Maryland Route 396 is the route designation of the extension of Massachusetts Avenue from Washington, D.C., into Bethesda, Maryland. The Maryland section of Massachusetts Avenue runs for just over 2 miles (3.2 km) from Westmoreland Circle at the District line to Goldsboro Road (Maryland Route 614).

Beginning at MD 614 (Goldsboro Road), MD 396 proceeds southeast as Massachusetts Avenue, a two-lane road with shoulders, fronted by homes and sidewalks. At Sangamore Road, the road widens to four lanes of a divided roadway, still in a residential area. The Capital Crescent Trail passes over MD 396 via an overpass north of the Little Falls Parkway. The state highway terminates at Westmoreland Circle, at the District boundary. Westmoreland Circle provides access to Western Avenue and Massachusetts Avenue south into the District, as well as local roads on each side of the border.

The entire route is in Bethesda, Montgomery County.

MD 396A is the designation for the 0.10-mile (0.16 km) portion of Westmoreland Circle on the Maryland side of the District of Columbia boundary. The three-lane, one-way highway begins on the east side of the circle at Western Avenue. MD 396A continues counterclockwise around the circle through intersections with MD 396 and Wetherill Road before ending on the west side of the circle at Dalecarlia Parkway.