History
Several rolling roads were established in Maryland in the early 18th century for the transportation of tobacco in casks, or hogsheads, from plantations to river ports. These casks were pulled along the road by slaves and later oxen before this method of freight transportation was made obsolete by the introduction of sturdy wagons. The rolling road in western Baltimore County connecting Rockdale with Elkridge, which was likely built in 1714 by William Summers, is the only such road in Maryland whose name survived to modern times. South Rolling Road was improved as a macadam road from Washington Boulevard (later US 1) to Frederick Road (later US 40 and now MD 144) by 1921. In St. Denis, the highway that was to become MD 166 followed modern Arlington Avenue and East Street south across a grade crossing of the B&O Railroad to its southern terminus at Washington Boulevard. MD 166 was moved to modern South Rolling Road when the highway's bridge over the railroad was built in 1931. By 1933, North Rolling Road was upgraded to an improved county highway. North Rolling Road would be expanded to a divided highway in Woodlawn around 1981. Unlike South Rolling Road, North Rolling Road has never been a part of the state highway system.
The next major changes to MD 166 came in the early 1970s with the construction of I-95 and Metropolitan Boulevard, the latter of which went under construction in 1969. When I-95 was completed through Arbutus in 1971, South Rolling Road was split. Metropolitan Boulevard opened from the US 1 ramps northwest through the I-95 interchange to an intersection with Sulphur Spring Road just south of the modern Selford Road overpass in August 1974. South Rolling Road was truncated in St. Denis by the construction of the US 1 ramps. The freeway was extended to its present terminus at Rolling Road and the ramps to UMBC Boulevard were constructed in 1975. Metropolitan Boulevard south of the I-95 interchange was marked as a second segment of MD 46—disjoint from the section between MD 295 and Baltimore/Washington International Airport—from when it opened. North of I-95, the freeway was marked as a relocation of MD 166. MD 166 was extended to US 1 and replaced that segment of MD 46 by 1981. MD 166 was truncated to its present southern terminus when I-195 was completed in June 1990.
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