5.0
(4)
83
riders
11
rides
Gravel biking around Lake Sherwood, California, offers routes through the scenic Santa Monica Mountains and the Conejo Valley. The area features a mix of natural open spaces, watershed mountains, and both paved and unpaved surfaces suitable for gravel cycling. Riders can expect varied terrain, including canyons, hills, and trails that connect to a wider network of outdoor pursuits. The landscape is characterized by sparkling waters reflecting surrounding hills and lush greenery.
Last updated: May 29, 2026
5.0
(2)
28
riders
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
18
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9
riders
65.7km
04:36
1,200m
1,200m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
19.3km
01:23
220m
220m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Sycamore Canyon is really beautiful this time of year (January). There were 7 creek crossings to navigate, so expect wet shoes and socks if you do the entire length of the trail.
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The trail is packed dirt and perfect for gravel riding. You get nice views of the hills, and there are a ton of connector trails to explore from this gateway to Thousand Oaks.
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Pick up the Wendy Trail from hear and head off into the Boney Mountain State Wilderness. There are miles and miles of trails to explore, so take your pick and enjoy your run.
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The Wood Canyon Vista and Backbone Trailhead has a picnic table and water source. There are no reliable water sources along the trails, so make sure you are prepared before starting.
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Pedalers Fork is a unique combination of a restaurant, bar, coffee shop, and boutique bike shop in the heart of Calabasas. It offers delicious farm-to-table dining and artisan coffee with a casual vibe and a great patio, making it a fantastic place to relax after a ride.
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Cheeseboro Canyon Trailhead features a parking lot, toilets and a water fountain.
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Beautiful area, green everywhere
5
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At the end of Victory Blvd is a parking spot (USD 3 per car). From here you can choose wide trails and small paths throughout a hilly landscape. From top of the hills you can enjoy the view.
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Gravel biking around Lake Sherwood, California, offers a diverse landscape within the Santa Monica Mountains and Conejo Valley. You'll encounter a mix of natural open spaces, watershed mountains, and both paved and unpaved surfaces. Routes often navigate through canyons, hills, and open space trails, providing varied terrain for different skill levels.
While many routes in the Lake Sherwood area feature significant elevation gain, there are options for moderate skill levels. For a less strenuous ride, consider the Native Garden β Rancho Potrero gravel road loop from Casa Conejo. This route covers 11.9 miles (19.2 km) with a moderate difficulty grade, making it a good choice for those looking for a more accessible gravel experience.
The Lake Sherwood area is rich in natural beauty. You can explore various peaks and viewpoints, such as Sandstone Peak and Inspiration Point, which offer panoramic views. The region also features impressive canyons like Deep Ridge Open Space and parts of the Backbone Trail, providing scenic backdrops for your ride.
Yes, many of the gravel routes in the Lake Sherwood area are designed as loops, allowing you to start and end at the same point. An example is the challenging West Potrero Road β Sycamore Canyon North climb loop from Westlake High School, which is a 40.9-mile (65.7 km) trail leading through canyons and along roads.
The gravel biking routes around Lake Sherwood are highly regarded by the komoot community, holding an average rating of 5.0 stars from over 4 reviews. Many riders praise the varied terrain, scenic views of the Santa Monica Mountains, and the well-maintained trails that offer options for different ability levels.
Absolutely. For experienced gravel bikers seeking a challenge, the Lake Sherwood area offers several difficult and longer routes. The Sycamore Canyon North climb β Old Boney Trail loop from Dos Vientos Open Space is a difficult 20.1-mile (32.3 km) path featuring significant elevation gain and rugged terrain. Another option is the Deep Ridge Open Space β Conejo Canyons Open Space loop from Thousand Oaks Grant R. Brimhall Library, a difficult 21.6-mile (34.7 km) route.
The Santa Monica Mountains and Conejo Valley generally offer pleasant conditions for gravel biking for much of the year. Spring and fall typically provide mild temperatures and clear skies, making them ideal. Winter can also be good, though occasional rain might affect trail conditions. Summers can be hot, so early morning rides are recommended during warmer months.
Yes, the region is known for its scenic vistas. Many trails provide opportunities for panoramic views of the surrounding hills and valleys. Specific highlights like Inspiration Point and Upper Sycamore Overlook are excellent spots to take in the expansive landscapes of the Santa Monica Mountains.
There are approximately 7 gravel bike routes detailed in the Lake Sherwood area guide, offering a range of experiences from moderate to difficult. These routes allow you to explore the diverse terrain of the Santa Monica Mountains and Conejo Valley.
Yes, several routes are known for traversing scenic canyons. The Sycamore Canyon North climb β Old Boney Trail loop from Rancho Sierra Vista/Satwiwa, for instance, navigates through canyons and offers impressive views of the open space, making it a popular choice among local gravel bikers.
The Lake Sherwood area, nestled within the Santa Monica Mountains, is home to diverse wildlife. You might spot deer, various bird populations including hawks and herons, and other small mammals. The natural open spaces and watershed mountains provide a rich habitat for these creatures, offering opportunities for wildlife viewing during your rides.


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