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Length 29 miles
Time 3 hours*
Total Climb 3100 feet
Fun Rating
Scenic Rating
Aerobic Difficulty
Technical Difficulty 
* On a road bike

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Skyline Loop
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This ride is a medium-length road loop through a good mix of the scenic roads available in the East Bay. This includes roads that follow tight canyons, ridgetop drives with wide-open views of the bay, passing through a redwood grove, and various flat and sloped stretches flanked by oak woodlands. I would classify this ride as providing a disproportionately high amount of scenery in return for the amount of climbing that you'll have to put in. It's not that there isn't a significant amount of climbing on the ride—there is. It's just that there's not enough to label this ride as "a climb" as a matter of its core character (as you would for a ride up Mount Diablo or Mount Hamilton, for instance).

Since the route passes through plenty of populated areas, there could be any number of places from which this ride can be started. For one thing, this ride would be feasible for many residents of the East Bay as an out-the-door ride option, making their own home the best starting point. For those who will be coming from elsewhere to do the ride, starting from "downtown" Orinda, the way I did in this case, is aimed mainly at ending up at a cute place with options for food and drink as soon as I have completed the ride, as I usually prefer to do. Another reasonable option could be to start it from the parking lot of Tilden Park at "Inspiration Point". There aren't any amenities immediately around it, but at least it's a free parking lot of moderate size (though it still fills up very quickly on weekends) and is a bit scenic. There are a number of other free parking lots available in Tilden Park, though most aren't larger than the one at Inspiration Point, as well as a couple of other recreational area parking lots elsewhere along the ride route, like a sizable lot for Redwood Regional Park. Probably the option that would give you the best possible choices for a post-ride bite would be to start and end the ride near Berkeley's Gourmet Ghetto, at least if you're confident that you won't get lost as you try to make your way from there to the ride route through the bewildering, twisty maze that is the street network of Berkeley Heights.

If you do decide to start the ride from Orinda, notice that the Suggested Parking link on the left is pointing merely at street parking in the downtown area. These parking spaces are subject to time limits on weekdays, but are unlimited on weekends.

One decision to be made about this loop (as with any loop) is whether to do it clockwise or counter-clockwise. My excuse to do it clockwise was the intention to descend rather than climb the steepest stretch of the route, which is the nearly 1.5-mile section on South Park Drive in Tilden Park. The overall average grade of this road is just under 10%, but the figure actually hovers above 12% (and not infrequently exceeds 15%) in its steeper upper half. If you're okay with covering that part of the ride in the uphill direction, it might actually be preferable to do the ride counter-clockwise, because this would put you on the downhill side of the road along all the scenic stretches, giving you more open views.

The first leg of the route on Moraga Way is a wide and gently curving road through spacious suburban lands. The road appears to be popular with motor-vehicle traffic, but there is a good bike lane throughout this stretch of the ride, so the traffic will be of little concern to you.

Your first opportunity to leave civilization behind arrives once you turn onto Canyon Road, though only after that road passes through a brief stretch of suburban neighborhoods as well. When you do leave developed areas behind, this road has very little traffic, which is a blessing since it has no bike lane and no significant shoulder space. That situation doesn't change when you continue onto Pinehurst Road as it takes you initially up a gentle and scenic climb zig-zagging up the side of a ridge, before quickly descending down the other side of the same ridge. It's no wonder that much of the traffic I encountered on this road consisted of motorcyclists who were seemingly out for pleasure cruises.

Redwood Road, true to its name, takes you through a short segment along the bottom of a narrow canyon, surrounded (sometimes quite densely) by redwood trees. This is the portion of the ride with the lushest greenery. It also happens to be the part of the ride where the longest climb of the loop starts. The slope is almost unnoticeable in the beginning, but it keeps steepening all the way to the end of this 4-mile, almost-unbroken climb, although the grade rarely exceeds 10% even in the steepest stretches near the end of this segment.

Unsurprisingly, Skyline Boulevard presents some nice views of the bay from here and there. You catch your first glimpses across the water almost as soon as Redwood Road lifts you onto Skyline. You'll also encounter some traffic on Skyline for the first time on the ride since Moraga Way. A lot of Skyline Boulevard (at least other than the stretch where it goes around Joaquin Miller Park) looks more or less like a suburban street in any hillside neighborhood. Things start looking more like open space and less like a neighborhood once you turn onto Grizzly Peak Boulevard. Moreover, if Skyline is scenic, then Grizzly Peak is doubly so. The portion of the ride on Grizzly Peak also includes the last significant climb of the ride. This climb is a bit shorter than a mile and averages just under 7% grade overall but, coming as it does at the 20-mile mark of the ride, it might feel unwelcome in case you happen to be starting to get tired by this point. On the plus side, there isn't much that's uphill left for the rest of the ride after this, if you don't count a quarter-mile stretch right after South Park Drive.

You enter Tilden Park via South Park Drive. This paved road is a steep descent, as I've already explained, when done in this direction. It's over before you know it. It also happens to be closed to motorized traffic during "newt season" (from November 1st to March 31st). Motorized traffic will be a fairly constant accompaniment for the rest of your ride through Tilden, at least on weekends, because this is a pretty popular and heavily used park.

Once you reach Inspiration Point, solitude will be restored to your ride. The road after Inspiration Point is a curvy, gentle descent that's semi-deserted, fun, and in its higher parts, quite scenic. By the way, since Inspiration Point is a vista point with a fancy name, you might feel the urge to stop there to check out the views. It couldn't hurt to do that, but most of the scenery from there is toward the San Pablo Reservoir, and you should know that you'll get to catch much better views to both the San Pablo and the Briones reservoirs during your remaining descent after Inspiration Point anyway.

Once you're back on the valley floor at the end of the last descent, you only have an easy cruise left to take you back to where you started in Orinda. Parts of this segment on Camino Pablo is runway-wide, though a brief segment has a surprisingly narrow shoulder that feels intimidating due to the moderately heavy traffic of this road. (Refer to my Three Bears Loop ride description for more details on that narrow stretch and how it can be avoided.)

If you feel like extending this ride, you won't have difficulty in finding options. For extending it into a longer road ride, almost any country road you can wander through on the inland side of San Pablo Ridge would work. (I find the bay side of the ridge too urbanized for a good road ride.) One such popular option is one of the few "named" road rides of the East Bay, known as Three Bears Loop. To do that, you can simply take San Pablo Dam Road northwest instead of turning onto Camino Pablo toward the southeast near the end of this loop, and follow Castro Ranch Road, Alhambra Valley Road, and then take Bear Creek Road back to San Pablo Dam Road. If you happen to be doing the ride on a trail-capable bike, you also have a number of trail-based options you can use for extending this ride, because the route passes by the doorsteps of Lake Chabot Regional Park, Redwood Regional Park, Joaquin Miller Park, as well as Tilden Regional Park itself (not to mention Tilden's adjoining neighbor, Wildcat Canyon Regional Park).

© Ergin Guney


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