5 Great Hiking Trails on Martha's Vineyard for Fall & Winter

5 Great Hiking Trails on Martha's Vineyard for Fall & Winter


Hike No. 1: Great Rock Bight, off North Road, Chilmark

This time of year is a spectacular time for hiking on Martha’s Vineyard. With dozens of trails that wind through the woods, along ocean fronts, and over bluffs, hiking on-Island is not your average hiking. And with foliage peeking later on the season than on the mainland, now is the perfect time to enjoy the trails.

1. Great Rock Bight, Chilmark: A popular trail off of North Road in Chilmark, this hike takes you a few moderately easy miles through the woods and to an incredible bluff overlooking Vineyard Sound. Its beach is only accessible by the foot path, so even during the summer, it’s never crowded. Trails are dog-friendly, so bring your pooch along!


_Longpoint Wildlife Refuge: Beach and woodland formed by the last ice age.


2. Long Point Wildlife Refuge, West Tisbury: One of the most magical places on Martha’s Vineyard, Long Point Wildlife Refuge has miles of hiking trails with some of the most pristine vistas and vegetation.

At more than 600 acres, Long Point encompasses beach, dune, and woodland, which bracket a broad sandplain heath. The property is an off-season treasure, especially for birders and other nature-watchers.

Long Point Wildlife Refuge is all that remains of a broad prairie with scattered woods that was formed over many years after the last ice age.  You can stay by the water to swim and relax, or follow a two-mile trail that leads through oak forest and savanna bordered by Middle Point, Long Cove, and Tisbury Great Ponds. Sorry, dogs not allowed.


Caroline Tuthill Preserve: Dogs are welcome.

3. Caroline Tuthill Preserve, Edgartown: This fun trail is a favorite among Islanders. It’s easy to get to, just off of Edgartown-Vineyard Haven Road, and the winding trails take you over small hills, through the woods, and to beautiful water views of Sengekontacket Pond — just a few easy miles will get you there!

And if you bring your dog, she’ll likely enjoy a playdate while there since this trail is a favorite among dog owners. Be sure to also check out the many other trails across the Island that are part of the Sheriff’s Meadow Foundation.

4. Menemsha Hills, Menemsha: This 211-acre preserve allows hikers to climb to the top of the second-highest point on Martha’s Vineyard, and offers spectacular ocean views. Three miles of trails cover wetlands, woodland groves, open coastal plain, and a rocky ocean edge.

Approaching the shore, dune grass and pitch pine predominate. Hikers will also see goldenrod and beach plum helping anchor the dune cliffs above the beach, where rocks of every size dot the sand and line tide pools.

And just beyond the northeast edge stands the remnants of a brick chimney, all that remains of a 19th-century brickworks. Please leave dogs home. Visit The Trustees of Reservations for more info about all their hiking trails.


John Presbury Norton Farm, the start of 4 miles of trails over 118 acres.

5. John Presbury Norton Farm to Womesket Preserve: A memorable place to hike in any season — and a fabulous place of more than 118 acres to snowshoe or cross-country ski during the winter.  John Presbury Norton Farm’s trails bring hikers to the lovely Wompesket Preserve. Start at the intersection of the State and Old County Roads and follow a continuous public trail of some four miles in length from Duarte’s Pond on the Lambert’s Cove Road to the Old County Arboretum opposite the town school.

This combo is home to easy hiking trails that meander through the woods, across open fields, and eventually to Blackwater Pond (where, if you’re feeling extra adventurous, you can pick up more trails and continue on). And dogs are always welcome! Be sure to check out Martha’s Vineyard Land Bank for all of their trails.

Source: Martha's Vineyard Chamber of Commerce

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