Mishe Mokwa & Backbone Trail Loop
The Mishe Mokwa and Backbone trails are all part of the Santa Monica Mountains National Recreation Area. Combine both trails, and you a have a great loop that includes sites you may have heard of: Sandstone Peak (highest point in the Santa Monica Mountains), Tri-Peaks, Inspiration Point, and Balanced Rock.
The full loop will be a little over 6 miles of hiking with about 1600 feet of elevation gain. You can see a map of both trails by clicking HERE. If you're going to do the full loop, I'd recommend starting the hike from the Mishe Mokwa Trailhead, explore Tri-Peaks (an additional 1 mile roundtrip), check out Sandstone Peak, and then complete the loop along the Backbone Trail. Tri-Peaks has many unique rock formations and cliff edges to explore. On a clear day, you can even see some of the Channel Islands from Tri-Peaks and its much, much less crowded than Sandstone Peak. Hiking out to Inspiration Point and Balanced Rock aren't worth it to me.
For a shorter hike, Sandstone Peak is still pretty cool. Start at the Sandstone Peak Trailhead and hike straight up. I promise you'll feel like you've worked your legs a bit and the views up top will definitely be enjoyed. The Sandstone Peak hike will be about 3 miles round trip.
You can get lost if it's your first time there, so print and bring the map linked above.
I'd highly recommend watching the sunset at Sandstone Peak, especially if there's a few clouds in the skies. Be sure to take a headlamp, water and a phone, and don't hike alone at night. There are mountain lions that live in the area, but they normally don't bother anyone.
Pack some food and treats to enjoy while you take in the views.
If it recently rained, check out the Grotto Trail that starts directly across the street from the Sandstone Peak Trailhead. There's a cave and a cool rock formation surrounded by water. It's 3.5 miles round trip. This trail is also on the map linked above.