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.