Take a Hike: 100 Trails on Martha’s Vineyard

Take a Hike: 100 Trails on Martha’s Vineyard

December 29, 2018

Nature is not overrated. Whatever you do, don’t leave the Vineyard without a walk along one of dozens of trails that crisscross the Island. It’s true that the Vineyard doesn’t have mountains; so technically what we do on on the Island is walking, not hiking. But what we  lack in challenging terrain, we make up in sheer beauty – and abundance. There are over 100 walking trails open to the public on the Island; most of them are maintained by one of four organizations – the Martha’s Vineyard Land Bank, Sheriff’s Meadow Foundation, The Trustees of Reservations, and Mass Audubon. With this network, it’s possible to explore every kind of coastal ecosystem, from sandplains to pine barrens, on foot. But if time is short, pick one of our five favorites featured below.


Menemsha Hills, Trustees of Reservations.

Winding down to the rocky shore, the trail through Menemsha Hills Reservation in Chilmark is a descent through a changing landscape that begins with a magical forest and ends with grassy dunes. Along the way, you might be tempted to climb a tree or look for fairies, but you’ll definitely want to stop to see the unfolding view of Vineyard Sound. Just a short way into the trail, take the spur up to Prospect Hill, the second highest point on the Island, and look out at the Elizabeth Islands on the horizon. Near the bottom of the trail is an observation platform where you can spy an old brick chimney, the remains of a 19th-century brick factory. Be sure to continue down to the beach, but reserve some energy for the walk back up.


Looking for a picture perfect trail? Cedar Tree Neck Sanctuary in West Tisbury has inspired Island painters from Allen Whiting to Kenneth Vincent. Shaped by the salted winds, the stunted American beeches are living sculptures. The 400-acre sanctuary is divided into several trails; take the red trail for an easy hike through the woods down to the beach. Swimming isn’t allowed (nor are dogs) but the beach is ideal for strolling.



For a flat, accessible trail, explore Sepiessa Point Reservation on the south shore of the Island in West Tisbury. The trail begins with a shady walk through a wooded area, but leads to the shores of Tisbury Great Pond beyond an open field of grasses, restored to serve as a foraging habitat for hawks and owls. The pond is open to swimmers, but be sure to wear shoes to protect from sharp oyster shells. Sepiessa also has a boat and canoe launch, and the pond is a good spot to catch crabs. Fido is welcome to come along on your Sepiessa adventure as long as he or she is on a leash.


The four miles of trails curving through Felix Neck Wildlife Sanctuary – and around the shores of Sengekontacket Pond – are ideal for families with small children, and are also a good choice for nature lovers. (There is a one-mile universally accessible trail.) The trails come and go from the shores of the pond; keep a lookout for otter slides, birds’ nests, and other signs of critters. Felix Neck (located in Edgartown) is truly an outdoor classroom, but remember to leave everything as you found it; take only pictures. Felix Neck costs $4 for Mass Audubon non-members.


Wander the wilds of Waskosim’s Rock Reservation on a gray day – it has a lovely, eerie solitude that is best explored when the weather matches the mood. This property in West Tisbury is wooded to the south with open fields in the middle and wetlands flanking Mill Brook to the north. For history buffs, there are the remnants of the 17th-century homestead of James Allen. Then there is the rock itself. Looking like a great whale head erupting from the ground, the rock has a written history dating to the 1600s, when it marked the line between the Wampanoags’ land and the land white settlers claimed for themselves. These days, adventurous types can scrabble up the rock, using the long crack running down it as a foothold.


Swim, Hike, or Kayak At the 600-acre Long Point Wildlife Refuge on the south side of the Island. With a long woodland trail, an oceanfront beach, an accessible pond, and a variety of vegetation, Long Point has something for everyone. If the beach is your destination, be sure to hit the parking lot early in the day before it fills up. The trails, which are an easy walk through both woods and sandy, open areas, are a compelling destination during the off-season.


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