This lollipop trail is one of three trails within Rockwoods Range. The other two include Fox Run and the hiking only Green Rock Trail. Roundhouse and Fox Run are multi-use trails. Expect to encounter equestrians on this trail.
This short loop is strenuous and fast when it's semi-smooth and dry, however, it's a quagmire for a long time after it rains. Additionally, the fall-line design and use by equestrians when the tread is muddy has taken their toll on the trail quality.
Starting at the Roundhouse parking lot located inside Greensfelder park and off of Allenton Road, head down a wide gravel road for about a quarter mile. Go past the hiking only Green Rock Trail and then veer right onto the doubletrack dirt Roundhouse Loop. The trail stays on top of the ridgeline climbing and descending the numerous saddles. Stay left at the intersection of the Fox Run Trail
Continuing another mile or so stay left at the top of a short climb. Heading right will drop you down a fall-line spur trail that ends at Fox Creek Road and the Green Rock parking lot.
Now the fun begins... when the trail is dry and hoof prints are minimal. The trail becomes rockier and quickly drops over 200+ vertical feet to the valley floor. Be sure to avoid the large rain ruts and large, loose rocks. Now begin a gentle grade as the wide trail follows a creek drainage.
Before you know what hit you, following the sweeping left-hander you are forced to climb a steep grade. The long hill is broken up into 4 steep pitches with very short semi-level to downhill grades to let you catch your breath. By the time you get to the last climb you may wonder how there could be a hill this long in Missouri. The last 200 feet goes straight up and is very loose and rocky. Topping out at the gravel road, turn right and ride around the Roundhouse Memorial. Descend the gravel and head back the way you came until you get to the Roundhouse parking lot. Whew!