Bootleggers Run is a singletrack footpath that is winds throughout the upper portion of Creve Coeur Park from Dorsett Road. The trail was constructed by GORC and their many helpful volunteers.
The Bootleggers Run Trailhead is located just past the tennis court in a gravel parking in the upper portion of the park. There are no running water or restroom facilities at the trailhead but facilities do exist nearby.
When you think of Bootleggers Run what thoughts come to mind? Most likely, you conjure up a dark, quiet, winding back road, one that is fairly remote. The image in you imagination could just as easily be Bootleggers Run. Although you are never far from park activities or from civilization, this trail feels remote.
Just within the woodline, and shortly after the start, the trail splits. Heading to the left will ultimately take you back to the trailhead parking lot. Taking the right branch leads to a dead end loop, which you'll then follow back. This description leads to the right.
Early in the route, the trail crosses the old trolley line. As the trolley is long out of use, this looks much like an old roadbed. Cinders can still be seen packed on the surface of the right away, restricting tree growth. At this intersection, continue to the left. Here the valley will open up below. During construction, the trolley line had to pass up over the valley as much as 80 feet to make the line nearly level. The original trolley line brought visitors from Creve Coeur Park to both Delmar and Kingston. The trolley line was constructed in 1899 and many visitors were able to enjoy the lake because of it.
The final trail section is 1 mile in length. In summer months, the trail is nicely shaded. This trail meanders through one of the prettiest woodlands in the park. Many different tree types such as majestic tall oaks, hickories, basswood and other tree species overshadow the trail.
One of the biggest trees in the park is found in this final stretch. This tree has seen much history, and probably was present with the City of St. Louis was founded by the French in 1764. Today it is massive; the first branch coming off of the trunk is bigger than most trees. Though the age of the tree makes discerning the species difficult, it appears to be a red oak and has a circumference of 16 feet 2 inches.