I was sent the second and fourth photos by Jane Lunden, whose grandfather, T. Fred Dowling, formerly owned this diner. The barrel roofed model was replaced by a double ended Sterling Streamliner, possibly a secondhand diner from Connecticut. It stayed in the family through the 1960s, at which point it was sold. After that, it’s unclear what became of the diner, other than that the site is now home to car repair businesses.
The first photo is from the NYPL collections, and shows the barrel roof model in a different color scheme.
If anyone has any further information on this diner, its history, or when it was demolished, please contact me.
Diner Hunter 
Dowling’s Flyer was Sterling Diner # 4107 and was built in 1941. It measured 14′ wide and 54′ long and was sold with a factory kitchen addition. The Streamliner model was shipped from the J.B. Judkins factory in Merrimac Massachusetts on July 8 1941. The cost of labor and materials for the diner was $15,199.41. The sale price of Sterling Streamliner Diner #4107 was $22,145.
Only know it was a neighborhood institution, and my first introduction to a slice of pickle with a hamburger. Fond memories of Dowling’s diner from late 50’s early 60’s. It was the streamliner then, exterior was a light green color.
The diner was sold to a Greek family who operated the diner for awhile. Rose Dowling was not well enough to continue to run the diner and her children did not want it.
Laura Dowling Loughran
Granddaughter of Fred Dowling