Bay Overlook – Skyline Boulevard loop from Lake Merritt

Bay Overlook – Skyline Boulevard loop from Lake Merritt

Hard

3.3

(4)

riders

Bay Overlook – Skyline Boulevard loop from Lake Merritt

02:52

53.9km

980m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: September 10, 2026

Tips

Includes a segment in which cycling is not permitted

After 53.1 km for 51 m

Waypoints

Start point

Train Station

Get Directions

13.9 km

Bay Overlook

Highlight • Viewpoint

A nice reward after climbing up Tunnel Road and Skyline Boulevard!

Tip by

15.4 km

Skyline Boulevard

Highlight (Segment) • Cycleway

With rolling climbs up and down, this area is wooded, paved, and often foggy. When the fog breaks, enjoy photo opportunities of the Bay Area.

Tip by

17.3 km

Skyline Gate Redwood Regional Park

Highlight • Rest Area

Skyline Boulevard crests near the entrance to Redwood Regional Park. There are bathrooms and viewpoints into the park that drops to the east, generally north-east along and below the ridge of the Oakland hills.

Tip by

26.8 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

33.8 km

Old San Leandro Creek Stone Bridge

Highlight • Bridge

Pinehurst Road descends into a grove of tall redwood trees just before reaching an old stone bridge. There is a tiny group of houses and a post office tucked beneath the towering forest giants.

Tip by

38.0 km

Huckleberry Botanic Regional Preserve Upper Pinehurst Entry

Highlight • Trail

A fully protected area (no biking inside) on the East side of the Oakland hills, sloping down between Sibley Volcanic Preserve and Redwood Regional Park.

Tip by

52.9 km