Take Main St. toward 17. Go right on Kennedy. Wind and weave about 2 miles on the road-mostly up hill. You will get to a trailhead on the left - there are is very limited parking here so you can try it but I usually park downtown and bike up there.
Summary: This trail is extremely boring with no pay off. And by "pay off" I mean all you get is a climb: no single track, no technical... nothing. The only good thing about this trail, and the entire trail system out here, is that 1) it's a grueling climb and 2) it doesn't close in the rain. I guess if you are into this kind of cardio stuff, it's good.
This trail is as easy or as hard as you make it. If you go at a Turkey Day Group Ride pace, it is very easy. If you're trying to break a Strava record, it's hard.
My local Santa Teresa County Park does close in the rain, so this is the alternative to road riding. Leave your full suspension all mountain bike at home, it isn't necessary for Kennedy, and in fact, a CX bike is the best tool for this job, because all it really is is a "dirty road ride". Integrating this trail into an epic 'cross ride could be cool... but for a true MTB trail I just say "meh".
People like this trail due to the fact that it doesn't close, or maybe they may live by it... but ultimately there are Strava climbing records to break, especially DogMeat. I guess if you're into all that, this is great, but personally I hate climbing if there isn't going to be at least one "fun" section to play with. when I ride this trail, I feel like I'm on a hamster wheel.
Unfortunately I have to give it a "2" for the boring factor. Unless the other trails are closed, it isn't worth riding this, especially on a mountain bike. CX bike, maybe.
Recommended Route: Start at the bottom, point your bike upward, and start pedaling.
Other recommended trails in the same area: Santa Teresa County Park
Summary: This trail is good for training. If you only have one day to ride and have fun, this is not the trail. Go elsewhere like Saratoga Gap or Skeggs. Uphill is very hot (summer time/no shade), long and can be steep at times. Downhill has loose rocks and very shady. Make sure to bring your clean lenses because it get real dark when going to dog meat. I think that's what they call that single track trail.
4 for aerobic: because towards the end the are two killer climbs. At least for me when using 32/32 gearing.
3 for technical: Only when descending. Tons of loose rocks and steep descend.
3 for overall rating: This is not a trail you want to go on a weekend with your friends/family. This is the trail you go on, on a weekday for training. Up or down, it's not fun. This is just like Mission Peak but a little easier.
Other recommended trails in the same area: Steven's Canyon
Canada de Oro
Summary: Great training ride, no matter how you climb to the top of Sierra Azul. Boring, yes, but, sometimes when you're training, you gotta take your medicine, no matter how boring the ride may be. Just do it.
Recommended Route: 1. up from kennedy, to the top of priest rock, hang a right and grab your nuts...go right on limekiln or straight down priest rock, both dump you on alma bridge road, by lexington reservoir. ride back to your car.
2. up from kennedy, same as above, go past priest rock, ride along the ridge an additional mile or so to the limekiln/woods trail/powerpoles junction, from here, you can go right on limekiln, bomb down to lexington, or, if you want to really put in some mileage: go left on woods, down to the top of hicks, cross the road to quicksilver, now ride back down to either the mockingbird entrance or, the hacienda entrance, ride home or back to your car along almaden road to camden, to shannon, to kennedy trailhead.
3. start from lexington and, from the limekiln gate (SA 1 I think? ) climb: limekiln to woods/kennedy junction (5+miles of climbing) to the top go left and take kennedy trail along the ridge, to the top of priest rock, go left, go down priest rock, go right on limekiln, back down to where you started.
Other recommended trails in the same area: Stevens Canyon, Montebello, Long Ridge, UCSC, Santa Teresa
Summary: When most people go to this trail and try it for the first time, they either throw the bike off a cliff or come back. Let's be real honest here people, this trail is damm hard on the way up. The climbs makes you want to tap unknown sources in your body and use that energy to kick your so-called friend in nutz. Try many different styles going up such as; don't go to granny gear (stay in middle front chainring) and see how far you can go. Try just regualar riding and make it up without stopping. Or like many crazy dudes out there- single speed it up. Whatever you do= have fun and watch your speed= lots off camber turns that will push you into a berm, Speed contol and brake work will get you back down.
Summary: After rain ride: Kennedy has been reviewed to death but I would like to add that Kennedy trail has a reputation of maintaining good condition after a rain since the soil is so rocky and the pitches so steep. Kennedy lived up to its reputation today. The National Weather Service reported that the Sierra Azul area got 0.2 to 0.5 inches of rain last night. I rode up Kennedy today (blue sky, 55deg F)and the trail was perfect: grippy and very few soupy sections. The bottom line was that at the end of the ride there was little to no dirt or mud on my drive train, and that helps the wallet in the long run, right?
Saw a cyclocross dude and a freakin' single speeder climbing Kennedy. WTF? Skillz!
I give it a 5 for aerobic difficulty due to the "Wall" near the Kennedy-Priest Rock junction. There are more "walls" if you continue up the ridgeline past Priest Rock towards the power poles. If you clean all those walls between the Priest Rock and Limekiln trail junctions, hats off to you.
Other recommended trails in the same area: Belgatos!