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Road cycling routes
United States
California
Alameda County
Oakland

Redwood Double Loop from North Oakland

Hard

5.0

(9686)

9,758

riders

Redwood Double Loop from North Oakland

04:01

75.7km

1,380m

Road cycling

If you're seeking a demanding road cycling adventure, the Redwood Double Loop from North Oakland offers a true test of endurance. This difficult route covers 47.1 miles (75.7 km) and climbs a substantial 4513 feet (1375 metres), typically requiring about 4 hours to complete. You will experience the cool, shaded embrace of towering redwood forests, especially along Redwood Road, providing a refreshing contrast to the challenging ascents.

Planning your ride, you should know that this route is a favorite among local cycling clubs for its rigorous climbs and rewarding descents. While primarily paved, some variations might include unpaved sections, so be prepared. Parking is generally available in North Oakland neighborhoods near the starting point; always check local signage for restrictions. This is a route best tackled when you are well-rested and ready for a sustained effort.

The Redwood Double Loop is notable for showcasing the diverse natural beauty of the East Bay. As you cycle, you'll pass through Anthony Chabot Regional Park, enjoying expansive views of the Oakland Hills and glimpses of the Upper San Leandro Reservoir. The route also features the Bay Overlook, offering a moment to pause and appreciate the scenic vistas that make this ride a classic in the region.

Last updated: April 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Anthony Chabot Regional Park

Lake Chabot Regional Park

Reinhardt-Redwood Regional Park

Sibley Volcanic Regional Preserve

Huckleberry Botanic Regional Preserve

Waypoints

A

Start point

Train Station

Get Directions

1

8.30Β km

Bay Overlook

Highlight β€’ Viewpoint

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

Tip by

2

15.2Β km

Old San Leandro Creek Stone Bridge

Highlight β€’ 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

3

22.2Β km

Redwood Road Along Upper San Leandro Reservoir

Highlight (Segment) β€’ Trail

Tip by

4

55.5Β km

Skyline Blvd

Highlight (Segment) β€’ 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

B

75.7Β km

End point

Train Station

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Way Types & Surfaces

Way Types

42.1Β km

30.5Β km

2.80Β km

253Β m

< 100Β m

< 100Β m

Surfaces

69.9Β km

5.81Β km

< 100Β 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 (440Β m)

Lowest point (20Β m)

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Weather

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Today

Friday 8 May

18Β°C

10Β°C

0Β %

Additional weather tips

Max wind speed: 23.0Β km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the best time of year to cycle the Redwood Double Loop from North Oakland?

The Redwood Double Loop is enjoyable year-round, but spring and fall offer the most pleasant conditions with mild temperatures and clear skies, perfect for taking in the diverse scenery. Summer can be warm, and winter may bring rain, making some descents slick. Always check the weather forecast before heading out.

Is this cycling route suitable for beginners?

No, this route is considered difficult and is not suitable for beginners. It features significant climbs and descents, including segments with steep gradients up to 12.7%. It requires very good fitness and experience with challenging road cycling.

What kind of terrain can I expect on the Redwood Double Loop?

The route is primarily paved, offering a mix of challenging climbs and rewarding descents. You'll encounter steady ascents like the 3-mile climb on Tunnel Road and fast, smooth descents on sections like Redwood Road. Some parts, such as Pinehurst, are described as twisty and fast, requiring caution.

Are there any notable viewpoints or landmarks along the way?

Yes, the route offers several scenic spots. You'll find great views at Bay Overlook and pass by the historic Old San Leandro Creek Stone Bridge. The Redwood Road Along Upper San Leandro Reservoir section provides beautiful views of the reservoir and surrounding redwood forests.

Where can I park to access the Redwood Double Loop from North Oakland?

While the starting point is North Oakland, specific parking details can vary. Many cyclists begin from various points in the Oakland Hills. Look for street parking in residential areas near the start of the loop, or consider parking facilities within nearby regional parks like Redwood Regional Park or Anthony Chabot Regional Park, keeping in mind any potential parking fees or time limits.

Does the route pass through any other well-known trails or paths?

Yes, this route intersects with or runs concurrently for sections of several other trails. Notable ones include the Bay Area Ridge Trail - 02 - East Bay, the East Bay Skyline National Recreation Trail, and the Russell Bicycle Boulevard, among others.

Are dogs allowed on this cycling route?

This route is primarily a road cycling loop on paved public roads and dedicated cycle ways like Skyline Blvd. While dogs are generally not permitted to run alongside cyclists on busy roads, specific regulations for dogs may apply in the regional parks it passes through, such as Redwood Regional Park or Anthony Chabot Regional Park. Always check park-specific rules if you plan to bring a dog into park areas.

Are there any permits or entrance fees required for the Redwood Double Loop?

The Redwood Double Loop primarily uses public roads and does not typically require a specific cycling permit for the route itself. However, if you plan to park within or access facilities in Anthony Chabot Regional Park or other East Bay Regional Parks, there may be parking fees or specific regulations to be aware of. It's always a good idea to check the East Bay Regional Park District website for the latest information on fees and rules.

What kind of wildlife might I see while cycling?

As the route winds through redwood forests and open hillsides, you might spot various local wildlife. Common sightings can include deer, squirrels, and a variety of bird species. Keep an eye out, especially in the quieter, more forested sections.

What should I bring for a ride on the Redwood Double Loop?

Given its challenging nature and length, you should bring plenty of water, energy snacks, a repair kit (including spare tubes and a pump), and appropriate cycling gear. Layers of clothing are recommended due to potential temperature changes between climbs and descents, and through shaded redwood groves versus open areas. A helmet is essential.

How long does it typically take to complete the Redwood Double Loop?

For an experienced racebike cyclist, the route typically takes around 4 hours to complete. However, this duration can vary significantly based on your fitness level, the number of stops you make, and your average speed on the climbs and descents.

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