Marthas Vineyard Guide

Before the arrival of English colonists, Aquinnah was inhabited by the Wampanoag Tribe, the original Martha’s Vineyard natives.  Prior to 1998 Aquinnah was officially known as Gay Head, a name which many islanders still use today.  One of Martha’s Vineyard’s outermost locations, in 2000 the census revealed just 344 residents.  Perched high on a bluff, with the famed Gay Head Cliffs below, you can see most of Martha’s Vineyard on a clear day from Aquinnah. The cliffs are composed of 150 feet of sediment comprised of red and white clays, green sands, white quartz, black organic soil, and lignite. They tell the story of the past hundred million years, one colorful layer at a time. Beaches call visitors to come and sit and let go of the rest of the world. Tourists browse in the tiny shops at the look-out and buy souvenirs for family and friends. Locals enjoy breakfast in the simple restaurant on the cliffs with an incredible view. Aquinnah is remote, beautiful and peaceful.

Chilmark was first settled in 1660 by James Allen, William Peabody, and Lt. Josiah Standish (son of Captain Myles Standish) in the southern portion of Tisbury.  The first town to separate from the two original Martha’s Vineyard towns of Tisbury and Edgartown, Chilmark was incorporated in 1694.  Today Chilmark is a wonderfully exclusive and serene locale, where residents a from around the globe chat quietly behind Prada glasses, lithe dancers from The Yard are reputed to rehearse "au naturel," and incredible mansions and beach houses are hidden from sight down long dirt roads. In the quaint and bustling fishing village of Menemsha local fishermen bypass 100-ft private yachts as they enter a harbor that has changed little in the past 50 years. Sip wine on the beach (BYOB) and watch the fiery sunset nightly—and applaud when it dips below the horizon. Chilmark is about understated elegance, privacy, affluence and discretion. The town consists of a quaint country store, a post office, town hall, a fire station, a small selection of restaurants, and the Chilmark Community Center where locals go for films, talks, tennis and fitness classes. The farm-country beauty of Chilmark is loved by those who frequent this amazing part of Martha’s Vineyard.

Edgartown was first settled in 1642 by the English.  Led by Reverand Thomas Mayhew, Jr., settlers colonized on Martha’s Vineyard island after its purchase by his father Thomas Mayhew.  Edgartown was originally called Great Harbor, and was incorporated in 1671 as one of Martha’s Vineyard island’s two original towns.  Edgartown’s current name was given in honor of Edgar, the youngest son of James II of England, after he died at the age of four.  Edgartown’s history is fameous, having been well known as a primary port for the whaling industry in the 1800’s.  The booming industry gave rise to grand mansions built by successful captains, which still stand in gleaming white perfection today.  Edgartown is the high-end social center of Martha’s Vineyard, and is home to some of Martha’s Vineyard’s most fabulous restaurants, museums, and of course, Hob Knob.  Get an ice cream and stroll the picturesque streets, meet friends for a cocktail, sit and take in the bustling harbor activity, or hop the On Time ferry and explore famous Chappaquiddick.  There is no shortage of elegance and beauty in Edgartown.

Originally a part of Edgartown, Oak Bluffs, which was first settled in 1642, was incorporated in 1990 as Cottage City, and again in 1907 under its current name.  Oak Bluffs was the original center of tourism on Martha’s Vineyard, with its grand Victorian homes, The Flying Horses Carousel (the oldest carousel in America), and the Methodist Church’s settlement “The Campground.”  Today Oak Bluffs is the most diverse of Martha’s Vineyard towns, with colorful gingerbread cottages and Victorian homes that line the streets.  As one of the few island towns that serves alcohol, Oak Bluff’s shops, bars, restaurants, bustle with activity year-round. There’s always something going on in Oak Bluffs. Parasail or Jet Ski right from the docks. Listen to a free concert at Ocean Park or the Tabernacle. Experience Illumination Night in the Campground, where over 100 incredible Victorian beach cottages hang lanterns, creating magical display that will delight the senses. You’ll never be bored in Oak Bluffs.

Known by Martha’s Vineyard’s original Wampanoag inhabitants as Nobnocket, Vineyard Haven (also known as Tisbury) was first referred to by coloniel settlers as Homes Hole.  “Homes” from a Wampanoag germ for “old man,” and “Hole” meaning a sheltered inlet.  By the 1800s it was more commonly spelled Holmes, as a reference to John Holmes who settled the village during the second half of the eighteenth century.  Holmes Hole officially became Vineyard Haven in 1871.  Today Vineyard Haven is the largest of Martha’s Vineyard’s down-island towns, and the main port of entry for those traveling to Martha’s Vineyard by ferry. Vineyard Haven offers tremendous shopping along Main Street, stunning waterfront beach homes, quaint boat yards, the Black Dog café, and Owen Park with public access to the harbor. Vineyard Haven is a main hub of Martha’s Vineyard’s arts community, with the Vineyard Playhouse, the Katharine Cornell Theater and the Martha’s Vineyard Hebrew Center all calling it home. Vineyard Haven is your destination for activities that stimulate our mind, creativity and spirit.

West Tisbury was first settled by English settlers in 1669 as part of the town of Tisbury.  The town was the last on Martha’s Vineyard to incorporate, doing so in 1669.  Historically West Tisbury has been the agricultural center of Martha’s Vineyard.  It is the largest town by land area, and spans the center of Martha’s Vineyard island. West Tisbury is home to Alley’s General Store, the Field Gallery with its playful white statues, the Martha’s Vineyard airport, Lambert’s Cove beach, and the Martha’s Vineyard state forest. Predominantly a rural town, with farms, stables, and the local winery, West Tisbury has two small town centers with a grocery store, banks, a yoga studio, pharmacy, the general store, a gas station and a few shops. Art galleries sit off winding country roads, the twice weekly Farmers Market and Artisans Festivals are packed during summer months, and for a few wonderful days in August it is home to The Dukes County Fair. Many year-round residents live in this comfortable, rural community with rolling fields and an easy-going manner.