In addition to trails within various parks in the system, Kirkwood is also a connecting point for the eight-mile Grant’s Trail that follows the old Carondolet branch of the Missouri Pacific Railroad. The Kirkwood Trailhead is located at the corner of Leffingwell and Holmes and follows street connectors to Kirkwood Park.
Greentree Park is a connecting point for the Meramec River Greenway trail. This trail stretches from Greentree Park to just past Highway 141 in Valley Park.