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Length 14 miles
Time 1 hour*
Total Climb 800 feet
Fun Rating
Scenic Rating
Aerobic Difficulty
Technical Difficulty 
* On a road bike

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The Loop (Stanford)
100% ROAD

It's probably a little presumptuous to name any ride "The Loop", but I've seen this route called that in a few written sources that are seemingly unrelated to each other, and that's been enough to convince me that this ride has truly earned this appellation among the riders in the vicinity of Stanford and Palo Alto. This is an easy and fairly short road ride and—other than navigating some nice and leafy suburbs and country roads—doesn't have any special feature that sets it apart from other rides, which makes me think that the celebrity implied by its nickname arises more from convenience than from any kind of superiority. The ride is situated where it could be an out-the-door ride for many bikers, including (perhaps crucially) people at Stanford University.

The starting point for the ride is subject to one's taste and convenience. The only definitive portion of this ride route is the loop that starts at the intersection of Sand Hill Road and Santa Cruz Avenue. How you get to that spot may vary. Those who live within riding range of the loop would obviously prefer to bike their way in from their own doorstep (including from the university campus) while those who will be driving in to ride here may opt to start from a spot further down Sand Hill Road where parking may be easier.

You'll notice that the ride route shown on this page starts from the parking lot of the Stanford Shopping Center. While I'm normally against parking in the lot of a business for a bike ride (unless I intend to become a customer of that business after a short ride), I don't feel too bad about bending that rule in the case of shopping malls. Like most shopping malls, the parking lot here rarely fills up completely, so parking in a remote corner of the lot typically won't be taking up space that other customers would need and depriving the shops from extra business. This is especially true because parking here by cyclists does not seem to have become something that is habitual enough to pose a problem for the mall, as far as I can tell. The only time the entire parking lot may be needed for the mall's customers is likely to be the weekends during the peak holiday shopping season, so you could avoid parking here during that time period if you really want to be conscientious about it. Keep in mind, though, that you'll probably attract too much attention if you park in this lot during a time of the day when there's no one else around (e.g., when the mall isn't open), in which case you might be shooed away by a mall attendant. It would, therefore, be good to have a Plan B for a parking location also in mind if your main intent is to park at the mall. Note, however, that most public parking on the Stanford University campus is metered, which may be an issue if you expect your ride to take longer than the time limit. Your next best option might be to look for a nearby residential neighborhood where street parking is legal.

The portion of this ride that's on the northeast of I-280 has significantly more traffic than the part that's on the southwest of I-280. In fact, if you happen to do the ride around the morning rush hour, the traffic on Sand Hill Road can be downright congested. (I haven't tried this ride during the evening rush hour, but that might be the same.) It's also worth noting that the ride passes through two freeway interchanges (both of them with I-280) where you have to ride in a bike lane that's in between traffic lanes as other vehicles try to merge in and out around you. If you're the kind of rider who feels uncomfortable riding in traffic, this might be an important point to consider. Once you cross I-280, however, traffic ceases to be a major factor. Meanwhile, there is ample shoulder space and bike lanes along the entire route.

The ride involves no serious climbs. There is a gentle elevation gain as you head away from the bay and a corresponding mild descent as you head back, but this is barely noticeable. You do need to put in some moderate effort as you get closer to I-280 on Sand Hill Road earlier on the ride, but the only two stretches that really feel like a climb arrive shortly after the first crossing of I-280. Only one of these uphill segments exceeds a grade of 6% and neither of them are sustained for very long.

There isn't too much in the way of points of interest on the ride. If you're not from the nearby area (or not involved in the tech industry), you might not know that Sand Hill Road is to high-tech venture capital firms as Wall Street is to investment banks or as Madison Avenue is to advertising agencies, which makes the name of this road a "metonym" (look it up). The ride takes you through the (very) well-to-do town of Portola Valley, which usually ranks as one of the top 10 in the US in terms of average household income. You may have heard that Portola Valley has a higher population of horses than of people. While that seems to have been true only in much earlier years, this is still a town with a very high rate of horse ownership and, just like in the neighboring Woodside, you shouldn't be surprised if you encounter residents heading to the corner store on horseback. The only other spot along the ride that I find worth a mention is Alpine Inn that's right on Alpine Road, near its intersection with Arastradero Road. Long-time residents of the area might be more likely to remember this place as "Rossotti's". Having opened over 150 years ago, it's one of the oldest businesses on the Peninsula. One source calls it the oldest one that's been continuously operated. It has a pretty colorful history too, with claims including the availability of alcohol during Prohibition years, the presence of a bordello back in the day, and in its more recent past being known as a scary biker hangout before it became a big Stanford student hangout. The clientele and the shady activities at Alpine Inn seem to have been sanitized by now, but not the interior decor, apparently. The place is well worth a rest stop, if not a lunch break.

The location of this ride affords a few options for extending your saddle time. If you're looking for more road riding, you can easily divert your ride up Old La Honda Road to Skyline Boulevard. You can then come down via Kings Mountain Road if you want to stay on paved roads or through Windy Hill Open Space if you'd like to add some trail time. Another paved option for extension is CaƱada Road, which you can reach from this ride's route by taking Whiskey Hill Road into Woodside. Those who'll be doing this ride on a mountain bike can also easily add the nearby Arastradero Preserve to their ride for some sweet singletrack, or the "trail" portion of Alpine Road known to local riders simply as "Dirt Alpine".

© Ergin Guney


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