Hiking through beauty: The most picturesque hikes on Martha’s Vineyard

Martha’s Vineyard truly is is a nature lover’s paradise. With endless stretches of scenic shoreline, rolling hills, expansive woodlands, and hundreds of miles of protected trails through the Island’s diverse landscape, there really is no better place to take a hike. From the more casual strolls along the streets of Oak Bluffs to the more challenging routes up-Island here’s our picks for the most picturesque (and most Instagrammable!) places to explore on foot.

Photo: Nicole Friedler

Aquinnah Headlands Preserve
This area refers to what is commonly known as the Aquinnah or Gay Head Cliffs, the most majestic, and most visited location in all of Martha’s Vineyard. This spot is often named the most beautiful location in Massachusetts and for good reason. This sacred ground covers almost 50 acres and the Cliffs themselves rise 100 feet above the Atlantic Ocean. Enjoy views of the Elizabeth Islands, a little known chain of Islands north of Martha’s Vineyard, as well as the Buzzards Bay coastline, the Rhode Island shore, and, directly below, the Devil’s Bridge, a mile-long string of boulders and other glacial shards that proved dangerous to many in maritime history over the years. The property is managed by the Land Bank and also includes Moshup Beach a nearly half mile stretch of expansive coastline situated under the clay cliffs.

Thimble Farm
​This impressive cropland has long been a fixture on the Island, and was originally a dairy farm for over 300 years. Today it’s known for its innovative hydroponic greenhouses, one of which measures 31,000 feet. The Land Bank purchased the land’s development rights, plus a circumferential trail leading past Little Duarte’s Pond, a thick cool wetland nearby, on a preserve of over 60 acres. Explore this area and appreciate the inner workings of one of our most powerful farms, which acts as the Island Grown Schools’ Farm Hub, as well as a beacon of natural and agricultural beauty. 

Photo: Max Bossman

Mytoi Japanese Garden
​If you weren’t expecting it you’d be surprised to find this little slice of Japanese heaven tucked away on Chappaquiddick Island, a small island off of Edgartown. Mytoi is an intimate Japanese-style garden, which offers a natural place to escape and ponder. Sheltered by a charming cluster of pines, the preserve includes a small pond and island, flowers and plants, walkways and seating areas perfect for contemplation. If you’re looking for an outdoor venue quiet reflection or meditation this is the spot. 

Photo: Aela Mass

Caroline Tuthill Preserve
​This parcel of land is conveniently located off of Beach Road in Edgartown and Edgartown-West Tisbury Road. Many locals have driven past it hundreds of times without giving it second thought but it deserves to be a destination in its own right. Managed by Sheriffs Meadow Foundation this 150 acre preserve is made up of oak and pitch pine forest, wooded wetlands, salt marsh and open meadow, and it abuts Sengekontacket Pond to the north. According to Sheriffs Meadow Foundation while walking the preserve one might observe such birds as crows, blue jays, chickadees, towhees, pine warblers, white-breasted nuthatches and red-eyed vireos. In spring, one may also be treated to the sight of lady’s slippers, which grow along the trail and at the foot of the Preserve’s many oaks.

Menemsha Hills Reservation
Menemsha Hills is a beautiful and diverse nature reserve located off of North Road in Chilmark. Menemsha Hills is a popular hike that offers a variety of natural habitats including wetland, marsh, wooded groves, and a rocky shoreline, with sweeping views of Vineyard Sound. The three miles of trails are easily passable for the moderate hiker, with some extra energy needed to summit Prospect Hill, the second highest point on the Vineyard at 308 feet, and the view is worth the extra work!
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For additional details on our locals hikes visit the websites of the Martha’s Vineyard Land Bank and the Sheriff’s Meadow Foundation. Also be sure to download this handy trail map, along with TrailsMV, a user friendly iOS app that helps you better explore and connect the various trails on Martha’s Vineyard. Happy hiking!