Cheeseboro and Palo Comado Canyons are 4,000 acres in the northernmost section of the Santa Monica Mountains National Recreation Area, in the Simi Hills. Stroll to Sulphur Springs or hike to the top of Simi Peak for panoramic views of Oak Park, Agoura Hills and Simi Valley. The Chumash lived in these canyons for thousands of years. Many trails within the canyons may have originated with the Chumash and then were expanded by the ranchers who followed.
Cheeseboro Canyon has some of the best cycling and running trails in the area. The lower trailhead is accessed from Cheseboro Road and there is plenty of parking. (On a side note, no one has been able to explain to me why Cheseboro Road is spelled differently than Cheeseboro Canyon.)
Cheeseboro Canyon Trail (CCT) is a 4.6 mile, fairly easygoing main artery into the park, whereas the 4.4 mile Palo Comado Canyon Trail, which largely parallels the CCT, is much more challenging. The Cheeseboro Ridge Trail also parallels the CCT and seems to be favored by cyclists with its long, rolling hills, though distance runners also will enjoy this trail. Take CCT up through Sulphur Springs and you'll be running through a small (usually) stream bed and a brief rotten egg smell. Then soon the trail becomes more desert-like as you make your way up to the Sheep Corral Trail and the Shepherds' Flat area. It is really beautiful up there though it can get pretty hot, so carry some water!
While there are plenty of steep hills in this area, this is also a great place for strollers, as many of the trails are quite wide and flat.
The only bathroom that I'm aware of in these trails is at the Cheseboro Road trailhead and is not particularly pleasurable to use...just a heads up.
Visit www.nps.gov/samo/planyourvisit/cheeseboropalocomado.htm to learn more and to access a nice pdf trail map. The trailhead is located at 5792 Cheseboro Road. Contact the visitor center at 805.370.2301.