The highway crosses Jacobs Creek before an intersection with the northern terminus of MD 290 (Galena Sassafras Road). MD 299 continues northeast as Galena Sassafras Road, which passes the historic home Rich Hill and crosses Herring Branch into the village of Sassafras.
The highway crosses Jacobs Creek before reaching a junction with the northern end of MD 290 (Galena Sassafras Road). MD 299 continues northeast as Galena Sassafras Road, which passes Rich Hill and crosses Herring Branch into the village of Sassafras.