The first portion of MD 155 near Havre de Grace was built by 1910; the remainder of the highway east of Hopewell Village was completed in the mid-1920s.

After the I-95 interchange, MD 155 passes north of the historic home Sion Hill and comes to an eastbound truck check station that heralds the steep descent from the bluff above the Susquehanna River to the city of Havre de Grace.

Close to the bottom of the hill, the state highway passes under CSX's Philadelphia Subdivision railroad line and turns south onto Ohio Street.

[1][3] MD 155 from Webster east follows the path of the old Bel Air Road from Havre de Grace.

As a result, the highway was paved from the city limits of Havre de Grace west to Lapidum Road by 1910.

[6] MD 155 was originally assigned to Aldino Road east from Churchville, then its modern path to Havre de Grace.

The state highway heads east as a two-lane undivided road between businesses and drops to one lane eastbound before reaching its eastern terminus at MD 155.