MD 291 parallels the Chester River along the southern edge of Kent County and connects Chestertown with U.S. Route 301 (US 301).

The highway was extended west toward Chesterville in the early 1930s, but it was not complete to MD 290 until the late 1940s.

MD 291 crosses Morgan Creek on a steel truss bridge on its way to Morgnec, where the highway's name changes to River Road at its intersection with Morgnec Road, which heads north and then east further from the Chester River than MD 291.

MD 291 crosses Mills Branch as it approaches its indirect interchange with US 301 (Blue Star Memorial Highway).

MD 291 continues east into the town of Millington, through which the highway passes as Cypress Street.

In the center of town, the highway intersects MD 313 (Sassafras Street) and the Centreville Branch of the Northern Line of the Maryland and Delaware Railroad at-grade.

[4][5] The concrete highway was extended west from Millington to Mills Branch in two sections, the eastern part completed in 1933 and the western segment built in 1934 and 1935.

[6][7][8] Kent County included the portion of River Road between MD 290 and Mills Branch as its top priority in the post-war construction program; that segment was surfaced and brought into the state highway system as an extension of MD 291 in 1946.

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.

[12][19] Work shifted to the original stretch of MD 291 in the late 1960s, when the highway was resurfaced with bituminous concrete from US 301 to the east side of Millington in 1967.