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Road cycling routes
United States
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St. Louis County

Oakland

The best road cycling routes around Oakland

4.8

(73)

1,551

riders

87

rides

Road cycling routes around Oakland offer a diverse landscape, ranging from flat urban paths to challenging climbs in the rolling hills. The region features significant elevation gains in areas like the Oakland Hills, alongside tranquil redwood forests and panoramic views of the San Francisco Bay. This varied terrain provides options for different cycling preferences, from leisurely rides around Lake Merritt to demanding ascents on roads such as Tunnel Road and Skyline Boulevard.

Best road cycling routes around Oakland

  • The most…

Last updated: August 17, 2026

4.5

(4)

70

riders

#1.

Gravois Greenway and River des Peres Greenway Loop

35.8km

01:33

160m

160m

The Gravois Greenway and River des Peres Greenway Loop offers a delightful road cycling experience, weaving through a mix of tree-lined paths and urban landscapes. You'll find yourself cruising along…

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Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

The Kirkwood Train Station – Woods Avenue Scenic Road loop is a demanding road cycling adventure that will test your limits. You'll navigate a varied terrain, with mostly well-paved surfaces…

Hard
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Popular around Oakland

Hiking around Oakland

Cycling around Oakland

Running Trails around Oakland

Tips from the Community

Bckr
November 2, 2024, Grant's Trail at Grant's Farm

Stop and smell the horses

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j3f12
June 2, 2024, Melrose Road

Great scenic ride through rolling hills

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Scenic ride on Woods Avenue through the woods. Moderate climb if you’re going Eastbound, downhill otherwise.

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Fun downhill ride

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j3f12
April 15, 2024, Pierside Lane

Tree-lined street with bike lanes

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j3f12
April 14, 2024, Hamilton Carr Trail

Beautiful bike path

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Scenic stretch of Grant’s Trail. Also, there are way fewer roads crossing here than on the parts further up to the Northwest.

0

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Grant's Trail is one of the best bike trails in the STL area.

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Frequently Asked Questions

How many road cycling routes are available in Oakland?

Oakland offers a wide selection of road cycling routes, with over 80 tours available. These routes cater to various preferences, from leisurely rides to challenging climbs.

What kind of terrain can I expect on road cycling routes in Oakland?

Oakland's road cycling terrain is incredibly diverse. You'll find everything from flat, urban paths around areas like Lake Merritt and the Bay Trail, to significant climbs and descents in the Oakland Hills. The region also features tranquil redwood forests and routes with panoramic views of the San Francisco Bay.

Are there challenging climbs for experienced road cyclists in Oakland?

Yes, the Oakland Hills are a major draw for experienced cyclists seeking challenging climbs. Roads like Tunnel Road, Skyline Boulevard, Joaquin Miller Road, Redwood Road, and Pinehurst Road offer substantial elevation gains, sometimes over 800 feet on a single climb, providing both a demanding workout and rewarding views.

Are there easy, flat road cycling routes suitable for beginners or relaxed rides?

Absolutely. For those seeking a more relaxed experience, Oakland offers many easy, flat routes. The 3.4-mile path around Lake Merritt is perfect for a gentle ride, as are sections of the Bay Trail and routes along the Oakland Estuary and Jack London Square. Over 35 easy routes are available in the region.

What scenic views can I expect on road cycling routes in Oakland?

Many routes, particularly those along Skyline Boulevard and the Bay Trail, offer panoramic vistas of the San Francisco Bay, including the city skyline. Cycling through areas like Redwood Regional Park provides unique views of ancient coast redwoods, while routes in Joaquin Miller Park offer views of downtown Oakland.

What do other cyclists say about road cycling in Oakland?

The road cycling routes in Oakland are highly rated by the komoot community, with an average score of 4.7 stars from over 70 reviews. Cyclists often praise the varied terrain, from challenging hills to scenic bay views, and the opportunity to ride through redwood forests.

Are there any notable landmarks or attractions along the road cycling routes?

Yes, several routes pass by or near interesting landmarks. You can cycle past the urban estuary of Lake Merritt, a National Historic Landmark, or explore areas like Joaquin Miller Park, known as the 'jewel of the hills'. Some routes also offer views of the Emerson Grand Basin or the Laumeier Sculpture Garden. The River des Peres Greenway is also a popular cycling highlight.

Can I find loop trails for road cycling in Oakland?

Yes, Oakland features numerous loop trails for road cycling. Many routes in the Oakland Hills, such as the Pinehurst Loop (often starting from Tunnel Road and following Skyline and Redwood Roads), are designed as loops, allowing you to experience diverse scenery without retracing your path.

What is the best time of year for road biking in Oakland?

Oakland generally offers good cycling conditions year-round due to its mild climate. Spring and fall often provide the most pleasant temperatures. Summers are typically warm and dry, while winters are mild but can bring rain. Always check local weather forecasts for current conditions.

Are there family-friendly road cycling options in Oakland?

Yes, Oakland has several family-friendly road cycling options. The flat, paved path around Lake Merritt is ideal for families, as are many sections of the Bay Trail which offer scenic, car-free riding along the waterfront. These routes provide a safe and enjoyable experience for all ages.

Where can I find parking for road cycling trails in Oakland?

Parking availability varies by location. For routes in the Oakland Hills, designated parking areas can often be found near park entrances or trailheads, such as those for Redwood Regional Park or Joaquin Miller Park. For urban routes like Lake Merritt or the Bay Trail, street parking or public garages in nearby commercial areas are typically available.

Are there any road cycling routes that pass through redwood forests?

Yes, you can experience the unique tranquility of redwood forests on your road bike in Oakland. Redwood Regional Park, located within the Oakland Hills, features impressive stands of coast redwoods. Cycling through these dense groves offers a serene experience, feeling far removed from the city.

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