
This is a belated recap of a ride we led on May 19 but it’s also a reflection on the changes or lack thereof on this venerable set of roads. We led a ride on the Midpeninsula, a loop down Cañada Road through Woodside and onto the Portola Valley loop and then back via Foothill Expressway and Sand Hill Road and back. We’ve led a variation of this loop many times but they’ve all been longer. This time we cut out the hills in Los Altos Hills to shorten the route as well as reduce the elevation gain. Absolutely no one joined us, which is no great shakes since we intended to do this ride whether or not anyone from the club deigned to accompany us. (Carl wanted to attend but he couldn’t get a lift down the Peninsula and William had to back out at the last minute.) I’ve been doing this ride since I was a teenager and the enjoyment hasn’t diminished over the years. That’s partly because these roads have hardly changed at all in any significant way. Specifically, these areas have had very little “development” since the 1960s and so their charm has remained much the same.
The club has had rides down Cañada Road, Woodside, and Portola Valley since the early days. The club first went down there in August 1984 for a Bicycle Sunday. Early members of the club such as Derek Liecty, Ken Leeds, Bob Humason, Mike Reedy, Mark Reverdy, and I all led rides down there, some variation of Cañada Road, the Portola Loop, and the environs such as Stanford. As part of the 30th anniversary and then again for the 40th anniversary Roger and included it as part of the monthly ride series to commemorate special club rides.

The start is at the north end of Cañada Road where it ends at Highway 92. But that’s just because so many club members live in San Francisco. You could just as easily start at, say, Stanford Shopping Center or Woodside. Every Sunday is “Bicycle Sunday” and the road is closed to cars. Back in the day it was never closed off even after I-280 opened up and slurped up most of the north-south traffic. Before I-280 was open it was another matter: Cañada Road was a high speed arterial for commuters seeking to avoid getting stuck in the morass on 101. Believe it or not I-280 is fairly young—it was completed sometime in the early 1970s. I remember driving north on Cañada Road on the way to San Francisco looking at an empty I-280 still under construction. In that era traffic on Cañada Road could be quite dangerous because drivers were hellbent on getting to work and home. It was essentially an undivided two-lane freeway with cars racing by you at 60+ mph. The only thing holding drivers back was the occasional presence of the Highway Patrol or the county sheriff. The opening of I-280 was a godsend for commuters as well as for us relieved cyclists. With the opening of I-280 instead of being relegated to scurrying about Cañada Road only on weekends, we could scurry about during the week as well with less fear of being smashed.
Bicycle Sunday came about as a reaction of the traffic on Cañada in 1982. If I recall correctly, originally it was just once a month and then not at all in the winter. Some years later it became popular enough to warrant closure every Sunday. The original south closure point was Edgewood Drive, which is at the southern entrance to the Filoli estate. This closure produced a nice, long section that was swarmed with cyclists, walkers, runners, nordic skiers, and inline skaters. At some point Filoli must have objected because it wanted visitors to enter at its northern entrance instead and so the closure point was moved a mile further north. Still the shortened closure section is about four miles and is very popular.
Cañada is not flat, just flattish. It rolls—mostly gently—and each uphill although not long is sufficiently steep and long enough that you feel it in your legs. Often in the late morning or early afternoon the wind from the northwest picks up and so the return leg is more effortful. Incidentally Cañada Road is a great place to practice time trialing. It’s flat with smooth rollers, the traffic generally isn’t horrific, the shoulder is wide, and the sightlines are very good. Not being entirely flat means you also have to work on keeping your position going downhill and powering uphill but staying in a tuck. Needless to say that headwind is an incentive to stay in your tuck.
A mile or so from the start is the Pulgas Water Temple, a faux neoclassical structure that marks the terminus of the Hetch Hetchy Aqueduct bringing water from Hetch Hetchy in Yosemite to San Francisco. It’s seemingly in the middle of nowhere with no other buildings or structures visible anywhere nearby. There is a lot more vegetation now than when I was teenager. Back then it really stood out, a small Greek temple amidst the scrub brush and oaks. It’s also now surrounded by a stout fence and gate. When did that go up? It used to be completely open and high school kids could drive out there and have parties at all times of the day or night. Oh…that’s why it has fencing! It used to be that in the middle of the small temple was a downward portal where you could see a veritable flood of water pouring out of the underground pipe into Crystal Springs Reservoir. I recall the first time I visited it my high school buddy John Youden told me that previous generations of Paly High students would jump into the hole and get carried into Crystal Springs. It was impossible for us to do that, not just due to fear but because the portal even back then had a metal grate to prevent idiot kids from jumping in. In any case it would have been a long walk out and probably unavoidably through a shitpile of poison oak to boot. I understand that the bulk of the water no longer enters through the temple anyway, so it really is just a cosmetic artifact. Nonetheless it’s worth a visit and it’s also a place to get water—duh!—and use their convenient portapotties. By the way the grounds are much better kept these days than long ago. There is a reflecting pool, a manicured lawn, and wellkept foliage, almost too wellkept to fit in the near-wild and natural scenery of Crystal Springs. But it’s also a pleasant place to plunk down on the lawn and have a picnic or take a nap. You should know that the natural areas along Cañada Road contain serpentine rock and rattlesnakes. More than once I have seen rattlesnakes sunning in the road. Serpentine rock contains naturally occurring asbestos, which is a known carcinogen.

Otherwise Cañada has not changed much in the 55 or so years I’ve ridden it. The northern end is SF Water’s property, the Crystal Springs Reservoir, and then just below it are Filoli and the old Phleger estate, large private parcels. Filoli was made famous by the early 1980s TV series Dynasty. The Filoli mansion is shown in the opener during a flyover. The Filoli mansion masqueraded as the Carrington’s mansion and if you are a fan of the program, you’ll scream with delight when you see it in real life. Dynasty was not only a popular TV series, it was THE program to watch in the LGBT community mainly because of Joan Collins’s character Alexis Colby. Drag was never the same! In 1984 Ken Leeds, who later was a club president, led a ride down Cañada just to visit Filoli. The following year Jim King and John Digneo also led that ride and called it “Dynasty Revisited”!

Then you enter Woodside. The central part of Woodside, i.e. between Robert’s and Sand Hill, the residences are not cloistered together and the lots are probably two acres or more. For a suburb it feels awfully “semi-rural”. It’s like a time warp to some pre-tech, pre-YIMBY age. Except for the incredible congestion in Woodside proper especially on weekends: at Robert’s store you’re rudely made aware that you are at Ground Zero for growth as motorcyclists, automobile day trippers, and the Peninsula’s cycling masses collide at the four-way stop. Obviously Woodside isn’t interested in ruining their semi-rural lifestyle by installing a stop light, so everyone gets to do a do-si-do at the stop sign leading to honking horns, a lot of rudeness, as well as “no ma’am after you!”.
By the way when you enter Woodside along Cañada Road there are two stop signs. Cañada Road slopes downward towards the town center and over the years those two stop signs have engendered a culture war. In the 1960s and ‘70s there was so little cycling traffic on the road that we were an afterthought. Sometime in the 1980s apparently cycling picked up enough that local Woodside residents asked for enforcement. Compared to today the number of cyclists back then was still a trickle. On weekends there would be a Woodside cop parked on the side doling out tickets to cyclists who dared roll through the stop sign. I recall a club ride when one of us ran a stop sign and immediately the flashing red lights came on as a cop car pulled over and given a citation to the hapless rider. Fortunately I was behind so I was able to see this transpire and avoid getting cited. We soon learned to come to a complete stop. I’m not sure what enforcement is like these days when the number of cyclists peppering Cañada is like a non-stop parade. But on this particular day there weren’t any cops. (We stopped anyway!)
There are several ways to get to the Portola Valley loop from Woodside but the most direct is Mountain Home Road, which goes right past Robert’s. Cyclists moseying on Mountain Home probably piss off the residents. But on this day there really wasn’t much traffic at all except for other cyclists. Mountain Home is quiet, shaded, gently rolling—in other words a perfect road to enjoy on a bike. When I was a teenager someone pointed out Joan Baez’s home along there.
Portola Valley loop is probably the most ridden route in the Palo Alto/Stanford area, at least it was when I was living down there. Like Cañada and Woodside, little has changed in Portola Valley and it will remain that way even if the YIMBYs get ultraviolent. Like Woodside the average parcel size is big, one to two-and-a-half acres as the community was originally agricultural. In the 1970s we’d ride out to Portola Valley to buy strawberries from Webb Ranch’s farm stand next to I-280 and pick up manure for our garden. By the way Webb Ranch is still in business; the family must really like farming in Silicon Valley because just about everyone else has sold out and their farm is sitting on some of the most expensive real estate around. I’m not sure if it has made much of a difference for hindering growth but the town sits squarely on top of the San Andreas fault. The result is that PV is still a strange rural mecca in the middle of Silicon Valley and thus a favorite for cyclists. After passing through the “town” proper (i.e. the city hall area) the road ends at Alpine Road. Back in the day we’d turn right and head up Alpine to where it turned to dirt and ride up to Page Mill Road and Skyline. But dirt Alpine suffered a series of roadway failures in the 1980s and early 1990s and was abandoned by all but mountain bikers. Interestingly Alpine has just reopened after a major repair of the old dirt road so we can once again get up to Skyline without having to deal with cars.
The usual route is instead to turn left at Alpine and head towards Stanford. This is a long, steady descent that eventually meets Arastradero Road; if you continue down Alpine past Arastradero, you’ll pass under I-280 and eventually get to Junipero Serra Boulevard and then Sand Hill Road. At the intersection with Arastradero still stands the old Alpine Inn aka Rossotti’s or “Zott’s”. This roadside beer garden has been there “forever”, i.e. since 1852. Being so close to Stanford it was naturally a big hangout for students especially since Stanford used to be completely dry and Zott’s wasn’t too far to head to for a beer or two. The burgers there used to be really good. Perhaps they still are but each time I’ve ridden by it recently the crowds in front have been a deterrent; I like a mid-ride meal stop but I’m not sure I want to hang out for a half-hour waiting for it. I’ll have to bite the bullet some time soon and check it out. Zott’s used to be a big biker hangout too.
We almost always turn right onto Arastradero as we did today. Arastradero used to be a deserted back road, really a cut-through. Other than a couple of research centers associated with Stanford there wasn’t much there. But that’s all changed. Housing has encrouched from the Page Mill Road side and the Arastradero Preserve was created in the middle with a convenient parking lot and trailhead. The Preserve keeps that open space open and is a pleasant place to go for some easy mountain/gravel biking. But it also has brought more interest and hence traffic to Arastradero. The Arastradero Preserve parking lot has a nice place to stop for water, rest, and restrooms—not the usual pit toilets! (This is Palo Alto, mind you!)
Arastradero ends shortly to the east at Page Mill and now you’re really in the suburbs, ie. higher density and no more “semi-rural”. The only way to avoid that is to head up Page Mill for some miles until you’re back into open space. But that’s a big climb. So instead we did our usual, turned left and headed to the hillier part of Los Altos Hills along Purissima Road. Except this day we were cutting those hllls out and instead avoided Elena and headed back to the flatlands on La Paloma and Fremont Roads. Then you’re in Palo Alto in the tech campus area—VMware, SAP, Broadcom, PARC, Google. At least on weekends the traffic is very light. At this point you’ve lost the rural or semi-rural ambiance and are solidly back to civilization as we know it albeit with much better asphalt than you’ll find in most cities in California. Earlier we were where the rich and not-so-fabulous live and where they work, or at least feign to telecommute from. It’s funny how the Midpeninsula has changed. Back in the day the really rich were all in Atherton and Hillsborough. They’re still there but the nouveaux riches settled next door in Palo Alto, Woodside, PV, and Los Altos Hills with their ostentatious trophy homes and security perimeters. Even East Palo Alto, which used to be a low income neighborhood—I used to visit frequently because I had friends who lived there—the houses now lack metal bars on their windows and doors and they have Porsches in their driveways and solar panels on the roofs. Even one of the poorest neighborhoods in the Midpeninsula has been made solidly uptown. Palo Alto used to be so boringly middle class and now it’s some weird mashup of tech, money, and well, somnolence.
Then it’s back to Woodside along Junipero Serra. By the way Junipero Serra is the de facto bike “highway” in the area: if you want to get anywhere north or south, the fastest way is Junipero Serra/Foothill Expressway. It’s got very good shoulders/bike lanes and runs from Sand Hill all the way down to Cupertino. It’s much, much safer and less trafficked than El Camino and even though it’s closer to the hills it’s just slightly more rolling than cycling on the flatlands, enough to make it interesting and pleasant. Although everything has pretty much remained the same from Page Mill south, there were a few subtle changes from Page Mill north along the western edge of the Stanford campus. Now there is a short, paved bike path on the west side of the road, one of the few bike-specific changes although it’s hardly needed given the wide shoulder. Further north there are several median dividers where there used to be none at all; apparently as part of the bike lanes suddenly become separated from the vehicle lanes I’m presuming to ensure that cars don’t lean into the bike lane to avoid the median separators. JS/Foothill is another undivided two-laner with few stoplights and is quite popular for cars to speed on.
After making the convoluted turn to get onto Sand Hill it’s always a long slog up to I-280. Sand Hill was probably best known for being the home of SLAC, the Stanford Linear Accelerator. But it was also—to me at least—known as where Linus Pauling had his offices. It’s now a breeding ground of venture capital offices. Cycling up Sand Hill is never easy. It’s not steep but it’s steep enough! And it’s long enough that you have to keep enough fuel in the tank to make it to the top. Then there is a short descent to I-280 and things used to get very interesting because cars would be blasting down to quickly enter the I-280 ramps at the same time cyclists are trying to move left to continue west on Sand Hill. When I was younger you expected no mercy from the cars, so timing your move to the left was critical to staying alive. Then once you’re past that obstacle you had to contend with traffic coming off I-280 merging in from your right who, again, were exiting at high speed and giving hardly a thought to cyclists. Now it’s a little bit better: there is green paint on the road to warn cars that the bike lane is continuing across the entrance ramp zone.
Sand Hill then ramps up, a short but steep hill to the equestrian center at the top and then a very fast downhill to a right turn onto Whiskey Hill. You’d hardly know it but the western side of the Whiskey Hill has a series of giant estates. They’re all discreetly hidden behind trees and long driveways from the road. After college I briefly ended up painting houses and helped stain a gigantic all-redwood house off Whiskey Hill. The owner was a young guy high up in Eagle Computer Company in the 1970s. He’d made his fortune and it showed in the huge estate he now owned. Lovely. And yes, he had a Porsche. You remember Eagle Computer, right? Probably not. It was an early computer company during the “hobbyist” era and they went on to make IBM PC clones and had quite a name. Unfortunately the CEO died when he crashed his Ferrari just before their IPO and the company went into the graveyard with him. But I digress… That right turn off of Sand Hill is a mother: you’re going fast and have to take a quick right turn at speed to keep momentum to get as far up Whiskey Hill as you can. It’s better now but back in the day there was often gravel in that curve that tested your resolve. In high school I was riding with my buddies and one went down in the curve, just going too fast. Ouch. By the way, did you know that “Whiskey Hill” is the old name for Woodside? in the 19th century this was redwood logging territory and the Pioneer Saloon at the corner of Whiskey Hill and Woodside Road—still there!—was the “refreshment” center, hence the name.
Back in central Woodside we stopped at Robert’s to get a bite. Robert’s has been the town grocery since I was a kid but it’s a bit more uptown than it used to be. Back in the day the owner didn’t like cyclists, or at least he didn’t like cyclists trying to use his restrooms. He had a portapotty outside in the back installed for a while but it’s now gone. While there we ran into a club ride of classic bike enthusiasts. There was another old fart on the oldest Masi I’d ever seen. He didn’t know the exact year it was built but he said it was probably 1950s. It was so un-Masi-like—the lugs, the indented chainstays (!), and the decals. Another old dude was on a classic Peugeot. We had a nice chat as Masiphiles tend to do. Glad to see these “old” bikes can hold their own on the road!
After our snack we rolled north on Cañada back to the car. It’s afternoon so of course we had a steady headwind all the way back. Oh, and we stopped at the two stop signs too. Past the Pulgas Water Temple the wind picked up as did the grade and I slogged behind Roger trying to get as much wind break as possible. It was a beautiful day on the bike as always riding on the Midpeninsula.














