When the glaciers passed through millennia ago, they left a striking calling card that later became the westernmost end of the Island: the colorful Gay Head cliffs, one of the most recognizable landmarks on the East Coast and Aquinnah’s geological claim to fame. To the southwest is Nomans Land, now a wildlife preserve; to the right are the Elizabeth Islands. The restaurants and shops at the cliffs are favorites of Islanders and visitors alike. The lighthouse is built of red bricks made from the clay of the cliffs, and is open for sunset tours on summer weekends. Formerly known as Gay Head, Aquinnah is home to the Wampanoag Tribe of Gay Head, descendants of the Island’s original inhabitants.
Rolling hills, dusty private lanes, ambling sheep, sweeping ocean views, ancient stone walls, and unspoiled beaches are reminiscent, to some, of Ireland. While more distant from the down-Island attractions, Chilmark residents like it that way and rely instead on their own busy community center, library, and general store.
Technically, Menemsha is part of Chilmark, but it’s uniquely its own place. For years this quaint fishing village was home to a sizeable swordfishing fleet. Today, though pleasure craft outnumber the fishing boats, it is still an active commercial harbor and a great place to soak up some local color. Walk along the dock and get a close-up view of draggers and lobster boats or climb out onto the jetty and fish. It’s an ideal destination for fresh seafood to-go and a blazing sunset.
Just a short drive from Vineyard Haven and a world apart, West Tisbury is the agrarian heart of the Island. Its agricultural hall, general store, town hall, and church form the gathering places for the town’s relatively small year-round population which blossoms in the summer. Home to a State Forest, miles of farmland, open space, and the Island’s 150-year-old annual Agricultural Fair, West Tisbury is a quintessential rural New England village.
Points of Interest
Gay Head Cliffs - The cliffs are a half-mile long along a path from the Aquinnah town parking lot.
Gay Head Light - It was built in 1799 to warn ships of the shoals known as Devil’s Bridge where, in 1884, the City of Columbus ran aground and 122 people drowned.
Menemsha Village - In 1905, Menemsha creek was dredged to form the working fishing basin it is today. Near Dutcher Dock (named for Vineyard journalist Rodney Dutcher) are fish markets, inns, eateries, and more, and it is one of the most popular spots to watch the sunset.
Beetlebung Corner - Located in Chilmark is the site of a beetlebung (tupelo tree) grove. The unusually dense wood was used for beetles (mallets) and bungs (plugs for barrels). The word “beetlebung” was coined on the Vineyard.
West Tisbury Town Center - Includes the First Congregational Church, town hall, Alley’s General Store, the library, Grange Hall, Howes House, and the Field Gallery.
Grange Hall - Built in 1859, it is run by the Martha’s Vineyard Preservation Trust and serves as home to the seasonal Farmers Market, artisans fairs, antique shows, and other community gatherings.
Old Mill Pond - The area at the junction of Edgartown-West Tisbury Road and State Road was a gristmill in 1760. Today it is sometimes called Swan Pond, named after its seasonal occupants.
The Youth Hostel - On Edgartown-Vineyard Haven Road in West Tisbury, it was built in 3 weeks in the 1950s, and accommodates budget-minded travelers.
Agricultural Hall - On Panhandle Road, the Ag Hall is the sight for the annual Fair in late August, as well as many other community events, from weddings to art shows.
Polly Hill Arboretum - Created by the late Polly Hill in 1958, it encompasses 20 acres of walking trails and 40 acres of woodland.
Christiantown Chapel - Off Indian Hill Road, the original 1659 structure commemorates the site of Thomas Mayhew’s first missionary movement of convert native Islanders to Christianity. A sacred graveyard is nearby.
Vineyard Haven (Tisbury)
As the major entry port to the Island, Vineyard Haven is the most vital town on a year-round basis. Established by the English in 1674, its harbor is home to the Steamship Authority’s main terminal as well as shipyards, marinas, traditional boat builders, and several full-size replicas of majestic tall ships. The historic downtown features charming boutiques, restaurants, a major hotel, fitness center, theaters, and a thriving art gallery community.
Points of interest
West Chop Lighthouse - Two miles from downtown Vineyard Haven on Main Street, the wooden lighthouse originally built on the northernmost headland in 1817 was the last manned lighthouse on the Island.
Owen Park - On upper Main Street, this park is the result of Mr. William Barry Owen’s insistence on a clear view of the harbor from his William Street mansion. It has benches, swings, a gazebo bandstand, and a public beach next to the town wharf pier.
The Stone Church - Christ United Methodist Church, located at the corner of Church and William streets, was built in 1923. The church basement houses the off-season Island Food Pantry that serves more than 1,200 Vineyard residents each year.
The Vineyard Playhouse - Built in 1833 on a pasture donated by Captain William Daggett, the building at 24 Church Street began as the first Methodist meetinghouse. It became the Capawock Hall market in 1855, and was owned by the Masons until 1982, when it was converted to the Island’s year-round, nonprofit theater company.
Katharine Cornell Memorial Theatre - Above Tisbury Town Hall at 51 Spring Street is the Katharine Cornell Theatre, housed in a building that was a place of worship in 1844. In 1971, with funding by famed actress and seasonal resident Katharine Cornell, the second floor was transformed into a meeting room/theater. It features murals of Island history and legends by the late Island artist Stan Murphy.
Captain Richard C. Luce House - This private residence at 40 William Street was the first Greek revival house in Vineyard Haven and built in 1833 for whaling captain Richard Luce.
War Memorial Veterans Park - Located off Lagoon Pond Road near Five Corners, the 10-acre plus playing field was created by the Vineyard American Legion in memory of World War II veterans, and in 1964, donated to the town of Tisbury.
Oak Bluffs and Edgartown
If you’re looking for a sedate New England village, skip now to another town. Oak Bluffs is colorful, brash, fun, and proud of it. Brimming with life all summer long, from one end of Circuit Avenue to the other, this former Methodist campground-turned-resort’s gingerbread architecture, shops, restaurants, movie theaters, pubs, ice cream stores, calm surf, and teenage hang-outs epitomize seasonal beach living at its best. The town plays host to traditional family activities including fireworks, band concerts, and sing-a-longs, along with its magical Illumination Night.
Points of Interest
East Chop Lighthouse - Originally built in 1802 on Telegraph Hill, the lighthouse is on the site of the signal station that received semaphore messages from Woods Hole to indicate the arrival of homebound whaling ships. The current lighthouse was built in 1877.
Flying Horses Carousel - Owned by the M.V. Preservation Trust and listed in the National Register of Historic Places, the oldest continuously operated carousel in the country is at the foot of Circuit Avenue on Oak Bluffs Avenue. The hand-crafted carousel has been a feature on the Vineyard since 1884.
Memorial Statue - In a rare tribute, the 1891 fountain monument at the edge of Ocean Park was dedicated to Union soldiers by Confederate soldier Charles T. Strahan of the First Virginia Regiment, who settled on the Island and became the editor of the Martha’s Vineyard Herald. In 1925 a plaque was added to commemorate Confederate soldiers.
Ocean Park - Across from the Steamship Authority pier and partially surrounded by Victorian gingerbread cottages, the recently restored park is the site of the annual Oak Bluffs fireworks and summer band concerts.
Union Chapel - Built in 1870, this octagonal, non-denominational chapel off Circuit Avenue at the juncture of Kennebec and Narragansett avenues, was intended for use by non-Campground residents who did not attend the Methodist church with its prohibition on alcohol.
The Campground - Tucked behind Circuit Avenue, this Methodist-founded campground began as a retreat in 1835. More than 300 brightly-decorated gingerbread cottages are settled around the wrought-iron Tabernacle, currently the site of events and the high school graduation.
Originally known as Great Harbour when it became the first English settlement on the Vineyard in 1642, Edgartown really came into its own in the 19th century at the height of the whaling industry. As whaling captains returned home, they built the stately mansions that still grace the streets. With its brick sidewalks, up-scale boutiques & galleries, and world-class yachts, Edgartown is the Island’s oldest of towns, complete with rose-covered white picket fences, elegant inns, and fine dining. But just a couple of miles outside the Village, South Beach’s crashing waves entice body surfers to one of the Island’s largest public beaches. Also, just a short ferry ride across the harbor is the island of Chappaquiddick.
Points of Interest
Memorial Park - Often called Cannonball Park, it is located between Upper Main Street, Edgartown-West Tisbury Road, and Cooke Street. It was dedicated on July 4, 1901 to the 70 Vineyard soldiers who died in the Civil War.
Martha’s Vineyard Museum - At 59 School Street, the museum includes the Thomas Cooke House with period furnishings; the Pease House with five galleries of art and architecture; the Carriage House with its 1854 fire wagon; the 1856 Ross Fresnel lens from the Gay Head lighthouse; and an archival library.
Daniel Fisher House - This Greek Revival-Federalist structure at 99 Main Street was built in 1840 by doctor and businessman Dr. Fisher. Founder and first president of M.V. National Bank, he was considered to be the wealthiest man on the Vineyard in the mid-1800s.
Vincent House - Behind the Daniel Fisher House is the oldest Vineyard house, built in 1672 on Edgartown Great Pond by William Vincent and eventually moved to its present location off Church Street. Each of its restored rooms represents a different century on the Vineyard.
Old Whaling Church - Owned and operated by the M.V. Preservation Trust, this meeting and performing arts center on Main Street was built as a Methodist church. An example of Greek Revival architecture, it was designed by Frederick Baylies Jr. in 1843.
Visitors Center - At 29 Church Street, the visitors center provides information, restrooms, a post office annex, and from Memorial Day through Labor Day, refreshments. It is the central site for bus transfers.
County Courthouse - In addition to its regular judicial business, the two-story red brick courthouse at 51 Main Street is where the Superior Court convenes. It was constructed in 1858 with bricks made at the old Chilmark brickyard.
Federated Church - At 45 South Summer Street, the oldest church on the Vineyard – Baptist until 1925, now Congregationalist – was designed by Frederick Baylies Jr. in 1828.
Captain Pease House - The residence was built at 80 South Water Street in 1836 by Valentine Pease, captain of the Acushnet, and who scholars believe was the model for novelist Herman Melville’s Captain Ahab of “Moby Dick.” Melville went whaling with Captain Pease in 1841.
Old Sculpin Gallery - Across from the Chappy ferry in a building more than 250 years old is the Old Sculpin Gallery, home of the M.V. Art Association, incorporated in 1954. The gallery, with its wide-planked floor, hand-hewn beams, and permanent collection display, is open from mid-June to mid-October when it hosts art classes and shows.
Memorial Wharf - Adjacent of the Chappy ferry, the two-story structure offers picnic tables and views of Edgartown harbor.
Chappy Ferry - Dock street is where the ferry On Time makes its two-minute run across the channel.
Edgartown Lighthouse - Originally built in 1828, then replaced in 1938, this oft-photographed lighthouse, maintained by the M.V. Museum, is a popular location for wedding ceremonies.