MD 299 heads northbound as two-lane undivided Massey Road and immediately has a grade crossing of the Chestertown Branch of the Northern Line of the Maryland and Delaware Railroad just west of the junction of the Centreville and Chestertown branches of the Northern Line.

The highway crosses Jacobs Creek before an intersection with the northern terminus of MD 290 (Galena Sassafras Road).

MD 299 reaches its northern terminus at US 301 (Blue Star Memorial Highway).

Sassafras Road continues northeast toward an intersection with MD 282 in the village of Warwick.

[1][2] MD 299 was paved as a concrete road from Massey to Sassafras in two sections in 1929 and 1930.