Captain Fisher House // 1892

Standing out amongst the Federal and Greek Revival homes in Edgartown, this Victorian home was constructed in 1892 by Captain Charles W. Fisher (1835-1905) for his new wife. The Fisher family includes many members who were active in the local whaling industry. Fisher is said to have caught the largest sperm whale on record in 1884 and apparently loved being on the open ocean. The next year he married Parnell Pease and she sailed with him to the Pacific on a whaling voyage, lasting five years! At the time of their marriage, Fisher was in his 50s and his new wife in her 20s. Upon their return, Fisher built his wife this “modern style house on the pretentious side with Victorian ornamentation.” Unfortunately, his wife preferred her former house, which was a block a way and obscured any views of the water. Tradition states that apparently, Mrs. Fisher had seen enough of the water during her voyage, as her diary on the five year trip detailed her many unfortunate bouts with sea-sickness, a stay on an island, and dangerous storms.

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.

Jones Cottage // 1876

This charming little cottage in Oak Bluffs was built in 1876 for Charles N. Jones, a resident of Medford, MA who had a home built there in 1872. His family’s summer cottage on Martha’s Vineyard was designed by the Ripley Brothers, Alonzo and Walter, carpenters who lived in town and designed and built many of the charming little summer homes there. The home features a wrap-around porch, a covered balcony at the second floor, and pierced board balustrade and cornerboards. Oh, and the paint scheme is perfect!

Aunt Georgia’s House // c.1880

Located on the iconic Circuit Street in Oak Bluffs, this Eclectic Victorian cottage has a storied past related to Black history on the island. Even though Oak Bluffs was a relatively safe place for African Americans to be, there were still limits on their rights. In some parts of Oak Bluffs there were laws that said that certain property could only be owned by whites. The island became a vacation spot for thousands every summer in the 19th century and seeing a lack of options for Black travelers, Mrs. Georgia O’Brien and Ms. Louisa Izett began to operate an inn for people of color. The inn was one of two such residences in Oak Bluffs and has since been listed on the African American Heritage Trail of Martha’s Vineyard. The home has since been named the Tivoli Inn and retains much of the original gingerbread trim. In recent years, Martha’s Vineyard was given the nickname, “The Black Hamptons,” due to its popularity as a place for wealthy African-Americans to vacation, it remains a very diverse island in summer months.