The street was constructed in 1912 atop a covered trench of the New York, Westchester and Boston Railway that was cut through a hill.

Atop the hill, Esplanade intersects with Pelham Parkway, a road with its own series of green traffic medians designated as parkland.

The green spaces on the Esplanade have received designations by the city in honor of local residents who served the country in military service.

The triangle bound by the Esplanade, Pelham Parkway and Laconia Avenue is designated in 1993 as the Rudy Macina Peace Memorial Plaza.

[4] The median strip of the Esplanade at the corner of Astor Avenue[4] was designated in 1962 in memory of Private Sidney Weissman, a local resident killed in the sinking of the HMT Rohna.