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Bay Overlook – Skyline Boulevard loop from MacArthur

Bay Overlook – Skyline Boulevard loop from MacArthur

Moderate

4.9

(6744)

11,090

riders

Bay Overlook – Skyline Boulevard loop from MacArthur

02:16

41.3km

790m

Road cycling

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

Last updated: August 13, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Sibley Volcanic Regional Preserve

Waypoints

Start point

Train Station

Get Directions

11.3 km

Bay Overlook

Highlight • Viewpoint

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

Tip by

12.8 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

14.1 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

22.8 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

30.6 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

32.2 km

Shepherd Canyon / Montclair Railroad Trail

Highlight (Segment) • Trail

Beautiful rail-to-trail route, that manages to climb gradually the rather steep Oakland hills above Montclair, half of this section is high above Shepherd Canyon road, until it merges closer, but …

Tip by

34.4 km

Snake Road bridge (Montclair/Shepherd Canyon)

Highlight • Bridge

Some brilliant engineering of this old gradual railroad grade, climbing across the canyon cut by Snake Road below.

Tip by

39.3 km

Linda & Rose Avenue Park

Highlight • Rest Area

Small neighborhood park along Linda Ave, which is a quiet residential street ok for biking, e.g. to climb through Piedmont toward the Oakland Hills to Redwood Regional Park and other mountain bike trails komoot.de/tour/14468615

Tip by

41.3 km

End point

Train Station

Way Types & Surfaces

Way Types

28.6 km

11.3 km

1.21 km

190 m

< 100 m

Surfaces

37.8 km

3.39 km

121 m

Elevation

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

Highest point (440 m)

Lowest point (20 m)

Weather

Monday 31 August

18°C

14°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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Bay Overlook – Skyline Boulevard loop from MacArthur

Bay Overlook

Skyline Boulevard

Huckleberry Botanic Regional Preserve Upper Pinehurst Entry

Skyline Blvd

Skyline Gate Redwood Regional Park

Shepherd Canyon / Montclair Railroad Trail

Snake Road bridge (Montclair/Shepherd Canyon)

Linda & Rose Avenue Park

Nearby routes

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