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Guided Tour of Martha's Vineyard

Guided Tour of Martha’s Vineyard
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For years, we had to break the law to walk Menemsha Hills. This Trustees of Reservations property was marooned: open to Vineyard Sound on the shore, but no-trespassing signs on private land making it inaccessible from the road. Going there in the spring or fall, we rarely saw another soul and joked that we’d gladly risk jail time for this spectacular walk.

Since then, nearby landowners have donated easements; walking Menemsha Hills will no longer make you a criminal. Which meant that when I planned a walk last summer with my sister-in-law and niece, I was afraid we might be just a few among a crowd.

Happily, we were one of only four cars in the parking lot and saw only a few other walkers. It’s just big enough (211 acres) and lush enough (lots of tall trees) to hide anyone who might be there, and just long enough (three-plus miles) to deter short-strollers.

Thousands of years of glacier activity bulldozed its way through what’s now Vineyard Sound, endowing the north shore with multiple ecosystems. It’s the contrasts in Menemsha Hills that make it one of my favorite walking trails: wetlands to dry dune grass; sea level to high peaks (high for the Vineyard, that is); dark, close forest to bright, wide-open horizon.

My niece ran skipping along sandy paths crowded by pitch pine, under maples, beeches, and oaks, and up the slope of Prospect Hill (the island’s second highest peak, at a towering 308 feet). Then down we followed her into a bosky dell, where she sat for a while in the crook of a spooky gnarled tree, dangling her legs above a fern glade that might have made us think we were in New Zealand. We rounded a bend and out into the light we came, up a rise to a bluff overlooking hills of goldenrod and beach plums, rolling down to the sea, where in the distance, the Elizabeth Islands lay out in a line.

We climbed down stairs to a rocky beach where once, long ago, Menemsha’s brickworks stood; you’ll still find bricks scattered among the beach stones. Needless to say, the beach isn’t your typical sandy strand, but with a boogie board, you could get into the water here, then lay yourself out on a boulder to dry like a seal.
We ate apples and peanuts, let the water spray our faces, smiled at two other people sharing a seat on a boulder. Then we headed back up the stairs through incoming fog, back through the enchanted forest, and home to tell our families about our magical day, right in our own backyard, hidden in plain sight from everyone else.

Trail map at:

Finding Your Inner Robinson Crusoe on a Long Chappy Walk

Thomas Hart Benton, the famous American regionalist artist, spent his summers painting at a simple beach house in Chilmark. He once said that when he stood at the edge of the sand cliffs, surveying the south shore of Martha’s Vineyard stretching out on either side of him, it was like “standing on the edge of a big cereal bowl.”

The far eastern edge of the bowl would be Chappaquiddick Island, which until a few years ago was connected to Martha’s Vineyard by a spit of sand at Norton Point just wide enough to drive (at low tide), and wide enough to walk–meaning, you could have walked, if you’d wanted to, the entire cereal-bowl south shore of Martha’s Vineyard, from Gay Head (Aquinnah) in the west to Wasque Point on Chappy,a distance of about 19 miles.

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

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