The best running trails around Cupertino

Prepare for a challenging jogging experience on the Stephen E. Abbors and Upper Wildcat Canyon Loop, a difficult 9.0 miles (14.5 km) route that climbs 1154 feet (352 metres) over an estimated 1 hour and 50 minutes. You'll start by ascending a grassy, oak-studded hillside, then transition into a pleasantly wooded canyon. As you gain elevation, you'll enjoy increasingly scenic views of the Santa Clara Valley, especially from the High Meadow Vista Point, before descending into cool, shady bay laurel woods.

When planning your visit, be aware that parking at the trailhead can be challenging on nice summer weekends, often requiring a wait. Some sections of the trail are exposed, so it can get very hot if you jog on days above 85 degrees Fahrenheit. Consider an early start to avoid the midday heat and potential parking delays.

This route offers a dynamic journey through varied landscapes, moving between sunny chaparral and dense, lush woods with fern groundcover. A unique feature of the canyon is the subtle perfumed scent that sometimes emanates from the dense bay tree woods, adding an unexpected sensory element to your jog.

Embark on the Tony Look to Coyote Ridge Loop for a moderate jogging experience that blends shaded single-track paths with open fire roads. As you move along the Tony Look Trail, you will find yourself enjoying views of the Stevens Creek Reservoir. The route covers 6.1 miles (9.9 km) and involves an elevation gain of 816 feet (249 metres), typically taking about 1 hour and 16 minutes to complete.

When planning your visit, be aware that this loop is a popular spot for various outdoor enthusiasts. You will share the path with hikers, equestrians, and cyclists, so stay alert and be considerate of others. Parking is generally available at the trailhead, making access straightforward for your jogging session.

This loop offers more than just a workout; it provides expansive panoramic views of San Jose and the surrounding valley, especially as you climb the Coyote Ridge Trail towards Maisie's Peak. The varied terrain, including unpaved dirt and gravel sections, means you should be sure-footed, but it also adds to the diverse character of your jogging adventure.

Embark on the High Meadow and Wildcat Loop for a moderate jogging experience covering 5.7 miles (9.2 km) with an elevation gain of 818 feet (249 metres). This route typically takes about 1 hour and 8 minutes to complete, offering a varied landscape as you move through the preserve. You will encounter a mix of wider fire roads and narrower single-track paths, with sections providing welcome tree coverage. Keep an eye out for the High Meadow Vista Point, which offers expansive 360-degree views of the surrounding Bay Area.

Planning your visit to the High Meadow and Wildcat Loop is key, especially if you prefer a quieter experience. This trail system is quite popular, particularly on weekends, so consider starting your jog early in the morning or choosing a weekday. This approach helps you avoid the busiest times and enjoy the natural surroundings more peacefully. The preserve's diverse network of trails also allows you to extend or modify your route if you wish to explore further.

A unique highlight along the High Meadow and Wildcat Loop is Deer Hollow Farm, a working farm that features animals and an organic garden. This adds an interesting, pastoral element to your jogging adventure, setting it apart from many other trails in the region. The combination of natural beauty, varied terrain, and this distinctive farm makes the route a well-rounded option for joggers seeking both exercise and engaging scenery.

Embark on the Parker Ranch Trail to Nob Hill Loop, a moderate jogging route spanning 4.3 miles (6.9 km). You will gain 706 feet (215 metres) in elevation, with most people completing the circuit in about 49 minutes. The trail offers a varied experience, mixing unpaved paths, gravel, and some paved sections, including challenging climbs and a steep stairway early on. From the Nob Hill viewpoint, you can enjoy panoramic views of the rolling hills and the bay, often enhanced by wildflowers in season.

This route is easily accessible, with multiple trailheads, including the main one located on Prospect Road. It is a multi-use path, so be prepared to share the way with hikers and equestrians. If you bring your dog, please keep them on a leash to ensure a pleasant experience for everyone on the trail.

Located within the Fremont Older Open Space Preserve, this loop provides a solid workout amidst natural beauty. The diverse terrain and rewarding vistas make it a popular choice for those looking to combine exercise with scenic views. It's a great way to explore the preserve and take in the expansive landscape of the region.