Explore the most popular trails near Chilmark with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Chilmark, Massachusetts Map
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hiking
rocky
washed out
4 months ago

Really nice trail - you can walk along the beach to connect to two staircases. The beach is great but not for swimming.

Great trail and large rock beach

walking
Sat Nov 03 2018

Very nice trail. Woods opening up to some beautiful ocean vistas.

Great trail system, though trail maps could be updated. Has open meadows, mature Woodlands, hilltop views, and creek access. Great place to walk leashed dogs. Meadows are occasionally grazed by a herd of goats.

Mon Sep 10 2018

Provides access to public and town beach. Surrounded by coastal shrubland that's great fo Monarch Butterflies and birds like common yellowthroats.

Mon Sep 10 2018

Great loop for dog walking.

Really pretty after a light snow.

Both loops are nice. Brautiful views from the bluffs over the shore and from Prospect Hill.

Wonderful hike/walk. I did the whole loop and I will say, I’m pretty rusty at hiking right now and I considered this to be easy, not moderate.

Nice little walk. Nothing too strenuous and not much up and down, but a good little walk. It's definitely an easy "hike" not moderate. The rock is interesting and there was an area along the trail with goats. Very cute!

walking
Sun Jul 16 2017

Headed down to the beach for a day of sun. The trail was well marked, out and back. There is a location near the bottom (South end) where you can unload and load chairs and beach toys, and then drive up and park, and hike the trail down to the beach. Decent little trail. The draw to this trail is the view and scenery, without question.

Pretty easy hike. A new path down to the beach has been added. It came in handy because the original path was closed for security because the Obamas were vacationing nearby!

Great overlooks.

Nice easy hike with varied terrain. Beautiful views of the Sound, Elizabeth Islands, and back towards Menemsha village.

mountain biking
30 days ago

hiking
2 months ago

mountain biking
3 months ago

mountain biking
4 months ago

hiking
5 months ago

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