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Skyline Blvd – Big Bear Trailhead loop from Orinda Oaks Park

Skyline Blvd – Big Bear Trailhead loop from Orinda Oaks Park

Moderate

4.7

(2713)

10,008

riders

Skyline Blvd – Big Bear Trailhead loop from Orinda Oaks Park

02:24

39.1km

590m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: June 27, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 13.7 km for 3.08 km

After 19.1 km for 82 m

Waypoints

Start point

Bus stop

Get Directions

5.11 km

Valle Verde Trailhead Lafayette

Highlight • Trail

Valle Vista is the trailhead for the paved Lafayette-Moraga Regional Trail, a popular rail-trail for cyclists. There’s a restroom here, but note: the EBMUD dirt trails are hiking-only and require …

Tip by

8.47 km

Upper San Leandro Reservoir overlook

Highlight • Viewpoint

Pinehurst Road leads along the upper reservoir from the crest all the way to the junction with Canyon Rd. There are only a few open viewpoints to see the Upper …

Tip by

13.7 km

Grass Valley Trail (Anthony Chabot Regional Park)

Highlight (Segment) • Trail

Grass Valley trail follows the lush meadows along Grass Valley Creek from its origin at Parkridge in Anthony Chabot Regional Park south to the intersection with Brandon Trail. This recorded …

Tip by

19.1 km

Equestrian Center

Highlight • Rest Area

Stables and starting point for horseback riding into Anthony Chabot and Redwood Regional Park.

Tip by

19.2 km

Anthony Chabot Equestrian Center Riding Stables

Highlight • Rest Area

Anthony Chabot Equestrian Center is a working-class ranch that sports four-plus barns housing about ninety hoofed critters. Riders can walk, flat walk, trot, gait, canter, lope, or gallop their fleet-footed …

Tip by

22.4 km

Skyline Blvd

Highlight (Segment) • Cycleway

Beautiful section of Skyline, a wide 4-lane boulevard separated by a tree-lined center median parkway, winding along the crest above Leona in the Oakland hills.

Tip by

27.0 km

Big Bear Trailhead

Highlight • Trail

Big Bear trailhead is the parking spot to link to Golden Spike Trail on the north side of the road, the Macdonald Trail and Big Bear Trail on the south …

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27.9 km

Redwood Regional Park South Entrance

Highlight • Rest Area

As Redwood Road follows Redwood Creek upstream, it skirts the South and West side of Redwood Regional Park, or go straight into Redwood Park Entrance Road, which becomes a gravel Multi-Use Trail after a mile, closed to cars, but bikable.

Tip by

39.1 km

End point

Bus stop

Way Types & Surfaces

Way Types

22.2 km

12.7 km

3.10 km

940 m

138 m

Surfaces

31.2 km

4.58 km

3.19 km

170 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (360 m)

Lowest point (140 m)

Weather

Sunday 19 July

27°C

12°C

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Comments

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Skyline Blvd – Big Bear Trailhead loop from Orinda Oaks Park

Valle Verde Trailhead Lafayette

Upper San Leandro Reservoir overlook

Grass Valley Trail (Anthony Chabot Regional Park)

Equestrian Center

Anthony Chabot Equestrian Center Riding Stables

Skyline Blvd

Big Bear Trailhead

Redwood Regional Park South Entrance

Nearby routes

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