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    Tupancy Links

    4.0 (1 review)

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    Menemsha Hills Reservation

    Menemsha Hills Reservation

    (3 reviews)

    Before our visit to Martha's Vineyard, I did a little research on-line to determine what is worth…read moredoing during our 4-day stay. Hiking and biking are our main activities, with possibly a day of kayaking thrown in. I decided that one day of hiking would consist of hiking both the Great Rock Bight and the Menemsha Hills Reservation. I wish I had put as much time and effort into researching HOW to do the hikes as I did in selecting which hikes to do, as these trails are not so easy to find. We asked at our hotel (Pequot) for maps of hiking trails and found that they didn't have any. I drove west on N Road assuming that there would be signs for these popular hiking trails, but there were none. We made it all the way to the Menemsha Beach and parked. As we knew that the hiking trail ends at the beach, we figured it would be just as nice of a hike to start at the beach and end on the hilltop. There is a Texaco Station across the road from the end of the hiking trail and I asked them for a trail map. Can you believe not only did they not have maps, they didn't know about the hiking trail or so they said. So we winged it and began hiking from the statue of the man spearing a swordfish across the marsh and up the hill until we somehow lost the unmarked trail. We eventually came out to N Road and asked several people until we finally got lucky and asked a local on a bicycle. He directed us to take Prospect Hill Road saying it leads to the hill and the trail to the beach. We never would have guessed because of the signs that said "private property" and "no trespassing". Apparently the locals want to discourage the tourists enjoyment of this natural beauty. Once on this road we never saw any signs in English for trails, but we did see one tree that had a series of trail markers, which were useless without a map showing the key. We hiked all the way to Gosnold's Way as far as we could go. We saw some trails meandering here or there off the road, but none seemed to call to us, "this must be it". So we turned back toward N Road. Less than a quarter of a mile before we reached N Road, we noticed a steep incline on our right leading to a hilltop. It turned out to be Prospect Hill which is one of the highlights of this trail. We had unwittingly hiked miles past it. There were no signs, just one lonely bench at the summit. We rest there an hour or so and then retraced our steps back to the beach. As for beauty, the place is excellent. But the only signs are to discourage rather than help hikers. Plus I don't recall seeing anyplace on Prospect Hill Road or Gosnold's Way you can park. If you do this hike I strongly advise you to do your homework.

    A hidden jewel…read more 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.

    Indian Lands Conservation Area - Map of trails

    Indian Lands Conservation Area

    (11 reviews)

    This hidden gem has 2-3 miles of wooded trails for trailing running, dog walking, and light hiking…read more While the paved rail trail and the small beaches along the way are fun to explore, it's the wooded trails that are a win for me when I want a shaded run that's easy on the knees. Trails are well maintained and easy to navigate. Parking is available from the Main St Rail Trail Lot. For the wooded trail, you can either access it from the smaller secondary lot or take the main Rail Trail about a quarter mile down towards the river until you start seeing small paths on your left. There is a dirt service road with power lines running parallel to the rail trail that you will cross over. These power lines will also help navigate you back if you get turned around. I had to knock of a star because the trails are not marked so you can get turned around. Luckily the loops are short so you can't get too lost but don't be surprised if you end up in someone's driveway or come across a dirt road you weren't expecting. There are a few spots along the loops that have benches if you want to take a break and enjoy the views.

    Great place to walk the dog. Beautiful views of the river and marshes along the way. However,…read moretrails are not well-marked so you're never sure exactly where you are (as a newbie). Clear trail markers would be very helpful. Though there were several dogs off-leash, most were controlled by their owners. Definitely worth a visit!

    Tupancy Links - hiking - Updated May 2026

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