“An amazing loop with awesome views, rugged switchbacks, brutal climbs, and great downhills.
— Sam Brotherton
This is a really fun trail that has a little of everything. 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, 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.
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 run 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 are 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. Make sure to watch your step.
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 Millenium 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. In less than a mile you'll be back at the juntion where you initially took a left to start the loop.