Kennedy Trail – Kennedy Road loop from Oak Meadow
Kennedy Trail – Kennedy Road loop from Oak Meadow
4.9
(6566)
15,703
riders
Kennedy Trail – Kennedy Road loop from Oak Meadow
02:23
24.3km
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: April 29, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
Waypoints
Start point
Train Station
Get Directions
62 m
Billy Jones Wildcat Railroad and W.E. "Bill" Mason Carousel
Highlight • Structure
Tip by
520 m
Los Gatos Creek Trail (Vasona Park Entrance)
Highlight • Trail
Tip by
12.2 km
Priest Rock Trail/Kennedy Trail Junction
Highlight • Trail
Tip by
12.2 km
Kennedy Trail
Highlight (Segment) • Trail
The "real" …
Tip by
18.5 km
Kennedy Road Sierra Azul Trailhead
Highlight • Trail
Tip by
18.5 km
Kennedy Road
Highlight (Segment) • Cycleway
Tip by
24.3 km
End point
Train Station
Way Types & Surfaces
Way Types
12.7 km
6.34 km
4.02 km
920 m
193 m
< 100 m
Surfaces
12.8 km
10.0 km
1.38 km
< 100 m
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Elevation
Highest point (780 m)
Lowest point (90 m)
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Weather
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Today
Tuesday 23 June
29°C
14°C
0 %
Additional weather tips
Max wind speed: 18.0 km/h
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Description
If you're looking for a challenging and rewarding mountain biking experience in the South Bay, the Kennedy Trail – Kennedy Road loop from Oak Meadow is definitely worth your time. This moderate 15.1-mile (24.3 km) route packs in 2368 feet (722 metres) of elevation gain, typically taking around 2 hours and 22 minutes to complete. It's a fantastic option for fit riders seeking a demanding climb with expansive views, especially if you enjoy a good workout on wide fire roads.
What to expect on Kennedy Trail – Kennedy Road loop from Oak Meadow
The journey on this loop is a true test of endurance, starting with an initial flat and downhill section before the "real" climb begins. As you ascend the Kennedy Trail, the terrain shifts from packed dirt to rocky and rutted sections, with grades often hitting 14-16% and some pitches exceeding 25%. The effort is well worth it, though, as the views open up to reveal the sprawling urban landscape of San Jose and the East Bay Hills, with the rugged Santa Cruz Mountains providing a dramatic backdrop to your right. You'll pass a "false summit" before tackling two more steep pitches, making this route best suited for confident mountain bikers who thrive on sustained climbs.
Planning your visit
The Kennedy Trail is a popular spot, especially for events like the annual Kennedy Turkey Day Ride, so expect company on the weekends. Oak Meadow Park serves as a convenient access point, and while parking is generally available, arriving earlier in the day is always a good idea. Be sure to carry plenty of water, especially during warmer months, as much of the trail is exposed, offering continuous views through the foliage rather than dense shade. The trail is open year-round, but spring and fall offer the most pleasant riding conditions.
Trail details
- Distance: 15.1 miles (24.3 km)
- Elevation gain: 2368 feet (722 metres)
- Difficulty: moderate
- Estimated time: 2 hours and 22 minutes
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