The Town of Castle Rock recently connected the various sections of this trail into a ten mile loop. There are sign posts at most intersections so it's easy to ride the whole trail as one big loop or bypass sections for a shorter ride. There's nothing too technical, but some tight, loose turns, a few switchbacks, and a couple of short climbs make for an excellent after work ride right in the middle of town.
Park at the Coachline Road trailhead and ride the big loop clockwise. Just ride through the signposts in reverse alphabetical order (O - A). Be prepared for an awesome roller coaster of a ride, but do be careful and keep your speed in check as you'll likely encounter many other trail users (and some blind corners).