Menemsha Hills Reservation

This is my favorite spot on the island. It’s an amazing winding trail (about 3.5 miles total, some minor hills, and some stairs along the way) that leads to an absolutely spectacular rocky beach — there are really no words for the beauty of the vista here. The other plus is that Menemsha Hills is almost always empty — in all the times I’ve been there, I’ve never seen more than two or three other people out there, and I’m grateful for the solitude, the breath of fresh air from the crowds, and the beauty. Check this place out.

A
hidden
jewel
Prospect Hill in Menemsha Hills is either the highest or second highest point on the Vineyard. I’m not sure because I have heard both. It’s only 300 feet high, yep it’s not exactly a mountain but since the whole island is basically a glacial moraine, not bad. Heard all kinds of tales about people putting dirt and rocks on the top to keep it the highest point. As with most island tales I am somewhat skeptical but there are a bunch of boulders on the summit that do look like someone took the trouble to move them there.
The entire reservation is over 200 acres and a absolutely fantastic place to hike. Anyone interesting in nature will love this place, ancient oaks, cherry trees, maples and a lot of shrubs and plants with names I’m not familiar with. Plus tons of obvious glacial evidence and debris.
The whole trail is probably a little over four miles but with a lot of ups and downs. Two hills to negotiate and lots of curves and rocks to go over. Not very many flat places so the four miles is longer than it seems. Bring tick repellent because the nasty little things always seem to appreciate cool places like this.
At the eastern most part of the trail you arrive at the magnificent Great Sands Cliffs, with incredible views in every direction. You can then climb or more likely slide down the slope to the beach. A great place to swim if you respect the water and don’t get yourself killed.
Menemsha Reservation and Prospect Hill are hidden jewels, even in the busy tourist season virtually no one goes here. The best places on the island always seem to be the ones least frequented.