Menemsha Hills – Martha’s Vineyard

Menemsha Hills Hike – Martha’s Vineyard

While the main population centers and tourist attractions are concentrated on the east side of the island, we would argue that the western half of Martha’s Vineyard, and more specifically Chilmark, is home to some of the most beautiful scenery on the island. Menemsha Hills, a 211-acre site managed by The Trustees, is easily one of the best places to experience the stunning coastline. If you’re willing to venture beyond Edgartown and Oak Bluffs and break a sweat, this hike is definitely worth a couple hours of your time.

Hike Summary

Distance: 3.0 miles is the shortest round-trip hike to beach. Option for 3.7-mile loop.

Difficulty: Easy

Map: Official Map; All Trails

Getting There

The trailhead and parking area is located on Trustees Lane off of North Road in Chilmark. It is about a 25-30 minute drive from Oak Bluffs or Edgartown and ~20 minutes from Vineyard Haven.

The Hike

The trail system consists of two loop trails (Harris and Nashawahkamuk) as well as the Beach Trail and the Brickyard Trail. For our hike, we chose to stay to the left the entire way, taking the most direct route to the beach and back (~3 miles round trip with a brief stop at Prospect Hill). There are multiple signs and maps posted along the trail. After a half mile, we stayed left on a small spur trail to take in the view from Prospect Hill. At 308 feet above sea level, it’s definitely not a towering peak, but it is only 3 feet shy of being the highest point on Martha’s Vineyard. There is a decent view of the ocean from Prospect Hill, but the views get much better as the hike progresses.

The trail eventually emerges from the trees, offering some amazing views of Vineyard Sound. The trail then descends back into a wooded area before reaching a scenic overlook with a stone bench.

At this point, the trail beings to descend down to the beach via a set of not-so-stable wooden stairs built into the hill. This section is fairly steep on the way back up, but it’s relatively short and not too strenuous.

The rocky beach is definitely no one’s first choice for sunbathing or building sandcastles, but it’s arguably one of the prettiest spots on the island, with views across the sound and dramatic cliffs on both sides. Outside of Maine, this is easily one of the most scenic stretches of coastline in all of New England.