4.7
(3729)
12,650
riders
03:24
65.5km
890m
Road cycling
Embark on the Oakland Loop for a road cycling experience that transitions from flat, scenic shorelines to challenging climbs. This moderate route covers 40.7 miles (65.5 km), with a substantial 2908 feet (886 metres) of elevation gain, and typically takes around 3 hours and 24 minutes. You will pedal along…
Last updated: April 23, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Train Station
Get Directions
16.0 km
Highlight (Segment) • River
Tip by
37.8 km
Highlight (Segment) • Cycleway
Tip by
50.3 km
Highlight (Segment) • Trail
Tip by
65.5 km
End point
Train Station
Way Types & Surfaces
Way Types
43.6 km
12.6 km
8.77 km
271 m
183 m
< 100 m
Surfaces
53.2 km
11.9 km
370 m
< 100 m
< 100 m
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Elevation
Highest point (420 m)
Lowest point (0 m)
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Weather
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Today
Saturday 25 July
23°C
14°C
0 %
Additional weather tips
Max wind speed: 24.0 km/h
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This route was planned by komoot.
This specific Oakland Loop, designed for racebikes, covers approximately 65.5 km and generally takes around 3 hours and 24 minutes to complete. This duration can vary based on your cycling pace and any stops you make along the way.
The Oakland Loop is rated as 'moderate' in difficulty. It includes significant elevation changes, with an ascent of about 886 meters, characteristic of routes in the Oakland Hills. While challenging, it's a rewarding ride for those with good fitness.
The route primarily features well-paved roads, typical for racebike cycling. You'll experience varied terrain, from steady climbs in the Oakland Hills, including sections of Skyline Blvd, to rolling sections offering panoramic views. Some parts may be exposed, especially on warmer days.
The Oakland Loop offers spectacular panoramic views, especially from the Oakland Hills sections. You'll pass highlights like the Tidal Canal, Oakland — SF Bay Trail, and ride along Skyline Blvd, which provides vistas of the entire central Bay Area, including Oakland, San Francisco, and the Bay.
Yes, the route intersects with several other paths. Notable sections include the San Francisco Bay Trail (11% of the route), the East Bay Greenway (4%), and the Shepherd Canyon / Montclair Railroad Trail (3%). You'll also encounter smaller segments of trails like the Goldenrod Trail and Skyline Boulevard Singletrack.
Spring and fall generally offer the most pleasant cycling conditions with mild temperatures. Summer can be warm, especially on exposed sections of roads like Pinehurst Road. While the views are stunning year-round, check the weather forecast for optimal riding comfort and visibility.
Specific parking details for this exact loop are not provided, but given its nature as a road cycling route encompassing various areas, you can typically find street parking in residential areas near the start or in public parking lots in Oakland. Consider starting near a park or a commercial area with available parking.
Generally, there are no specific permits or entrance fees required for road cycling on public roads and trails that make up the Oakland Loop. If your route takes you through Anthony Chabot Regional Park, standard park regulations apply, but typically there are no fees for cycling on designated paths within the park.
As this is primarily a road cycling route, dogs are generally not permitted to run alongside cyclists on the main roads for safety reasons. If you plan to stop at parks or trails that allow dogs, ensure they are on a leash and follow local regulations. This route is not designed as a dog-friendly trail.
Given that the loop passes through various parts of Oakland, including urban and suburban areas, you will find opportunities to stop for food and drinks. Consider planning your route to pass through neighborhoods like Montclair or Rockridge, which have a good selection of cafes and shops.
Due to its 'moderate' difficulty rating, significant elevation gain (886m), and 65.5 km distance, this specific Oakland Loop is generally more suitable for intermediate to experienced road cyclists. Beginners might find the climbs challenging. Shorter, flatter routes along the Bay Trail or Lake Merritt Loop might be better starting points for new cyclists in Oakland.
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