Oak Bluffs Town Hall & Fire Station // 1882

Located at the heart of Oak Bluffs, this modest, wood-frame building has held some of the most important civic and cultural uses on the island. Built in 1882, the growing town of Cottage City (later renamed Oak Bluffs), which separated from Edgartown, needed a new town hall and fire station with the rapid development caused by summer visitors and increased year-round residents. After WWII, the property was renovated and expanded to allow space for a small police department in the building as well. In 1966, a new town hall was built across from the ferry pier at the waterfront, and the town soon after sold the former, outdated building, and two years later, it was purchased by The Cottagers, Inc. The Cottagers, Inc., is a philanthropic organization founded in 1955 by a group of African-American women who owned cottages or homes on Martha’s Vineyard. The social group provided a safe space for the growing Black community who lived on and visited Martha’s Vineyard. The building remains as an iconic landmark not only for its historical use and architecture, but as a symbol of the diversity and the black community in the small island town.

South Congregational Church // 1824

Built in 1824, the South Church in Kennebunkport Village looked very much as it does today, with the exception of the portico, which was added in 1912. In the early 19th century, architects were seldom employed in such remote areas therefore, builders often used manuals and examples of other churches in addition to their own experience gained from working the large shipbuilding yards adjacent to the Kennebunk River. The cupola, restored in 1991, is designed after an example by Christopher Wren and the steeple retains the original 1824 Aaron Willard clock with its unique wooden face, still keeps accurate time and rings on the hour. The church remains as an active space with a growing congregation in the summer months.

Eastham Windmill // 1793

Built in 1793, the Eastham Windmill on the old Town Green is the oldest workable gristmill on Cape Cod. Typical of Cape Cod, Eastham’s windmill is an octagonal , “hat and smock” or Flemish design in which the revolving top or hat can be rotated to direct the sails into the wind. Local historians contend that Thomas Paine, a noted early millwright and resident of Eastham, most likely built the Eastham Windmill in the late eighteenth century. Some sources state that the windmill was likely built in Plymouth and later moved to Truro and eventually to Eastham in 1793. In 1895, the women of the Village Improvement Society raised money to purchase the windmill and two adjoining properties from private ownership for $ 113.50. Around the turn of the twentieth century, the windmill became a local tourist attraction and the subject of postcards and souvenirs. The windmill is now the main attraction of the annual Eastham Windmill Weekend.