The junction of Jamaica Avenue and the Van Wyck Expressway marks an interesting element in Queens County history.
During the Revolutionary War, Jamaica and what later would be called Richmond Hill chose overwhelmingly to remain loyal to the British crown. That stance later brought the wrath of New York’s lawmakers down upon the residents.
A tollbooth was established at the spot, becoming a money maker much like the modern tolls of today. The location was the entry to the thriving village of Jamaica along what historically had been called the Brooklyn and Jamaica Plank Road. It also marked the final eastbound stop on the trolley line that ran all the way down to Williamsburg, Brooklyn, and was later replaced with a bus route.
With the announcement of the consolidation of the five boroughs to form the greater City of New York in 1898, the toll booth was shut down and demolished.
After World War II, a commercial truck route running north and south was needed in the area. Work on the Van Wyck Expressway, named for the first five-borough mayor, who served until 1901, began in 1946 and wrapped up in 1950. Since trucks cannot use the Cross Island or Grand Central parkways, the new highway gave area streets much-needed relief.
Imagine the money that could be made if the toll booth were brought back today — though the gridlock would bring everything to a standstill.