The Montclair Railroad Trail in Oakland winds through the Montclair Hills and connects directly to Redwood Park, making it one of the more accessible routes in the East Bay if you’re coming from the hills neighborhoods. The trail follows the historic railroad bed, so you get that satisfying sense of walking an established path with some history to it. The terrain is gentle with gradual slopes, which makes it manageable for dogs of different fitness levels and ages.

You’ll see a mix of oak woodland and open areas as you move along the trail. It’s popular with the whole neighborhood—joggers, cyclists, families heading to school, casual walkers. The trail feels well-used and well-maintained, and because it connects to Redwood Park, you can easily extend a short walk into a longer outing if your dog’s got the energy for it.

Dogs must stay leashed the entire time, which matters if your dog needs some off-leash time to really burn energy. That said, the trail itself is appealing enough that most dogs seem content with a good on-leash walk, especially since there’s enough scenery and elevation change to keep things interesting. The route works particularly well as a morning walk—the Montclair Hills neighborhoods feed into the trail, so it doesn’t require a car trip to access if you live in that part of Oakland.

The official Oakland wiki page for the trail has details on different access points, which is useful if you’re trying to figure out where to start depending on where you’re coming from. Parking is available at various spots near the trailheads, though during school hours some of the nearby streets get busier with parent drop-off traffic.