The 26-mile (42 km) system was built from the early 1890s through the 1930s, and initially owned by a state-level parks commission, which passed control to the city of Louisville in 1942.

Although Cowan proposed a slow and deliberate development, Mayor Charles Donald Jacob purchased what became Iroquois Park a year later and quickly began acquiring through donations the land to build 150-foot (46 m)-wide "Grand Boulevard" (later renamed Southern Parkway) connecting that southern property to the city.

Today there are various proposals being debated to ease traffic issues and restore connectivity of the city's parks via these routes.

The last of the parkways to be finished,[5] Algonquin was partially completed in 1928 by the Carey-Reed Company of Lexington at an initial cost of $120,000 with a width of just 20 feet (6.1 m) at the time, although space was reserved for widening once the area became more developed.

East of the university, there is an interchange with Interstate 65, and past that the parkway takes on a more residential feel for the rest of the route, with houses and apartment buildings on either side, except for near major intersections.

The final stretch of the parkway, past Bardstown Road, is the only two-lane portion outside of the U of L campus, although it is very wide, to allow for on-street parking.

Eastern Parkway ends in a roundabout at the entrance to Cherokee Park, at the center of which is a 1906 statue of Daniel Boone made by Enid Yandell.

A long portion of the route was donated by John Breckinridge Castleman, accounting for the sharp jog at the Baxter Avenue intersection.

Narrowing proposals were last made in 2006, although the plan was rejected since the traffic volume at the time, 21,000 vehicles per day, was too much for three lanes.

A large amount of the right-of-way was donated by Democratic Party boss John Henry Whallen, who made his residence near what is now Chickasaw Park.