Explore the most popular hiking 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.

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!

Sunday, July 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.

Saturday, August 20, 2016

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!

Saturday, December 26, 2015

Great overlooks.

Tuesday, November 24, 2015

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

12 days ago

1 month ago

Saturday, September 12, 2015

Sunday, July 19, 2015

Friday, June 21, 2013