The trail runs along the former path of the Sacramento Northern Railway which provided freight and passenger rail service between Oakland and Chico between 1912 and 1957.
Plans at one point called for the creation of CA Highway 77 that would have followed the railroad's right of way right through the Oakland Hills. Local opposition to the planned highway caused the project to be cancelled and spurred the creation of the Shepherd Canyon Corridor Plan. The fruits of this plan include Shepherd Canyon Park and the Montclair Railroad Trail.
The path is paved through most of its length. The first mile of trail also has fairly good tree cover. Though homes and businesses are never too far away, there are pockets of solitude and relative quiet.
Rail lines are laid out to avoid rises in elevation that are too steep for locomotives to handle. For walkers and cyclists this means rail to trail paths feature a pleasant easy grade even in cases where the line leads uphill. That's certainly the case here as well.
The first mile of trail is by far the most pleasant stretch of the trail. Once it reaches Bishop Court it becomes little more than a sidewalk along the busy Shepherd Canyon Road. If you're not intent on walking its entire length, that's a good place to turn around and double back.