Grant's Trail was once part of the Missouri pacificrailroad line. Freight trains would come from Kirkwood on their way to the Mississippi River via this route and cross by ferry for eastern connections. This section was known as the Carondelet or Kirkwood Branch and provided an alternative to crowded downtown rail lines. The ferry closed in 1940 and this portion of rail line was abandoned in 1990.

It was purchased by Trailnet in 1991 under the Rails to Trails Act. The trail is a 75 acre corridor 100 feet wide and 5.8 miles long running mostly parallel to Gravois Creek.

Construction of the trail began in 1994. By September 18th, when the trail officially opened, 800 feet had been paved, two additional miles were graveled, and the first bridge, Dillman Bridge, had been built. St. Louis County Executive "Buzz" Westfall commemorated this milestone with a ribbon cutting ceremony, and the trail was named the Carondelet Greenway.

In the early days of this trail most of the physical work was performed by volunteers including boy scouts, cyclists, Trailnet board members and staff, and AmeriCorps. In fact, the Dillman Bridge - the first bridge from the trailhead at Orlando's Gardens was named after Trailnet board member Bob Dillman who, with a small volunteer crew, actually built it.

The construction of the trail was truly an example of community involvement. AmeriCorps volunteers worked six weeks preparing the trail for major construction. They planted trees, worked on sewers and culverts, cleared brush and did much of the work at Grasso Springs Pond. Other volunteers did supplemental construction on the trails including fences and culverts. There were 21 Eagle Scout projects which added such things as safety signage, landscaping, bridges, erosion control, mile markers, mulch bins and rest areas.

It took nearly three more years before another four miles were paved. Pat Jones, widow of Ted Jones, the father of the Katy Trail, helped fund acquisition and requested that the name be changed to Grant's Trail. On July 6, the name and turned the trail over to St. Louis County Parks for operation and maintenance. Grant's Trail is still owned by Trailnet.

The Koepke St. Louis Bicycle Park is being developed by volunteers on land presently leased from Metropolitan Sewer District(MSD). Located off Mount Olive, this park includes a mountain bike section and a BMX Trail.