Chilmark, Massachusetts (MA) Real Estate and Vacation Rentals on Martha's Vineyard

Real Estate Agent with Sandpiper Realty, Inc.

Chilmark on Martha's Vineyard, Massachusetts

<!-- End ImageReady Slices -->Beautiful homes set on rolling land. Rambling stone walls. Grazing sheep. One of the most beautiful of all Vineyard drives: Middle Road.

These are the trademarks of Chilmark – along with Chilmark Chocolates, made and sold in a small building just down from Beetlebung Corner. It is not unusual to encounter lines of customers spilling out into the parking lot, while those inside press their noses against the glass counters to make selections of their personal favorites (milk or dark? Nuts, or fruit?).

But Chilmark is about the sea as well as the land, even land as compelling as this.

At Menemsha, the last remnants of a fabled fishing fleet are tied up at the dock behind two fish markets where you can find the catch of the day. Here you can catch a bike ferry across to Lobsterville, take a catamaran trip to Cuttyhunk Island about an hour away, or climb out on the jetty to watch a spectacular sunset. Families bring folding chairs, and wine and cheese, and sit on the shore to do the same. The two fish markets pack up boiled lobsters for you to take down to the beach, complete with melted butter. An ice cream from The Galley, a tiny walk-up restaurant, completes the meal, if not the day.

Chilmark's small, rural community is located toward the western end of Martha's Vineyard. Most of its 10,639 (34 square miles) are devoted to residential and agricultural use – you can get fresh flowers at a Beetlebung Corner self-serve stand, Island-raised lamb at the Allen Farm and wool items knit from their own sheep, eggs from really free range chickens and bacon from local pigs.

The center of town houses a small elementary schoolhouse, originally a one-room school built circa 1850 and still in use for the 55 pre-kindergarten through Grade 5 students. There is also a tiny post office and a public library with a collection of videos and DVDs that would rival a small video store and a Vineyard room with a wonderful collection of everything Vineyard. In winter, the comfortable, bright seating areas in the library are favorite gathering spot for some of Chilmark's 650 people residents. Interesting adult and children's programs are scheduled year-round. The village also has a town hall built circa 1897, and a handsome church built in 1843.

Lest all that history weigh you down, the citizens of Chilmark have supported the Chilmark Community Center since 1956. It is the social epicenter of Chilmark. In July and August the Center hosts a program for children and families which offers a play school, a morning program with a full range of indoor and outdoor activities, and an evening program of movies, lectures, dancing and music for children and adults of all ages. Off-season, it provides the setting for a variety of events, including pre-school classes, wedding receptions, clambakes and the Fire Department's annual Christmas party. It's the site for cultural and social events through much of the year; choir and social performers particularly like its cozy welcoming atmosphere.

The Chilmark Store, just down the road and past Beetlebung Corner (named for the tupelo trees that dot the Island) is its own epicenter. Open only during the season, its porch is a hotspot that unites summer people who've not seen each other since the year before – many of them celebrities who fly in from Los Angeles or New York for relaxation. The porch, with its selection of rocking chairs and benches, is a great place to eat the breakfast foods, pizza and sandwiches prepared in the store – just bring a pencil and paper, in case you see someone from whom you might work up your nerve to collect an autograph.

If collecting autographs isn't your style (and most Vineyarders would disdain doing this), you might be able to rub elbows with the rich and famous (or the poor and fit) at the annual Chilmark Road Race. Now in its 31st year, the race takes place the second Saturday of August each year and attracts hundreds willing to make the beautiful 5K run along Middle Road. The celebrity watching may quickly get old while you struggle along the oh-so-hilly course, but the views of sprawling farmland, bucolic ponds and glimpses of the sea never do.


  • Menemsha Public Beach, next to the colorful Menemsha harbor. Safe for kids, with a lifeguard on duty and a roped off area.
  • Chilmark Pond Preserve. Small, dramatic and isolated, with parking for a few vehicles.
  • Great Rock Bight Preserve off North Road. The trail to the beach is long and steep and has stairs – but is worth it.

Also located in Chilmark is The Yard, a performing artists' colony tucked between hills and meadows in Chilmark. When The Yard was founded in 1973 by dancer and choreographer, Patricia N. Nanon, her vision was to create a space for contemporary dance artists to develop new works. The setting, three houses and a barn, now converted to a studio and a theater, surrounded by grass, woods and stone walls, is inspiring to both dancers and those who love to watch. The Yard has become a major cultural force on the Vineyard, bringing in diverse acts to the tiny theatre as well as widening their presence through performances around the Island.

Food, culture and social life just wouldn't be the same in Chilmark without the beaches. Many of them are private, including the much-admired Lucy Vincent Beach, but one that is not is accessible through Land Bank property at Chilmark Pond Preserve. If you bring your own kayak or canoe, you can park and paddle across the pond to an isolated Atlantic beach. Another, more accessible, swimming beach is at Menemsha, adjacent to the harbor.

The Menemsha Hills Reservation of the Trustees of Reservations also gives access, through a half-hour hike, to a spectacular overlook and rock-strewn beach – not for swimming -- on Vineyard Sound.

Martha's Vineyard Regional Transit buses link up-Island Chilmark and Aquinnah with the down-Island towns.

Comments (0)