In the late 1980s, Maryland turned the southern portion of the B&A railroad into a rail trail and by 1986, the success from that led Anne Arundel County to declare intentions to do the same for the South Shore line, which they hoped to have open by 2000.

[1][2] As Part of state highway project, a bike lane along route 50 and the Severn River Bridge, connected the trail to Annapolis.

[2] On November 9, 1990 county leaders broke ground on a half-mile section of the trail between Waterbury Road and I-97 in Millersville, but work did not commence.

Then money became an issue when, in 1992 limited by a cap on tax revenue, the County Council voted to pull $270,000 from the trail project to repair the Lake Waterford dam in Pasadena.

At the same time, the project managers had to petition the Army Corps of Engineers for permission to use a portion of the rail bed that passed through what had since become wetlands.

[6][7] In 2001 the trail, this time the planned section along General's Highway, was facing public opposition because it would run through some people's front yards.

In 2000, the County had to buy a historic, two-story house on 2.9 acres along Cecil Avenue in Millersville to become the trail's headquarters because it was the only way to get a piece of property it needed.

That year, in construction related to the Nordstrom Wing of the Westfield Annapolis Mall, the County built 750 feet of trail between the Anne Arundel Medical Center and Jennifer Road.

[19] However, it wasn't until 2015 that the state provided the $990,000 needed to design and construct the first phase between Hansel Drive and Waterbury Road.

Built atop the railroad bed, that section extends more than 1.5 miles (2.4 km) to a point just east of Crain Highway.