Most of us learn as children or as newcomers that our community is very old – 315 years old to be exact – yet not everywhere. Some areas of this little four-square-mile city are still being developed. Habitat For Humanity, for example, is building new houses on South Street on a rocky parcel that had always been vacant. Those four new houses, west of West Street, are in an area that was considered for building in other eras. Sometimes the dense limestone hills of west Newburgh were discouraging for builders; sometimes, the people who lived in many west-end houses opposed street expansion and scores of new homes added to their neighborhood. So, despite South Street being Route 52 with easy access to a trolley system, many of Newburgh’s west end hills stayed as nature created them for our city’s first two centuries.

There are maps filed in the Orange County land records office that outline early twentieth century development plans. Hillside Court, off Dupont Avenue, for example, would have been just the beginning of an extensive expansion of streets. Orchard Street, off West Street, would have been widened and paved and would have led to many additional streets planned during Newburgh’s boom years during and after World War I. That potential 1920’s -1930’s neighborhood would have been served by its own trolley (later bus) stop and shelter where Dupont Avenue splits from Broadway.

One of the expansion plans Newburgh did adopt in the late 1920’s was to add streets when Newburgh Free Academy moved uptown from Montgomery Street to Fullerton Avenue. Fullerton Avenue had only been open and paved from Broadway to South Street and a little beyond along Comfort’s Dairy Farm (the site purchased and demolished for NFA). In 1927, when everyone walked to school, and when the north end of Newburgh was being rapidly built up, it was plain to city officials that Fullerton Avenue needed to extend all the way out to North Street.
The same expansion was needed for the northern gateway to the city.

Traffic, including intercity buses, and all the farm trucks coming into the regional produce market from the busy orchards and vineyards of Middlehope and Marlboro, entered Newburgh along Balmville Road and proceeded down Liberty Street to Broadway and beyond. Until 1930, Route 9W included Mill Street and Balmville Road since it incorporated those routes to get into and through the city. In 1930, Route 9W was, therefore, approved by New York State for extension from the north end of Robinson Avenue to bypass the twisting corners at the Balmville Tree and to join the existing road to Middlehope that extended north from old Balmville School and on to Marlboro and Highland. Newburgh had opened a new northern gate.