MD 290 was reconstructed in Queen Anne's County and from south of Galena to Sassafras in the mid- to late 1950s.

The south leg of the intersection is county-maintained Benton Corners Road, which leads to Dudley's Chapel.

MD 290 heads north as two-lane undivided Dudley Corner Road, which crosses Red Lion Branch just south of its tight partial cloverleaf interchange with US 301 (Blue Star Memorial Highway).

The highway passes through the hamlet of Pondtown south of its intersection with MD 544 (McGinnes Road).

The highway turns east and runs concurrently with MD 291 (River Road) briefly before turning north toward Chesterville, where the route meets the south end of MD 444 (Locust Grove Road) next to the historic Chesterville Brick House.

East of the latter creek, MD 290 meets US 301 (Blue Star Memorial Highway) at a diamond interchange with ramps staggered into four intersections.

This work was funded by a $900,000 bond issue of Kent County used to build 50 miles (80 km) of 9-to-16-foot (2.7 to 4.9 m) concrete roads in those years.

The first step, reconstruction of the existing highway as a gravel road, was split into two sections both started in 1947.

[14] Work on the western segment included relocating the highway from what is now Olivet Hill Road.

[14] The highway from MD 300 to the new Crumpton bridge was reconstructed, widened, and surfaced with bituminous concrete in 1956 and 1957.