John and Mary Smith Cottage // c.1800

One of the most charming cottages in Edgartown is this half-cape on South Summer Street, which retains its unique character amidst the extreme wealth and desire for expansion of summer homes on Martha’s Vineyard. This home dates to around the turn of the 19th century (possibly older) and in the 1800s, was home to John Sprague Smith (1808-1893) and his wife, Mary Norton Smith. John S. Smith, like most of the community, was a mariner and lived in the house until his death in 1893. The house was not originally on this lot, however, as it was originally built on the south side of S. Water Street and moved to its present location by later owner, Allen P. Stewart, a fisherman, woodcarver and artist who made wooden ducks. The house has since been added onto at the rear, but the diminutive and charming facade has been retained, with its early 20th century shed dormer on the front slope of the roof. 

Captain Thomas N. Fisher House // c.1856

One of the more intricate Sea Captain’s residences on Martha’s Vineyard, can be found here on South Summer Street in Edgartown, a unique Gothic Revival residence notable for its carved bargeboards and full-length porch. The residence appears to have been built around 1856 for Thomas N. Fisher (1819-1885), a whaling captain who married his wife Phebe, leaving her soon after in this home on a whaling voyage. Historians state that Captain Fisher was a strict disciplinarian and one of a very few whaling masters to forbid prostitutes on board his ship. He served many more excursions even through the Civil War when whaling vessels were particularly prone to attacks by Confederate raiders. It is said that Captain Fisher cut the top of his topmasts to disguise his ship as an English rig to sail safely home. In 1885, Captain Fisher died of a heart attack while at church in Edgartown, but his residence remains well-preserved much like it was when maintained by his wife while he was away for months or years at a time out at sea.  

Holmes W. Smith House // c.1835

The architecturally distinguished Holmes Smith House on South Summer Street in Edgartown, Martha’s Vineyard, showcases the range in which the Greek Revival style could showcase whimsy and unique architectural details from the typical side-hall gable-end form seen all over New England. The house appears to date from the mid 1830s with its strong, symmetrical facade of flushboard siding, its three bays divided with paneled pilasters, and elaborate parapet containing a central dormer and arched fan motifs. The house was originally owned by Capt. Holmes Wass Smith (1798-1849) and his wife, Sophia (Coffin) Smith and later in the 19th and early 20th centuries by members of the Pease family. The residence is now a summer home and has been thoughtfully preserved as one of the most excellent and unique examples of its style on Martha’s Vineyard. 

Collins-Schofield House // c.1750

One of the older Colonial-era homes in Martha’s Vineyard, is this 2 1/2-story, side-gable, half-house clad in wood shingles on South Water Street in Edgartown. Deed research has not been undertaken, but a 1858 map shows the property owned by the estate of Palfrey Collins (1777-1857), who worked as a ship rigger, mariner, and day laborer on a nearby wharf, primarily on vessels preparing for whaling voyages from Edgartown. In the late 19th and early 20th centuries, the property was owned by sea captain, Ira V. Schofield (1837-1918). The residence retains its Colonial charm, including the (possibly original) eight-over-twelve and twelve-over-twelve sash windows, and door surround with transom over the paneled door.

Nunnepog House // c.1840

Located on South Water Street in Edgartown, Massachusetts, the Nunnepog House stands as one of the finest mid-19th century homes on Martha’s Vineyard. The residence was built by Joseph Allen Athearn (1807-1867), who is listed in the Census as a carpenter. The first known owner is Edmund Bradley (1786-1869), then a retired sea captain, who lived here until his death. In the 1930s, the house became well known as The Seagull and the Whale, a shop in which Louise Meikleham sold homemade jams, jellies, and breads and later became her residence, known as the Nunnepog House, derived from the original Wampanoag name for the area encompassing Edgartown and Oak Bluffs on Martha’s Vineyard. The residence was moved to its present site in the 1950s or 60s and was more recently renovated and expanded from plans by Patrick Ahearn Architects. The residence is unusual for its four-bay facade with offset entrance and features many hallmarks of the Greek Revival style, including cornice returns, paneled corner pilasters, a wide frieze, and classical entry. The half-fan windows and corresponding shutters are a great design element of the facade which makes it stand out from other period homes.


Captain Thomas Milton House // 1840

Located on the idyllic South Water Street in Edgartown, Martha’s Vineyard, the Capt. Thomas Milton House stands as a fine and well-preserved example of a sea captain’s house built in the Greek Revival style. Captain Thomas Milton (1787-1862) was born in Liverpool, England, and first arrived to the island as a young man aboard a whaling vessel. He served as a Lieutenant and privateer during the War of 1812, when England restricted trade to maritime ports, which severely crippled the Edgartown economy. After the embargo ended, Captain Milton led whaling vessels and trade routes to as far as China. On his last trade excursion to China in 1837, Captain Thomas Milton brought back a sapling of a Pagoda Tree that was planted on the lot of his soon-to-be-built house on Water Street. Construction began on the house in 1840, which is unique for its asymmetrical four-bay facade and low hipped roof. Captain Milton died in 1862 and by the turn of the century, his residence was converted to an inn, which is now a part of the multi-building, Harborside Inn complex. The property has stood here for nearly 200 years joined by the ever-growing Pagoda Tree, which is believed to be the largest of its kind in North America. 

Union Chapel // 1870

One of the most unique buildings I have ever seen is the Union Chapel in Oak Bluffs on Martha’s Vineyard. The chapel, built in 1870 in the American Stick Style, is in the form of an Octagon, very unique for churches. Built as an inter-denominational house of worship, it is significant as the first non-sectarian religious building to be erected in a community that until 1870, was noted primarily for its strong association with the Methodist Church and its summer camp meeting (Wesleyan Grove) assemblies. The Chapel offered islanders and seasonal visitors regardless of religious affiliation not only an opportunity to worship but a gathering place for cultural activities. According to historic images, the chapel once had more elaborate stick work and finials, since removed, likely due to storms and general maintenance concerns. The chapel was designed by island resident Samuel Freeman Pratt (1824-1920) who had no known architectural training besides working as a wood carver in Boston, yet his work is characterized as having a dynamic and festive style. Pratt’s other major contribution to Oak Bluffs’ architecture, the Sea View Hotel, was erected at the head of the wharf in 1872, but burned down in 1892.

“Seas the Day” Cottage // 1875

This quaint little summer cottage in Wesleyan Grove was built in 1875 for Hanson Arnold, a merchant and methodist from Woonsocket, R.I. The home is typical of many other summer cottages in Oak Bluffs on Martha’s Vineyard, with its delicate stick work, turned posts, full-length porch, and second story balcony with pierced bargeboards. The home was at one point named “Seas the Day”, a trend of naming the cottages occurred sometime in the 20th century by families who summered on the island, many incorporating the family’s name somehow. The home was restored recently with all new detailing and a reversion back to the original porch configuration.

Riday-Evans Cottage // c.1880

This cottage on Ocean Ave in Oak Bluffs was built before 1880 for J.F. Riday, a manager at the American Mail and Export Journal at the Wesleyan Building on Bromfield Street in Boston. The quaint cottage was photographed shortly after it was built with Riday and two women (one likely being his wife) posing on the front porch overlooking the ocean. By the early 20th century, the home was owned by George and Corielle Evans, a couple from Mexico. They likely modified the home with the shingled siding and front porch with sheltered balcony above, while the original lancet windows and doors remained.