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Oakland Crest Sidewinder (auto-free)

 3.0 (3)

Maximum singletrack with minimal climbing in the Oakland Hills.

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1,423' 434 m


161' 49 m


2,715' 827 m


2,734' 833 m



Avg Grade (2°)


Max Grade (16°)

Dogs Unknown

E-Bikes Unknown

Features Views


This is a point-to-point ride made possible by the Bay Area's awesome mix of parks and rapid transit. The cherry of this ride is the long mellow singletrack segment in the median of Skyline Boulevard, which also has nice views. It is also an opportunity for people mountain biking to be viewed by the general public. The curving Towhee singletrack is the second highlight.


Starts at Rockridge BART. Alternately, you can start at Ashby BART if on the Richmond line if you want to save the transfer hassle. Adds about two miles and little to no time.

Climbs on pavement mostly via a mix of cycling lanes, cycletracks, paved paths, and roads with few motorists. It generally follows the former Sacramento Northern electric interurban rail route. The paved path segments are on the rail bed itself.

The dirt starts at the Skyline Gate in Redwood Regional Park and does not stop for 20 miles. It roughly follows contour on West Ridge Trail, Castle Park Trail, and Sequoia Bayview Trail with the steepest parts connecting the the first two. The connector from Sequoia Bayview Trail back into Redwood Regional Park is a nice drop with a quite technical short bit of high timbered steps. There are various ways across to the south edge of Redwood Park from here. Angling left hits Dunn Trail, which makes the most of the bit of elevation loss. If you miss that turn though any of the routes ahead end up where you need to go.

A short jog right on Redwood Road hits Skyline Boulevard. Turn left on Skyline on the trail in the median. The median is narrow here and the trail is just along the northbound left turn lane of the road. So take your time and pick your moment to make the turn as the motorists waiting in the lane may think you are about to ride the wrong way in the lane. You are not though. Rather, you hop the curb almost at the point of the median and hit the trail.

From here, it is a fun 3.5 miles of singletrack. As stated in the description of that trail, there are periodic road crossings via curb hops. Take your time to look forward and back to check for motorists that might potentially turn to cross over the median at these locations. You do not have the right of way. Just past halfway along this segment the more obvious trail drops right down to the street. This connects to the top of Artemisia in the adjoining Leona Canyon Regional Preserve, which provides a means to short the ride and out to Coliseum BART. That misses the most downhill part of the Skyline Boulevard median singletrack though. To stay on the ride and hit that, take the less-worn and obvious left fork where the trail drops right. It seems like this will put you head-on into northbound motorists, but the trail turns again with a reasonable buffer from the road.

Eventually, the Skyline median ends and you cross over the southbound lanes to a fire road to the west of Skyline Boulevard. A bit less than half a mile ahead look for the Chabot Equestrian Center. This is a decision point. The ride laid out heads on to cut over the canyon to the east to pick up more singletrack. Or you can stay on the fire roads and trails along Skyline Boulevard and head for San Leandro or Coliseum BART via one of various possible routes.

To continue on this ride though, cut left off the fire road and cross the northbound lane of Skyline Boulevard to the entrance to the Equestrian Center. Then turn right on the singletrack. This goes down to the Goldenrod Trail. Simply follow the route laid out or find your own. If you follow the route, just two potentially tricky bits come to mind. Lower Redtail Trail connects to Upper Redtail Trail via a crossing Marciel Road. The road is wide here with parking areas and turnouts on both sides and the trail connection is unmarked. Just forge ahead with confidence and you'll pick up the trail entrance on the far side. The other tricky bit is the bridge crossing over an inlet to Lake Chabot. It is narrow between the handrails. And the width varies. More fun to turn right just ahead of the bridge and cross the inlet on ground. It is dewatered in the dry time of year and only bottom bracket, not axle, deep most others.

One of the best parts of riding auto-free via rapid transit is getting to leave it all on the trail without having to regain coherence for driving. Rather collapse into BART and enjoy the high.


Shared By:

Preston Jordan

Trail Ratings

  3.0 from 3 votes


in Berkeley


  3.0 from 3 votes
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29 Views Last Month
4,016 Since Jul 20, 2019



My 'home trails' are short but sweet!
Jul 24, 2015 near Piedmont, CA
Misty morning at Miller Park, Saturday 9th Sept.
Sep 12, 2017 near Piedmont, CA
Upper Towhee Trail.
Aug 19, 2016 near Castro…, CA
Lower Towhee Trail.
Aug 19, 2016 near Ashland, CA
Jul 8, 2018 near Ashland, CA
Redtail Trail leadoff from Brandon Trail
Nov 24, 2015 near Castro…, CA


Current Trail Conditions

Add Your Check-In


Apr 21, 2020
James King
Mar 28, 2020
David Ngov
fun 27.7mi
Feb 8, 2020
Steve Cujo
Old eyes and a tiny GPS. So I missed a turn, and didn't do the entire route - but it was a nice ride. 22mi
Oct 20, 2019
Grant Oakley
Fun but crowded 27mi — 3h 00m