It represents the single best preserved area of mid 19th century houses in Vineyard Haven.

[2] One of the earliest English settlements on the island of Martha's Vineyard (now in Massachusetts) was a place called Holmes Hole.

[2] The street was developed by Thomas Bradley, who also counted a mill in West Tisbury among his businesses.

These houses were all built by local builders, apparently without the benefit of architectural guidance.

[3] The historic district encompasses all of the properties from Woodlawn Avenue in the north to Camp Street, extending about three houses south of the latter.