Sycamore Canyon is one of the my favorite places to bike in the Santa Monica Mountains, and I'm not the only one. The two main trail heads are in Thousand Oaks in the north, and off the PCH at Sycamore Cove on the coast. I usually take the main fire road that runs south through Point Mugu State Park, and then branch off and explore some of the less-travelled back-country areas
There's some breath-taking views, technical downhills and heart-pumping hills, and maybe a few rattlers, coyotes and bobcats if you're lucky! Even though it's a popular area, there's enough trails that you can easily for hours without seeing anyone once you're off the fire-road. I've mapped out my favorite routes on Google, but if you don't know the area I'd recommend buying a commercial map, such as the Tom Harrison's for Point Mugu or the National Geographic's for the Santa Monica Mountains.
Starting from the north, you have a couple of choices for parking lots in Thousand Oaks. I prefer the dirt parking lot at the south end of Wendy Drive, which is free, easy to reach from the 101, and has a nice single track over to the main fire road. You can also park in the Rancho Sierra Vista/Satwiwa parking lot, which is right next to the start of the fire road.
The road is paved for the first few miles, and quickly heads downhill on a section known universally as the Asphalt Hill. Going down is fun, but as I learnt on a hot August afternoon when I was fresh off the boat, make sure you have enough water for the return or you'll get heat-stroke! At the bottom of the hill, it's a lot more wild, with a great section running through oak groves, gently downhill along the side of the creek.
The first big junction you'll reach is with Ranch Center Road. The main fire road continues straight, and you branch off to the west to get to Ranch Center. The road is roughly paved, and has some decent uphill sections, followed by a great downhill to the old ranch buildings that led to its name. From there, you can take Wood Ranch trail back to the main fire road, and also get access to a lot of other side-trails.
You can either take the main fire road south for a couple of miles, or take some single tracks on the other side of the creek that parallel it, and join up again by the Wood Canyon junction. The first single track is Sin Nombre, recently opened to bikes, and so-called because it's never had a name on its sign. There's some fun technical sections, and it leads onto Two Foxes, a similar single-track.
From the junction of Wood Canyon trail and Sycamore, you can take the fire road three miles down to the beach. It's a pretty gentle downhill, but in the rainy season you've got about a dozen stream crossings to navigate.
Off Wood Canyon, there's one of my all-time favorite trails, Guadalasca. Built about 15 years ago by my friend Frank Padilla, it's a sweet single track snaking up the mountain, with some great views and lovely switchbacks. Watch out for some patches of poison oak towards the top.
As an alternative for the hard-core, you can take Hell Hill up to the same Overlook Fire Road that Guadalasca connects with. As you might guess by the name, it's not for the weak-hearted. An exposed, steep fire-road, it doesn't take any prisoners.
Once you're on the Overlook road, you can take that down almost to the beach, and meet up with the main Sycamore fire road, or there's another challenging single-track you can take instead. Wood Canyon Vista trail is rocky and technical, with a lot of great views over the canyon as the name suggests.
There's a lot more single track trails that I haven't listed, but those are my favorites. Be careful not to take any trails heading east from Sycamore fire road, that whole area is a protected wilderness with no bikes allowed. Most of the trails have steps, close brush or other obstacles so biking them would not be much fun anyway.
If you want a gentle ride without anything technical, I'd recommend starting at the beach end, taking the fire road to the base of the Asphalt Hill, and taking the same way back.
For a bit more of a workout, with some mildly technical sections and decent uphills, start at the TO end, turn onto Ranch Center Road, take Wood Canyon, and then the main fire road back to the trail head.
More hard-core bikers will get a kick out of the Ranch Center-Guadalasca-Wood Canyon Vista-Two Foxes-Sin Nombre loop. This gives you some solid elevation gain, and a lot of technical single-tracks.
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