This trail is part of the Conejo Recreation & Park District, managed by the Conejo Open Space Foundation. It’s a moderate 6.5-mile loop that gains and loses about 1000 feet of elevation—enough to feel like a real workout without being brutal. The route combines Mesa Trail and Box Canyon Trail, then follows a short stretch along Rocky High Road before dropping onto Lower Santa Rosa Trail. From there you’ll connect to Shooting Star Trail and climb up to Upper Santa Rosa Trail, which loops back to Mesa Trail and the parking lot.

The views across Santa Rosa Valley are genuinely worth the climb. You get the kind of wide-open vistas that remind you why Ventura County is worth exploring, especially when you hit the higher sections mid-loop. The trail itself is well-maintained, with a good mix of oak woodland and open hillside. On a clear day you can see across the valley in a way that makes the elevation gain feel justified.

Your dog needs to stay on a leash no longer than six feet the entire way. The trail is popular enough that you’ll probably see other hikers and dogs, so keeping a tight leash makes sense for everyone’s safety. Bring water for both of you—there’s no reliable water source along the route, and those sunny sections can get exposed depending on the season. The parking area is at the west end of Avenida de Los Arboles, right at the intersection with Big Sky. It’s a decent-sized lot that rarely fills up except on weekends, so you should be fine showing up most mornings. Clean up after your dog before you leave; the foundation keeps these trails in good shape partly because people actually respect that rule.