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Length 13 miles
Time 3 hours
Total Climb 2500 feet
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Skyline Trail

Skyline Trail is a roughly 6-mile-long trail that closely follows Skyline Boulevard heading southeast from Saratoga Gap, and presumably takes its name from that road. Most of the trail is singletrack though there are at least two sizable fire-road stretches that are hard to miss. As you might expect from a trail that closely follows a ridgetop road, Skyline Trail involves relatively limited net elevation change along its length. If you don't count the side loop around Summit Rock Loop Trail, this entire ride takes place within a 400-foot range of elevation. When you also consider the fact that parts of the trail have enough moderately technical features to keep even experienced riders entertained, it should come as no surprise that doing even just this one trail as an out-and-back route would result in a fun and reasonably substantial ride, which is exactly what the ride you see on this page does. For those who want more, Skyline Trail even presents a couple of good extension possibilities. It would have been even better if some of those extensions could be used for loops, but that's not the case at the time I write this. (More on that below.)

If Skyline Trail enjoys less renown than it deserves among mountain bikers of the Peninsula and the South Bay (though I'm not sure that's necessarily true anymore), it might be because its availability for biking is a relatively recent development. During a ride I did here on June 2015, a printed notice announcing the change in access rules to allow bikes on Skyline Trail was still posted at one of the trailheads. The part of the trail that passes through Castle Rock State Park had been opened to bikes a year or two before that, actually. To read a bit more of the history behind this trail and of bicycle access in Sanborn County Park, refer to the text of my Sanborn County Park ride. At the time I write this, the opening of this trail to bikes constitutes the most major development in recent years in terms of bike access along the entire Route 35 corridor, in my opinion.

I've mentioned that the trail follows Skyline Boulevard closely. That's not an approximation. Skyline Trail is never more than a quarter mile away from Skyline Boulevard even at its most widely separated spot, and you spend the vast majority of your time on this ride within shouting distance from the road. If this makes you think that you'll never be free from traffic noise on this ride, you are correct. This is not a ride on which it will be easy to pretend that you're deep in the bosom of nature. It's not like the traffic noise is constant, but it's not infrequent either. And, on weekends, it's never too long before some sports bike rider or two whiz past you on Skyline Boulevard with engines running at the top of their rev range.

On the positive side, however, the presence of traffic noise won't be enough to hurt your enjoyment of this ride very much, because the trail is such a nice one. Leaving aside the parts of Skyline Trail that follow pre-existing fire roads, most of the trail is a smooth, first-class, hillside singletrack. There are just enough roots and technical features scattered along the trail to keep things interesting. None of these are very challenging, though they're probably still enough to cause suffering for fresh beginners. Perhaps one or two of the trail features may deserve the attention of experienced riders too, but the rest are merely adequate to hold their interest, if you ask me. If you're familiar with Saratoga Gap Trail, you can consider yourself already familiar with the character of the singletrack portions of Skyline Trail, because the two are identical twins in terms of setting, attitude, and character, which is no surprise since these trails are essentially a continuation of each other.

Even if Skyline Trail were not as fun as it is, this ride would still be far from boring. For a trail that "simply parallels a road", there are a lot of variations that come your way along this trail. You switch back and forth between a fire road and singletrack a few times, as I already mentioned. There is also a fork where the trail splits into two and reconnects before too long (though one side of this is only for hikers, unfortunately). You find yourself on Skyline Boulevard at one point and need to ride along the road for a few hundred feet before you can return to trails. (The hiking-only option at the split I just mentioned actually avoids this road segment, but riders don't seem to have any option that does.) The trail also takes you through at least three trailheads, two of which are fairly busy staging areas on weekends; one for Summit Rock and the other near the main entrance of Castle Rock State Park.

I've also added a little bit more to this variety by including in the ride what is currently the only bike-legal loop possibility along this trail. This is the small loop you see near the middle of the route, formed by taking Summit Rock Loop Trail on your way back. I must say that this is not a very desirable option and I've only included it on this ride to show what to expect to those who might be curious. This detour via Summit Rock Loop Trail is purely a fire road and it takes you down into the big dip you can see centered at the 10-mile mark of the elevation profile plot, out of which the climb is not gentle. So, it will really only make sense to those who are really curious or those who are looking for a tougher challenge. Omitting that section and returning via Skyline Trail would save you nearly 250 feet of elevation gain, though your savings in mileage will be barely more than a quarter mile.

One word of caution I would add is about mosquitos. With the possible exception of the winter months, any time you do this ride on a warm day, you'll usually be surrounded by a swarm of mosquitos as you ride. The only exceptions to this will be the portions where you'll be maintaining a decent speed and perhaps those stretches that are exposed to the open sky. In my experience, even being covered in insect repellent isn't enough to prevent these annoying creatures from hovering in front of your eyes on such days, though it may help prevent actual bites and may serve to reduce their numbers a little bit. My best advice for avoiding them altogether is to reserve your plan to do this ride for a day when the temperatures will be no higher than 65 degrees.

If you like what you find on this ride but want some more, you will find options to extend this route both at its upper end and at its lower end. At the southeastern end of this route, half a mile before the turn-around point of this ride, John Nicholas Trail splits from Skyline Trail. If you follow John Nicholas, you will have about a three-mile, smooth singletrack descent, that is as along as you can afford the 1100 feet of extra elevation gain you need to cover when climbing back up the same three miles. You can take John Nicholas even all the way to Black Road, an extra two miles, though that part is a less interesting fire road. More extensive options for additional mileage are available at the northwestern end of the route, right where you begin the ride. If you simply cross Route 9 and get on Saratoga Gap Trail, you can follow it all the way to Long Ridge or (if you have superhuman stamina) all the way to Skyline Ridge and Russian Ridge without interruption. My personal recommendation for anyone who wants a little bit more of the same but doesn't want to make the ride too challenging would be to opt for Saratoga Gap Trail but to turn around where it connects to Long Ridge Open Space, because the portion of that trail up to that point doesn't have much net elevation change, allowing you to turn back wherever you feel like you've had enough, without having to incur too much climbing over your return.

© Ergin Guney


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