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Making a New Tradition with "The Longest Day"

Factor O2 VAM on a bridge near Pescadero, CA during The Longest Day adventure.

Traditions are for Bike Riding Too

Last year, I was frustrated with the way things were. I know we all were. 2020 was a hell of a year. So I opted to actually go for this whole “Longest Day” thing that has become quite popular in the cycling community. And I even did it solo. It was a big, big day for me, enough to the point where I wrote about it on this blog.

A lot of training, both physically and mentally goes into a ride like this. So when I was invited by a good friend from out of town to do it again this year within a smaller group setting, I was a bit unsure. Was I ready? I had literally just ridden the day before, and was on track for a 200 mile week if I went.

Whether you think you can or you think you can’t, you’re right

I wrote this last year when I reflected back on my ride back then. It still rings true today, so I got the nod of approval from the girlfriend and committed to my buddy.

Ride Details

Interestingly enough, a lot of this ride lined up with the ride I did last year for this same “event”, if one can call it that.

What made this one interesting

Despite me being pretty familiar with this area generally, there were a lot of roads through the mountains above Santa Cruz that I hadn’t really explored. At least not in person, nor on my bike.

So I got excited.

I almost blew up early

Turns out that the two guys I rode with this particular day are fast riders. At one point they were ripping through undulating terrain outside of Pescadero on Gazos Creek road, while I was pulling 350 watts (well over 4w/kg for me) just to keep up.

It was fast. It was incredible. And I also won’t forget that memory any time soon.

The Santa Cruz county line sign along Cabrillo highway near Davenport, CA

We even got up Old La Honda (our preferred route over the mountains of the peninsula) in about 24 1/2 minutes. And that was with my buddy “taking it easy” (his words, not mine). I remember thinking at the top of it that these guys better peter out soon, while I was also mentally telling myself to keep the long game in mind.

That meant that when we got to the rest stop at Whale City Bakery in Davenport, I made sure to take my time to recover a bit, and then proceeded to order a lot more food and beverages than I typically do. I wish I had more photos of it, but it was a mix of relatively easy to digest carbs and protein in the form of a ham and cheese croissant, a cookie, a coffee, and a coconut water. Recovery of champions!

A ham and cheese croissant that I ate at Whale City Bakerty

Bonny Doon and the Grade Roads

I loved this part. It’s so beautiful out there, and it’s been a while since I’ve ridden with other riders that were very confident on the downhills. Not to mention that some of these roads are pure bliss. I wish I had recorded some of it with my mounted GoPro! But alas, when doing a long ride like this with others, your mind tends to focus elsewhere.

Street sign near Felton and Empire Grade roads

Definitely some steep pitches on the way up, but it’s amazing to see how the terrain changes. On this particular day, we left the cloudy, chilly coastline and made our way up into the hills near Big Basin, filled with greenery and clear skies. It truly is marvelous to feel like you’re literally diving into the shaded trees at full throttle, g-forces leaning in and out of the turns.

Mountain Charlie, Bear Creek, and Skyline

The route took us up and around quite a bit more, up Mountain Charlie Road, around Bear Creek Road, and eventually finding our way back to Skyline. This is a LOT of climbing, let me tell you.

Mountain Charlie

I did this one last year, and have done it several times prior to that. It’s not easy, mainly because there are a few pitches that are well into the upper teen percentages, and a few beyond 20% I believe. On its own, it may not be that bad, depending on your personal experience and your affinity for climbing, but it almost always seems to be along the route during a truly epic day. Just means it’s a bigger challenge!

Factor O2 VAM bike with plaque about Mountain Charlie at the top of Mountain Charlie road

Bear Creek

The majority of this road we did wasn’t too steep, at least in the direction we did it. It was a marvelous, windy road that didn’t have too many cars along it and took us all the way back down into Boulder Creek, where we stopped for more water and snacks. It was at this point where fatigue was really starting to settle in for one of the guys, who eventually had to slow it back a bit to regroup with us at the end of the day.

Two bikes leaning against a store wall in Boulder Creek, CA.

Serious kudos to him for that effort, though. He definitely bonked, and it is one of the worst feelings to have while out on a big day. Recovering from that while also continuing to move forward and finish your ride requires a lot of mental fortitude and serious dedication. In the end, while we did finish separately, he was not that far behind, so chapeau to you, friend!


This was more of the finale for me, as the climb up to Skyline via the 9 highway is a steady, but extremely long uphill grind. The entrance to Big Basin, when it was open, was about half way up this, at the corner of where the 236 and the 9 meet, and it feels like you’re a hundred miles away from your usual riding grounds.

Luckily, there’s a viewpoint most of the way towards the top that allowed me to catch my breath a bit and try to mentally cope with the idea that I had just ticked over the 100 mile mark and was within 18 miles of my car in Woodside, most of which was, gasp, downhill!

Portrait of a Factor O2 VAM bike at the Sempervirens viewpoint

I actually started to have some muscle cramps in my legs at some point along Skyline, so I definitely took it easy when I was able to, and we stopped for a couple pictures along the way.

Factor O2 VAM bike at viewpoint along Skyline Drive in the Bay Area, California

If you’ve never experienced “Golden Hour”, when the sun is within its last hour or two of the day, along Skyline, you’re missing out. It is seriously magical, especially when it’s relatively warm and clear, like it was for us that day.

Close up portrait of local bushes along Skyline Boulevard looking west out over the ocean

Although as beautiful as all this was, I was so happy when we crossed past Alice’s Restaurant and I was back on very familiar turf, ripping down the 84 highway for a nice, smooth decent back to where I had parked my car.

Some General Thoughts on This Year’s Ride

As I think back on this whole adventure, there are a few things that I feel are worth mentioning.

Keep your nutrition in check

I’ve been lucky lately that my nutrition has not been something I’ve had to really actively manage. This is not always the case! Some people definitely have different gut biomes and often are not able to stomach certain kinds of energy-based food items that are marketed to cyclists or other active people.

On longer rides like this, staying on top of your game is a serious task, and it’s not one you can wait on. You must get it under control early and often. This means drinking more than you think you should, sometimes eating more than you think you should, and being very mentally aware of what you’re feeling compared to how you’ve recently been training.

In my case, I didn’t eat as much as I probably should have during the first 50 miles of this ride. I was lucky that I was able to digest as much as I did at the cafe stop, but that was me already pushing it. Again, I got lucky!


This is one that I think a lot of newer cyclists are initially scared of, and something that I think a lot of us who have been riding for a while may be a bit rusty with. At least given how 2020 went. This is crucial on larger, longer rides like this. Rotating who is in front regularly is a great way to essentially extend everyone’s distance that they’re able to do comfortably, as it significantly helps break up the efforts and power needed to go your current speed.

Learn the hand signals, be aware of your group, and take your turn on the front. I remember several times being a bit more tired than I wanted to be, so I found myself wanting to be selfish and hanging back a bit when the implication was that it was my turn. I remembered that I didn’t want to be that guy, so I reminded myself of the expectation. It’s an important one if you want to build camaraderie and if you want to be invited back by the same group next time!

Know the Route

Even if you don’t actually know the route itself, or it’s a new one to you, download the route into a bike computer and use it. Look at the route a day or two before, check out Google Maps, particularly street views, and even look up blogs and websites that cater to cyclists about specific climbs that you see along the way. There could be some really good tips there to help you out!

And loading the route into a bike computer, especially if you have one that shows an active elevation profile as you ride along a prescribed route, is super crucial when pacing out your efforts and mentally breaking up the ride into chunks. If you feel like you’re lost or don’t know how much longer “this stupid climb” is, your mind is likely to break, which will naturally make everything else start to fall apart as well.

Know your own limitations

Don’t be stupid. I mean, I think that goes without saying, but break it down into numbers if you have a power meter with you. Or at least try to quantify things in your own brain if you don’t. Think about what your typical FTP (Functional Threshold Power) is and be mindful of it. Understand that you won’t be able to hold that pace indefinitely. And scale back in your power zones, even going easier in some cases earlier into the ride than maybe what you’re used to, keeping the end goal in mind. You want to finish the day, not have to call it quits because you took too long after bonking to recover and didn’t pack a headlamp.

A New Tradition? Perhaps so!

Considering that I’ve never done a Rapha Festive 500, I’m kind of shocked that I’ve done this two years in a row now, if I am to be quite honest. It’s a great way to really kick off the summer here in the Bay Area, though. Besides it giving you an excuse to train for something, it’s also just a wonderful way to get out of your usual zone of riding into something a bit further away that maybe you’re not as used to doing.

It doesn’t have to be something as crazy as what I’ve done, not by any stretch of the imagination. And don’t let others pressure you into something you aren’t ready for, either.

But definitely strive for something big, your definition of big. And your definition of awesome. It’ll be an adventure!

Factor O2 VAM bike at the top of the 35 and 9 highways in the Bay Area, California
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