The Boot Trail starts at the intersection of six differnt trails and, unless you're looking to doubletrack it back, this will be your singletrack option for heading back to the Glasgow St. parking lot.
Boot is essentially divided into two trails, and it definitely feels like a different trail after crossing The Main Trail (Multi-Use). The first section is rated as a black diamond on the trail signage, which I can only imagine is due to the grunt factor. There is a decent climb to start this trail, but the many switchbacks keep you enticed. Once you cross The Main Trail (Multi-Use), you'll start a gradual descent towards Monkey Boy.