Chilmark

Islanders escape the summer crowds for the quiet fishing villages along Chilmark’s coastline, the most infamous of which, is Menemsha. It’s not unusual to see families waiting in line at The Bite, the Back Door at Homeport or Larsen’s Fish Market to get their “to-go” container of fresh-caught seafood to eat on the beach during spectucular sunsets.  The kids catch blue crabs in the saltwater pond and listen to guitar players that often show up to play a tune for nature’s event. 

Chilmark has often been mistaken for Ireland on many a Sunday drive. After all, how often do you see rambling sheep grazing alongside ancient cobblestone walls with sweeping views of the ocean? The arts are well-supported in this community’s summer Film Festival with Cinema Circus being a favorite of children after a long day of hiking Prospect Hill (the highest point on the island), or swimming at one of its picturesque resident beaches.

Chilmark boasts some of the priciest private real estate on the island, however, many owners have offered up the rental experience of their beautiful Cape Cod style homes and modern, luxury beach retreats with both inland water view and waterfront locations.

Where to Stay:

Central/Middle Road:  lush farmland with acreage and executive homes.
Menemsha:  fishing village harbor busy with small shops, restaurants and beaches.
North Shore:  rural, scenic and private with oak forests and babbling brooks and ocean vistas.
South Shore: windswept seagrass, stonewall roads and some of the island’s finest private beaches.

Beaches:

Lucy Vincent Beach
Menemsha Public Beach
Squibnocket Beach