Hillside, overlooking Shinbone Alley, was built by mariner and shipwright Phineas Wright between 1714 and 1717. He willed the house two-thirds to his daughter Elizabeth and one-third to his sister Lydia provided she raised Elizabeth until she turned 21. Elizabeth survived and later married pilot William Adams. Lydia enlarged the property in 1729 with a land grant to the east of the house for a garden. She never married and lived in the house with her niece until her death in 1749.

In her will, Lydia freed her bondswoman Sue and gave her ‘the use of’ an enslaved boy named Kit ‘for her life’ and left the new property to her great-niece Mary Adams, the daughter of Elizabeth and William Adams. Mary was probably the ‘Miss Adams, daughter of the pilot’ listed in assessment records. She died in 1770, and the new property passed to her father who already owned the main house. He by then ran an upscale tavern offering ‘excellent liquors’ to ‘such gentlemen as will do him the honour’ to lodge with him. After his death in 1789 his widow, probably a second wife also called Elizabeth, and daughter probably by the second wife were left only two rooms in the house while the rest of the house presumably went to his children by his first wife.

In the 19th century, ownership passed to Elizabeth Roberts, the greatgranddaughter of Phineas Wright, and when she died in 1866 it went equally to her two daughters, Elizabeth Outerbridge and widowed Susan McCallan. Outerbridge promptly bought out her sister’s share, but the house returned to the McCallan family upon Elizabeth’s death when she bequeathed it to her nephew Samuel. In 1895 the property passed to Ernest A McCallan who also owned Seven Gables. In 1979 McCallan’s son sold the house to Steven Masters who initiated a major renovation. Hillside is a good example of an early grant house, boasting a Flemish gable, massive old chimneys and windows set high under the eaves. The side steps in front and an eastward wing on the southern end of the house were apparently added between 1867 and 1876 when William and Elizabeth Outerbridge lived there.