Montgomery Street laid out in the late 18th Century provided early access to Federal Hill from the surrounding neighborhood and ship yards at the base of the hill. Consisting of several blocks running west to east south of the Inner Harbor, Montgomery Street developed as a mainly residential street with its earliest major residence being built by John Eager Howard at in 1787. Over the course of the next one hundred years Montgomery Street provided sites for rows of Federal two and half story houses and three story Greek Revival and Italinate residences. These varied rows provided housing opportunities for the growing work force that found jobs in the expanding maritime and manufacturing enterprises.

By the 1950’s, however, much of the 19th Century manufacturing and maritime base that had provided employment for the Federal Hill neighbor had disappeared leaving vacant and decaying industrial sites with no alternative uses as well as a declining residential population. Looking at a neighborhood in distress with no apparent options for revival, the City government began planning for the Federal Highway over the top of Federal Hill with the Montgomery Street serving as the base of an elevated highway that would bring the road alignment from street level to the top of Federal Hill, across the Inner Harbor, then known as “The Basin” and down to Fell’s Point the north side of the “Basin”.

Through the actions taken by Society, not only was Federal Hill saved from the proposed Federal Highway, but Montgomery Street would no longer serve as the alignment for the bridge structure to the top of the Hill. With this success in preserving Montgomery Street the Society provided the framework for opportunities to renovate and restore the late 18th, 19th and 20th Century structures that line the street. Among the numerous historic structures that are now restored are the 1865 Ebenezer A.M.E. Church at 20 West Montgomery Street, the 18th Century house at 36 East Montgomery Street and the 1854 Watchman Fire House in the 200 block of East Montgomery Street.  

As a further protection from future Federal highway planning over Montgomery Street or through the neighborhood the Society was successful in having the Federal Hill neighborhood placed on the National Register of Historic Places. With this designation restoration and rehabilitation projects are eligible for Federal tax credits provided the projects meet the requirements of the Secretary of the Interior’s Standards for such projects. As a final protection and safeguard of the historic structures of the neighborhoods, the city designated the neighborhood as a city historic district which the Society long endorsed and work to have enacted.