Last year, I biked 100 miles to get to Big Game (Stanford vs Berkeley), and it was quite the adventure despite the cramping, rain, and extensive water damage to my phone and laptop (i.e. my livelihood). Although this year's iteration was on home turf, I was tempted to continue the tradition, and when a colleague suggested biking the other way around the Bay (on the east side), my fate was sealed: I couldn't NOT do it anymore——a ~100 mile route was staring me in the face.

So I charted a course: I'd bike from my office in SF, across the Golden Gate Bridge, through Marin, across the Richmond Bridge to Berkeley, down the East Bay to Milpitas, and finally up the peninsula to Palo Alto.

My conditioning wasn't quite as good as when I did my first century, but I figured that with a notch already on my belt, I'd learn from my past experience and the ride would surely proceed more smoothly. Right? Right?

In the wee morning hours (around 1:00 AM), I played a round of office Spikeball with my colleague, charged up all my devices, and bid him adieu. He worriedly asked me if I'd get drowsy biking through the night; I scoffed——what, am I going to fall asleep while pedaling? (That's called foreshadowing).

And then I was off! SF has a rather underwhelming nightlife, so the streets were completely deserted, the serene silence broken only by the buzz of overhead street lights and punctuated occasionally by the pedestrian crossing sounds. I started down Market Street toward the Ferry Building and biked the length of the Embarcadero toward Fisherman's Wharf:

I was already feeling slightly chilly, but given I'd be biking (i.e. generating heat), I wasn't too concerned. But then as I passed by the northern waterfront, it hit me.

It. Was. Cold. The temperature was around 47 degrees Fahrenheit, and with the cold air from the Bay blowing inland, it felt freezing. I was woefully underprepared: shorts, a long sleeve shirt, and (crucially) NO GLOVES. No less than 30 minutes in, my hands were numb.

But there was no turning back. The journey had started, and the only way to end it was to finish it.

I went to my favorite lookout point in the city:

Then across the Marina and a brief detour to the best spot in the city:

The Palace of Fine Arts is a truly spectacular place at night. Softly glowing lights, the faint sound of water, and a spectacular architectural work.

The rest of the night would not be so pretty.

I kept biking along Mason Street over to the Golden Gate welcome center (it was so cold I had to alternate putting one hand under my armpit to warm it up) then climbed the hill up to the bridge. (There was a gate blocking the pedestrian walkway of the Golden Gate Bridge; to pass through, I had to press a buzzer and explain to some government employee why I wanted to go across).

Apparently my reason was acceptable (and sufficiently derisked any possibility of suicide) and I made it onto the bridge:

After you cross the bridge via bike, you're essentially deposited onto the highway and all its six lane glory. Although I'd biked it before and there were now fewer vehicles, it was a different animal in the dead of night. For whatever reason, biking at night is uniquely unnerving, significantly moreso than running.

I whizzed through the downhill toward Sausalito and was greeted by a spectacular view of the Bay:

And continued on toward Tiburon. At this point, my hands were in a pitiful state: squeezing the brakes took far more conscious effort than normal, and switching gears required me moving my arms so that my immobile thumbs would press the shifters. And I was dreading crossing the 5.5 mile Richmond Bridge fully exposed to the cold water air not far below.

Regardless, Tiburon and the Paradise Loop were stunning:

In retrospect, the picture doesn't look all that great; perhaps the thrill and the fear heighten the senses, or at least sharpen aesthetic appreciation. And that's really the point of escapades like this one: to see, to think, to feel, and to marvel at what the world (man-made and natural) has to offer as well as the capability of the human body to appreciate it.

I inched my way through Marin and made it to the approach of the Richmond Bridge——another harrowing experience as I snaked my way across the highway with cars roaring past and overhead. The bridge was surprisingly pleasant, offering a far more majestic view than the last time I'd crossed it (which was during a hailstorm).

After conquering the bridge, I worked my way through Richmond, hand temperature still asymptotically approaching that of the frigid surrounding air, and I was desperate for a brief respite at Berkeley.

The views were still nice though:

By the time I reached Berkeley, it was around 4:30 AM, and (essentially) the only open spot was a dejected Taco Bell joint, so I climbed a short hill, parked my bike, locked it (crucial in this primitive place), headed inside, and ordered a burrito. My hands were so thoroughly frozen that I physically could not double click my iPhone's power button to pay and needed to ask the cashier to do that for me...

I intended to take refuge in the Taco Bell for a bit and breathe some life into my hands, but for some reason they closed from 5 AM to 8 AM, so I was kicked to the curb.

And then I hatched a diabolical plan. The night before (i.e. 7 hours earlier), I was at my Berkeley friends' Thanksgiving potluck; if they neglected to lock the door (which would be truly remiss in Berkeley), then perhaps I could scrounge some leftovers, recharge my phone, and restore my body temperature. I biked over to the apartment, praying under my breath, and much to my delight found the door unlocked! After locking my bike (I wouldn't make their mistake), I crept inside and found a feast awaiting me——sushi, noodles, roast duck (that I had brought), Crumbl cookies, you name it——and I took advantage (I thought it was rather fitting to steal from Cal on the eve of Big Game).

After running my hands under hot water, charging my headlight, and sending a photo to my gracious (unconsenting) hosts, I was on my way once more.

With the cold predicament somewhat alleviated, a new problem cropped up. It was now around 5:30 AM, and I'd been awake for the past 20ish consecutive hours (and on top of that had only slept around five hours the night before). As I biked through Oakland (yes Oakland of all places), my eyelids grew heavy. I'd previously scoffed at the notion that drowsiness would stand in my way, but I quickly realized that you can indeed succumb to sleep while biking. First came the hallucinations (I saw animals and people where there certainly shouldn't have been), then came the real problem: as I was biking, I'd drift off to sleep, stop pedaling, and get jolted awake by my bike tilting to the side.

Despite my best attempts at staying alert (drinking water, eating snacks, intermittently walking my bike), it kept happening; I felt like Mr. Bean in that scene trying not to fall asleep while driving:

I considered finding a nearby bed and breakfast to snooze in for a few hours——but if I did, there was a good chance I wouldn't wake up. So this was how the journey would end.

Or was it? Sunrise was in just a few hours, and surely seeing the sun would reset my circadian rhythm, right? So I forged forward, teetering on the edge of consciousness (I truly have spectacular decision making capabilities don't I).

I saw more nice views, but in my barely-lucid state took few photos:

And after what felt like an eternity fending off sleep, the sun crept over the horizon, and boy never did I think I'd be so happy to see the sun.

Newly rejuvenated by the sun (though only slightly), I kept making my way down the East Bay. It was quite a spectacular sight as the sun rose.

At some point, I wanted to eat a snack (a That's It fruit bar, specifically), but my hands were so clumsy I wasn't able to open the package! I resorted to stopping an old Vietnamese couple walking along the trail and explained to them I needed help opening the bar as my hands were too cold. The man clasped my hands, said "oh shit" and then pulled out a pocket knife to open the bar. Bless!

But my problems had only just begun. A few miles later in Fremont, I found myself with a flat tire. Good thing I'd come prepared, I told myself——I had brought a pump, patch kit, and even a spare inner tube.

I stopped by the side of the road, flipped my bike over, and got to work——but there was something crucial to changing a tire I'd forgotten about: functioning hands.

I spent over half an hour fighting my bike trying to pry the tire off its rim with my floppy hands. At one point a kind woman stopped by and called her husband to see if he'd be willing to help, but he said it was too cold and he didn't want to get out of bed. Later on a troupe of bikers zoomed right past——bystander effect at its finest.

After I finally managed to wrestle my tire off its rim, I realized there was simply no chance I could place the new tire on myself——taking the tire off is an order of magnitude easier. So THIS was how the journey would end.

No! I'd already biked 60 miles and hadn't come this far and fought this hard to just give up. With all the time I'd spent trying to get the tire off and find the puncture, business hours were approaching, so I ran to catch a bus to the nearest bike shop and waited outside for a good hour or so until it opened.

After twiddling my thumbs for a while, the place finally opened and I got my tire replaced (turns out this bike's tire was extremely tight, and even with tire levers it took the store some time to get the fixed one on).

Finally, I was back to pedaling, and the rest of the trip proceeded without further hiccups.

It was, however, mind-numbingly boring. The East Bay has nothing. Endless grass and marsh punctuated only by ugly tech complexes of this-or-that multibillion dollar tech company. The East Bay could have been a futuristic metropolis like Shenzhen; instead it's just... nothingness and depression.

The final stretches of any long journey are painful, at least mentally. I was desperate to be finished, to return to the dorm and crash, and I had already done 80%+ of the work. But 20% of a lot is still a lot, and as I kept pedaling the mileage felt like it was moving at a snail's pace. But all painful things must come to an end eventually, and after 9.5 hours of moving time, I finally made it back to Stanford campus.

Though the bike ride was finally over, the aftereffects of it were not. The next morning, I woke up with my hands tingling, trembling, and weakened——I couldn't snap, play guitar, or even open a water bottle. But Claude told me the symptoms would pass, and they did, though it took a month.