This happened about 75 years ago. The top photo shows Powell Motor Company on Caroline Street in the early 1900s.
St. Thomas episcopal Church is at the far left and Halley's Service is at right but cannot be seen in this picture. I remember W. Powell's auto agency, but it was a Plymouth-Dodge franchise when I first recalled it. Mr. Powell lived in a large house on Piedmont Street which had a wide back yard and I occasionally cut the latter for 10 cents with my non-motorized push mower.
I also remember covering an Orange Town Council meeting in the 1940s and there was a big flap between Mr. Powell and the Orange Council which was attempting to widen Caroline Street at that time. H.C. Lonergan was the presiding mayor and there were sharp words exchanged between Powell and several council members-so much so that I was embarrassed. I cannot remember when or why Powell gave up the auto business, it was probably age, but I next recall that Page Higginbotham purchased the agency in the 1950s. d Tate ran the dealership and Janice Crockett was his secretary.
After several years, Mr. Higginbotham closed the business and Plymouth-Dodge went to Sprouse Motor Company on Madison Road which is now Terrapin Sports Supply. The Caroline Street building stayed empty for a number of years until the Orange County Bicentennial Commission in 1976 received a huge donation from Jack Taylor and purchased the property. Local architect Angus McDonald redesigned the front and the building became home of the James Madison Museum. The lower photo shows the structure as it looks today.