Kennedy Trail – Kennedy Road loop from Oak Meadow

Routes

Mountain biking trails

Kennedy Trail – Kennedy Road loop from Oak Meadow

Moderate

4.9

(6566)

15,703

riders

Kennedy Trail – Kennedy Road loop from Oak Meadow

02:23

24.2km

720m

Mountain biking

Moderate mountain bike ride. Good fitness required. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: August 9, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Sierra Azul Open Space Preserve

Waypoints

Start point

Train Station

Get Directions

62 m

Billy Jones Wildcat Railroad and W.E. "Bill" Mason Carousel

Highlight • Structure

Historic 19th century logging train preserved and now used for joyrides around Vasona Park, Los Gatos

Tip by

520 m

Los Gatos Creek Trail (Vasona Park Entrance)

Highlight • Trail

Blossom Hill Rd entrance to the Large Vasona Park that stretches around lakes formed in the Los Gatos Creek watershed. Good place to stop for picnic, restrooms, water fountains.

Tip by

12.1 km

Priest Rock Trail/Kennedy Trail Junction

Highlight • Trail

Ride a little (200m) past the intersection of Kennedy/PriestRock and you'll find a nice vantage point to your right: good for a rest and 360*-views.

Tip by

12.1 km

Kennedy Trail

Highlight (Segment) • Trail

When you reach the trailhead of "Kennedy Trail", a climb starts right away but ends very quickly and is even followed by a coast down a gentle downhill.

The "real" …

Tip by

18.4 km

Kennedy Road Sierra Azul Trailhead

Highlight • Trail

The Kennedy Road Sierra Azul Trailhead has a small parking area that fits about three cars, depending on size, and offers a shaded starting point. A portable toilet is available …

Tip by

18.5 km

Kennedy Road

Highlight (Segment) • Cycleway

From Top of the Hill Road and the Kennedy Trailhead the 2-lane Kennedy Road descends to both directions: to the East along Shannon Creek, and here to the west along …

Tip by

24.2 km

End point

Train Station

Way Types & Surfaces

Way Types