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The descent from Prospect Hill leads to a private, dirt road that divides the property. The soil underneath turns to sand, and the trees—now hollies and scrub oak—turn shorter and barer. On the approach to the shoreline at Great Sand Bank Overlook, the trees retreat from sunshine that’s easily 10 degrees warmer than the shade. It’s a short stroll through the valley and dune grass to reach the end of the trail, the sounds of footsteps turning from the quiet crush of sand to a thump over a wooden staircase during the descent.

The loose cobblestones of the beach below stretch for three-quarters of a mile. Crumbling cliff faces rise from the shoreline and expose shades of white and red from the clay underneath. Offshore, the cool blue of Vineyard Sound ripples against a cluster of submerged boulders. It’s a sport fishermen’s paradise—lobsters wash ashore after storms, trout are just a short walk to Roaring Brook, and it’s easy to land stripers in the autumn. This beach is also the most elusive summer rarity on the Vineyard: waterfront real estate, free and open to the public, virtually absent of crowds. R. Cheek

Of the many thousands that visit Menemsha Hills each year, most come in the fall. Typically, Kennedy says, these are year-rounders drawn to the foliage, the droves of monarch butterflies that flutter through, and the chance to take a deep breath after another summer season. In other words, autumn is for those familiar with the secrets of Menemsha Hills. For the uninitiated, there’s no better time to get acquainted than the present.

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Jeff is the Managing Editor for Cape Cod Life Publications.

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