refuge is the site of a .75-mile walk through maritime forest, beach and tidal flats, sand dunes and salt marsh. Near the visitors’ center is a boardwalk section with overlooks framing postcard-worthy views of the Atlantic, South Beach, and North and South Monomoy Islands.

Walking from the beach through the dune and from the sand plain to the upland section, one can appreciate the complex coastal barrier ecosystem that forms the Outer Cape. You can literally see, hear and feel the wind and sea shaping the land under your feet.


Accessible only by boat, kayak or canoe; visitors may come ashore on the island’s north and west sides.

Manta-ray shaped Strong Island is the crown jewel of Chatham’s conservation lands and a vital part of the Pleasant Bay ecosystem. A major feeding area for migratory shorebirds, there are 75 acres of upland purchased by the Chatham Conservation Foundation from the Horst family and 69 acres of town-owned marsh. The island has a colorful history and was considered as the possible site of a second-term JFK summer White House.

Facing south, the 1.7-mile upland trail offers painterly views of the marsh and bay, while on the north side there’s a pristine sandy beach. Chatham resident and Skidmore student Alex Farkas kayaked to the island for the first time this summer. “I felt far away from a town buzzing with summer energy and found a peacefulness on Strong Island which was the essence of natural Cape Cod.”

There are strong currents and tides in the channel and one must exercise extreme caution. The closest town landing is at the end of Strong Island Road. There is a three-acre private reserve on the island and everyone is urged to stay on the trail, observe all signs and respect the private area.