9 Minute Read

The Longest Day of 2020

A truly epic challenge that took me from San Mateo to Santa Cruz and back. Image contains: redwood trees, empty road, filtered light.

The “fun” of long rides

This post may be a little less for those not as crazy as I am, and perhaps a bit more for those of us who are. With the longer days of summer upon us, those of us who really enjoy riding their bikes along epic routes see this as an opportunity to do something really unusual, something to wow their Strava crowd and family and friends.

Quick Aside about “The Longest Day”

The last few years, cycling groups and, in particular, Rapha, have been advocating getting out on your bike during the longest day of the year and doing something unique or special. They even have a webpage about it. The emphasis is on pushing yourself, camaraderie, and enjoying nature in some way or another.

Sun rising over mountain along Canada road near San Mateo, California

What I chose to do this past weekend

I’ve had my eye on doing the section of road south from Pescadero, CA, to Santa Cruz. I’ve driven this stretch of road before, but never have I biked it. I usually balk at the idea because of how difficult it is to just get to this loop from where I am. But then again, this IS the “longest day”, right?

Growing up in Southern California, I’ve always associated the coast with the quintessential beach life, cruising with the convertible top down, vitamin D raining down on me.

…except that this is definitely not the case up here! However, a certain sense of wonderment has overtaken me when it comes to exploring this somewhat uncharted coastline. At least by bicycle. I enjoy doing the ride from Pacifica southward into Half Moon Bay, so why not further south into Santa Cruz?

Santa Cruz county line road sign along road in front of mountains sloping into the ocean

How I prepared

This was a bit more tricky than per usual, given the COVID circumstances we are all currently in. I prepared much like I would normally for a long ride with things like:

  • A lot of snacks
  • Money in both cash and credit
  • Cell phone
  • Hand pump (I have the non-bluetooth version) and saddle bag with extra bike repair parts
  • Sunscreen (SunBum is my favorite)
  • Scouted out food and water stops along the way

But on this day, I decided to try to bring a few extra things with me.

Prior to this ride, I even opted to lather on a bunch of Amp PR Lotion, which is a sodium bicarbonate lotion that mixes into to your muscles to help offset the lactic acid that builds up naturally in your muscles during extended exercise. I’ve been using this stuff recently and it’s not too bad. A bit messy (it feels like you can’t easily wash it off your hands), but you put it on just before your sunscreen and you’re good to go. It feels a bit tingly and seems to help give you a little extra “oomph” throughout longer rides.

Cyclist with a lot of gear stuffed into back jersey pockets. Image may


My favorite set up, my Pas Normal Studios set up. It’s become quite a popular brand over in its home country of Denmark, and has extended its influence across Europe and in a few cycling hubs elsewhere (San Francisco being one of them). Pricey, but seriously fantastic gear. You can be in this stuff for hours and not really “notice” your clothing like you might with other brands.

I guess that depends on your physique to an extent, though! They definitely skew towards the slimmer rider. I wore a few items mainly from their Mechanism line, along with a stow away vest and some thin arm warmers (that I find oddly warm) from Velocio that just so happen to match the blue bib shorts I own. Because of course they do.

Photo by PAS NORMAL STUDIOS in VĂ©lez de Benaudalla, Spain. Image may contain: one or more people, people standing, tree, sky, bicycle, outdoor and nature, text that says 'Mechanism Mechanism'.


I did my best to predict the conditions before this day, using an app on my phone called EpicRideWeather that is seriously worth the $9 a year they charge. I routed things out as I usually do with Google maps, then built a route in RideWithGPS, and then imported it over to EpicRideWeather. I gave it my start time, my expected average speed, and it showed me a nice detailed output as to wind direction and temperature changes expected throughout the day, based on where I would be at the time. Pretty rad!

Except that the weather wasn’t quite as I expected

The first part of the ride was wonderful. Filtered light through redwood groves out near Pescadero, going up the idyllic Old La Honda road, even meeting a fellow cyclist who was doing an “Everesting” attempt (I thought I was supposed to be the crazy one!). When I got out to the coast, however, the wind shifted and I was staring down into a headwind for basically 30 miles. Brutal.

Listen to that wind. Super fun, let me tell you.

To make matters worse, when I finally got up and over back into the Valley, the weather in Los Gatos hit 100 degrees! I was previously riding into headwinds, covered in misty clouds along the coastline, and it was 49 degrees. Luckily my kit helped insulate me from the elements, and I tried to just think about my goal rather than the frustration or discomfort that had started to settle in.

Back to what makes this “fun” for me

I was always a semi-athletic kid growing up, but never really did anything truly tough, sports-wise. I was never able to truly understand what made someone run or work out so hard they wanted to hurl. I also never quite understood firsthand the victory of accomplishing something that was truly difficult for me. Since I’ve found enjoyment in cycling these past few years, I’ve finally come to a mutual understanding within myself what it really means to accomplish something very physically demanding.

Building up to this

First of all, it’s not like I just straight up woke up one day and thought to do this. Perhaps I could have suffered through that, but I also could have hurt myself in doing so. Some people seem to pull this off, but I feel like that’s a recipe for disaster in most cases. These kinds of things take time and dedication, learning about yourself, and paying attention to how you feel as time goes on.

And that last part is particularly important. It’s one of the main reasons I like doing these distance rides.

Nutrition is indeed a science

I certainly cannot consider myself an expert in this category, but I have spent enough time trying out various snacks and supplements to get an idea of what works for me. I don’t usually have issues with my stomach handling too much sugar, for example, so things like Gatorade and other sugary drinks are not as problematic for me to get fuel from as it may be for others.

Things certainly do change on the longer rides, however. At some point during my ride this past weekend, I felt like I just couldn’t get enough carbohydrates into my system or enough water. And unfortunately by that time, it’s almost too late to get it even if you try, anyway. Your body is just too tired and there’s too much exhaustion. So instead you either bonk or suffer through the rest of your ride at half your usual power and a very low heart rate.

90% of these kinds of rides is mental

While this ride pales in comparison to other truly long-distance events like the Paris-Brest-Paris ride, I feel like I can speak somewhat to this point.

“Whether you think you can, or you think you can’t–you’re right.”

-Henry Ford

It’s absolutely true.

Once you let negative thoughts get into your head, you start to lose it. “I can’t keep going on like this”, or “This is terrible, I hate this” will all cause you to lose track of time, forget to drink water or eat food, make dumb mistakes, and basically just make a day that was filled with excitement into dread and horror. Each turn of the pedals will make you think about the pain you’re feeling and you’ll find yourself starting to fixate on all the wrong things.

Instead, I like to stay focused on the positive. The colors in the trees, the blue sky, the fresh air. Think about all the preparation that you’ve done, both in material and in your physical training, and have confidence in your past decision making that has lead you to this point. Then follow through with your plans while remaining flexible to potential changes if needed.

I know for this ride, I looked forward to the wonderful redwoods of the Santa Cruz mountains, the absolutely amazing descent down the Old Santa Cruz Highway, and the feeling of incredible accomplishment of knowing that I did a 200km-plus-some ride solo.

I actually wrote more about this very topic. A lot of this mentality can be attributed to Nietzsche, believe it or not.

The exhilaration of it all

Some of that stuff above sounds dreadful, doesn’t it?

In the end, it’s not as bad as you think. It never is. And I personally find that pushing yourself physiologically like this helps train your mental aptitude and fortitude elsewhere in your life.

Yes, it’s exhausting. Yes, it’s grueling and not fun at times. But at the end of the day, you can look back on something truly special. A wonderful experience that you got to see first-hand that others rarely do or can.

You made it an incredible distance on your own power.

You got to see sights and roads that others rarely notice, let alone appreciate.

And to top it all off, you likely learned something about yourself.

Bicycle posed against brick road marker for Mountain Charlie Road in the Santa Cruz mountains
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