The highway was extended southeast through Mayo to Beverley Beach in the late 1920s and early 1930s.

The route heads north as a two-lane undivided road that forms the main street through the Londontowne area of Edgewater.

[4] The highway was extended as a gravel road to near the present MD 214 intersection by 1921 and to the entrance to Camp Letts by 1923.

[8][9] The state highway reached MD 214's present terminus in Beverley Beach in 1932.

[10][11] By 1934, traffic on MD 253 was dense enough that the Maryland State Roads Commission recommended widening the highway from 16 to 20 feet (4.9 to 6.1 m) from Edgewater to Beverley Beach.