“An amazing loop with awesome views, technical switchbacks, brutal climbs, and fast downhills.”
— Sam Brotherton
This is a really fun trail that has a little of everything. Most people just do the New Millenium Loop part (roughly 12 miles in all), but I think the downhill section of the Las Virgines trail at the end is worth the two miles on a paved road that gets you back to the trailhead.
The whole thing sees a lot less traffic than you'd expect given its high quality and proximity to LA. It's nothing but long, flowing, smooth singletrack; with tremendous views of Calabasas and the surrounding hills. While there's not much in the way of obstacles, the trail is still pretty challenging due to the unrelenting climbs and very tight switchbacks in places.
Need to Know
This area bakes in the summertime. From May to August I'd recommend saving this for the early morning or evening, unless you're a lot less of a wimp than I am.
Take the Las Virgenes Road. Exit off the 101, head south, and park at the Bark Park on the left side of the road. There's a singletrack that heads up from the northern end of the dog park; this is the trailhead.
Follow this trail up some switchbacks, and after about a mile, hang a left at the signpost. Follow this lovely, mellow singletrack for another few miles down switchbacks and across a sometimes overgrown stream, until it meets up with a fire road. Take a right at the fire road and follow it uphill until you reach a paved cul-de-sac. Immediately take a left down some steep switchbacks and enjoy the ride to the bottom of the hill.
At the bottom of the hill there's a fork in the trail marked by a pretty ambiguous sign that says "TRAIL". Take a right - don't continue straight or you'll end up at another trailhead. Drink some water and grit your teeth; from here you've got a brutal climb to the top of the hill with lots of demoralizing false summits.
At the top there's a large water reservoir and a sign that says "CAUTION - STEEP SWITCHBACKS". They're not kidding - be careful down the extremely steep and tight switchbacks that take you down the other side of the ridge. Apparently only a small, steep ribbon of land was designated for public use here so they had to make the best of a difficult situation. If you're an experienced downhill rider have fun, otherwise drop a foot on each corner like I did.
At the bottom of this valley, you'll cross a road with a security checkpoint where people in fancy cars are entering the gated community this trail circles. Try not to get hit by a Bentley, and then climb to the top of another ridge. Navigate some more switchbacks, and then enjoy some welcome mellower terrain as you near the end of the New Millennium loop.
At around mile 11, you'll get to an unsigned fork in the trail. To get back to the Bark Park trailhead, take the right-hand option. If you're up for a little more fun, go left and bomb down the Las Virgenes downhill section. This is classic SoCal downhill singletrack, a little rockier and looser than the rest of the ride, but steep and really fast. After a few miles you'll see a sharp right turn that heads downhill; take this and it will drop you off on Las Virgenes Road. a few miles from the trailhead.