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Routes
Road cycling routes
United States
California
Alameda County
Oakland

Oakland Loop

Moderate

4.7

(3729)

12,650

riders

Oakland Loop

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:

Sibley Volcanic Regional Preserve

Waypoints

A

Start point

Train Station

Get Directions

1

16.0 km

Tidal Canal, Oakland — SF Bay Trail

Highlight (Segment) • River

Tidal Canal is a man-made trench dug 1889-1903 along the former San Antonio Creek to connect San Leandro Bay with the Oakland estuary and create more ship building and water …

Tip by

2

37.8 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.

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3

50.3 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 …

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B

65.5 km

End point

Train Station

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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

Elevation

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

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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Frequently Asked Questions

How long does it typically take to complete the Oakland Loop?

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.

What is the difficulty level of this cycling route?

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.

What kind of terrain will I encounter on the Oakland Loop?

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.

What are the best viewpoints or landmarks along the route?

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.

Does the Oakland Loop connect with other trails?

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.

What is the best time of year to cycle the Oakland Loop?

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.

Where can I park to access the Oakland Loop?

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.

Are there any permits or fees required for cycling the Oakland Loop, especially within Anthony Chabot Regional Park?

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.

Are dogs allowed on the Oakland Loop cycling route?

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.

Are there cafes or places to refuel along the Oakland Loop?

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.

Is the Oakland Loop suitable for beginner road cyclists?

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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