Overlooking the town of Los Gatos and the south bay, Sierra Azul Open Space Preserve is the District’s largest preserve, encompassing over 18,000 acres of mostly rugged and steep terrain. If you’re bringing your dog, know upfront that leashed dogs are allowed only on the trails in the Kennedy-Limekiln Area, accessible from Kennedy Road in Los Gatos and from Highway 17, adjacent to Lexington Reservoir County Park and St. Joseph’s Hill Open Space Preserve. This restriction makes sense given the preserve’s size and rugged character — the rest of the property is steep, exposed, and best left to experienced hikers without dogs.

The Kennedy-Limekiln loop itself covers over 14 miles and includes nearly 2,000 feet in elevation gain, so it’s genuinely challenging. You’ll want to start early, bring plenty of water for both of you, and be realistic about your fitness level. The trail system here serves hikers, bicyclists, and equestrians, so you’ll encounter other users on the path. The views across the south bay make the effort worthwhile, and the elevation gain means you’re climbing into quieter territory as the day goes on.

This isn’t a casual neighborhood walk — it’s a serious hiking destination where you need to bring the right gear and physical conditioning. Sections can get rocky underfoot, and the exposure on some ridges means you want a dog who’s comfortable with heights and responsive to commands. The preserve does ask visitors to Leave Only Paw Prints, which means packing out everything you bring in, including water bottles and waste bags.

If you’re considering this loop, check conditions before you go since weather can make the steep sections significantly more difficult. The adjacent Lexington Reservoir and St. Joseph’s Hill properties offer additional options if you want something less demanding on the same day.