The Pike Street portion of this building once served as the toll house for a suspension bridge that spanned the Delaware River here. The bridge opened in 1872 but was destroyed by an ice gorge several years later. There were several other bridges at this location after that and the current bridge was built in 1939. Portions of the Flo-Jean's property were once known as Kirk's Grove, a recreational and picnic area and a popular spot for band concerts and orchestras. The restaurant itself is well known and has had many noted patrons, including former New York State Governor Thomas E. Dewey.
Port Jervis used a street car system until 1924, one of only a handful of communities in Orange County to have one. While it never achieved great popularity, up and coming cities of the period boasted of having systems like it. By 1895, some 850 lines were in business around the country, operating on some 10,000 miles of track.
The line traveled along the city's most heavily used streets and connected the far-flung areas. While never particularly successful financially, the system was typical of urban lines. It was doomed however to a fate that was similar to the railroad's, as people came to depend on automobiles and trucks to travel and to ship materials.