Last Updated on 18 September 2026:
Cycling Route 66 had been a dream of mine since my father and I first talked about driving America’s most legendary road. Years later, after rebuilding my life through some very difficult times, I stood at Santa Monica Pier ready to attempt a 2,500-mile ride across the United States.
For me, life has always had a funny way of kicking me in the genitals, and then rubbing them better. I apologise for the crude metaphor, but I also feel that most people currently suffering will read this and relate, possibly to the latter part, definitely the former. Just noting that, if you’ve recently suffered the kicking part, it does get better…
I’m rewriting this blog (for Google purposes) three years later and I can tell you I’ve had a few more kicks, but reading this, reminiscing of good times, I can tell you, everything works out when you do the work.
Peace and love, brothers and sisters, I hope you enjoy reading my cycling Route 66 journey as much as I did riding it.
Dedicating this to my support team, who not only got me as far as I did, but continue to support me to this very day. Thank you, Chris, Thomas, Luis, and Alan – the real heroes of this story.
Cycling Route 66: Introduction
I remember fantasising when I was younger about driving the legendary Route 66. My father and I discussed taking a tour of it in great depth, but it wasn’t until I was thirty that it started to become a reality, albeit now cycling Route 66 instead.
When I was at my lowest, I was admitted to a mental hospital, an alcoholic, and an addict. I was told by many doctors that I’d be unable to function in normal society without a cocktail of mood stabilising drugs, and that I’d wander this planet in a constant tranquilised haze of irregularity.
Yet, at thirty years old, I was standing next to the ‘End of Route 66’ sign on Santa Monica pier with one of my best mates, Damen, chatting about my transformation. At that time, I owned and operated an international coaching business serving clients in over twenty countries, having won multiple awards in cycling, and doing all so managing the symptoms from my Bipolar Disorder unmedicated.
Having witnessed my life changes, Damen was adamant I share my story to inspire people as much as I did him. Back in 2016, it was easier said than done to share one’s troubles with mental health, something that is more frequent just five years later, but after some convincing, I agreed to do it, if I could tie it in with something huge. The idea of cycling Route 66 was born…
Cycling Route 66: Stage One
Flash forward two years and, again, I find myself standing besides that sign. However, this time it was 4:45 in the morning and I was wearing my cycling gear and preparing to start cycling Route 66. I had Thomas & Chris, my now good friends, there with me as I was about to embark on a 2500-mile journey across the United States. A terrible night sleep in a dodgy motel wasn’t going to deter me, nor was the thought of battling Los Angeles traffic on Labor Day weekend. I was ready, excited, and motivated.
Stage One was the longest stage with some of the hardest riding you can do on a road bike, a tough introduction to cycling Route 66. At over 240 miles, a mix between concrete jungle and desolate desert, I knew it was going to be a long day. The LA traffic never turned up and we took scenic rides through Hollywood and Beverly Hills. As we headed out of the greater Los Angeles area, which took us four hours, and into San Bernadino, the temperature was already warming up.
As with cycling in urban America, cycling Route 66 was an interrupted ride. Stop signs, traffic lights and cycle paths do not make for a fast ride. This took a heavy toll on my mood, knowing that we would be behind schedule that early on. Each day, the schedule included a two-hour cushion, which was to be used for breaks and other incidents. In the event I fell behind, the stops could be shortened to bridge that gap. It meant the only way to keep on track on day one was to be very efficient with time off the bike.
If you followed my training journey, you’ll know that I don’t really like gravel. During the first stage of the Haute Route Rockies, I took a big fall on the first stretch of gravel. I needed stitches in my arm and many trips to the medical team to get my wounds cleaned. While I am open to conquering my gravel fear, I didn’t expect there to be a half mile stretch of road work that left me riding gravel {sand}, with me slipping around as much as I was swearing.
Much of Route 66 has been replaced by the interstate highway system and, on the climb to Victorville, you have to leave the comfort of the frontage road and get on I-15 (“why am I not cycling Route 66?”). If you’ve never ridden a road like this, imagine a five lane highway with traffic moving at over 60 mph. The shoulder of I-15 was also a bombsite; you could probably build a replica vehicle with the debris left at the side of the road. Thankfully, I had Chris & Thomas in the car behind us with flashing lights and signage to warn other road users and we made the long trip up the mountain with me needing little more than a change of bib-shorts.
Once you finish any climb, you have, what you hope is, a pleasant downhill. Sadly, this is where the great state of California let us down. The frontage roads are very worn with large gaps, rough roads, and a ride more akin to the pave in Belgium. During my research for this ride, many of the riders that had ridden Route 66 had commented that they thought about, or did, jump the fence and ride I-15 for the better surface. I didn’t opt for this. I had a route to follow and I had to follow it unless there was a significant reason to deviate.
Despite being provided with, arguably, the world’s most comfortable bike, a Trek Domane, courtesy of William Sawyer Cars. I still took damage to all the points where my body made contact with the bike. For the remainder of the event, I would be riding with both sore feet, hands, and under-carriage (that region!). Although my feet did make a recovery after a few days, there simply is no preparation you can do for this. You couldn’t ride a mountain bike or anything setup like that, you’d be too slow and there’s no swapping of bikes unless there’s a serious malfunction of the bike. I was already riding 32 tyres, it was brutal!
We had a solid finish to this day as we made it into the Mojave Desert, with the heat not really letting up all day. We were eventually joined by Luis & Alan, who had picked up ‘The Meg’, the RV loaned to us by Road Shark RV. ‘The Meg’ was fantastic to have somewhere to rest each night and the sight of her each day at stops really motivated me, I can’t thank Ed and Johnny enough. We all rode into Amboy, a ghost town in the middle of nowhere, together in the pitch black.
Stage Two
Up at 4:15am to be on the bike cycling Route 66 by 5am. I didn’t feel too bad. Again, sleep alluded me, but from there on, every night I’d sleep with ease. The first obstacle of the day was the 10 or so California bridges that were closed. We were faced with the choice of a long detour, and ride on the Interstate, or to try to force a way around them. I had no doubt that, given it was bone dry, I could walk around the bridges if I had to. We also knew that the car could double back and drive around if it came to that, so the decision to push on made sense.
The bridges were certainly closed to cars, but after some thought and manoeuvring we realised we could simply drive the car around too. Simple, so we thought, but the final bridge wasn’t even there. It had gone, with no way to ride it. Like I had planned, I walked around. The loose, rocky surface was not easy to walk on and about half way around I twisted my ankle. I didn’t feel any immediate pain, but I was quietly anxious to see if this would come back to haunt me.
After a more relaxing ride on the Interstate, now I-40 which we would follow in some form for most of the trip, we crossed the Colorado River. That was a sight to behold; an amazing beauty set around such a barren landscape. We then headed deep into the Arizona desert where the temperature would be at its brutal highs in the 40’s (with my Wahoo topping out at 50c). This was the day I was thankful for my Spruzza the most, a small mister unit that sprays water into your face. With barely any appetite, I was drinking nearly 1.5 litres of fluids every hour and still suffering. I wasn’t able to enjoy the small town of Oatman as much as I’d have liked. This tourist town with its stray donkeys might be the only place on Route 66 where tourism is affluent enough to keep businesses going.
Thankfully, as we headed back towards the Interstate, the heavens opened and I was cooled by the rain. This was a welcome gift, bringing me back to a somewhat human condition. We stopped in Kingman for some food before Thomas & I headed back out to finish the last 75 miles. 240 miles done today and another late night, but still feeling surprisingly good.
Stage Three
We started and finished cycling Route 66in Arizona today. After yesterday’s predominantly desert day, it was nice to experience some of what the state has to offer at altitude. The first challenge today was major road work as we approached Flagstaff. Interstate 40 is not the busiest of roads, certainly nothing compared to Stage One’s Interstate 15! It is mainly a route for long distance truckers, many of whom gave a supportive honk of their horns as they passed. We imagined that in the time we were following I-40, we probably saw the same trucker many times. Anyway, everyone seemed nice and content to give me as much room as they could.
Unfortunately, the road work reduced I-40’s normal three lanes to just one. This meant the truckers had no option but to pass by me close. Again, I have nothing but massive respect for the guys and girls who drive long distances. In the vast majority they all were courteous and moved lanes to give me room on the interstate shoulder. In this instance they just couldn’t do that. To make matters worse, for short periods, the wide shoulder was reduced to no more than a foot. Having huge trucks pass you, well within the three-feet law (no fault of the drivers’), was terrifying. I mentioned to Chris, who could no longer drive directly behind me to warn drivers of my presence, that if it got worse, I’d quit the record attempt for my own safety.
Thankfully, it didn’t last forever. Thomas then joined me and we managed to ride down the newly paved closed section, having the whole side of the interstate to ourselves – narrowly missing a cop as we pulled off to ride the frontage roads once again.
After a quick mechanical stop to bleed my front brake, we left Flagstaff and headed towards the New Mexico border. With the wind with us we were flying, but the shoulder of I-40 was a really bad place to be riding something as fragile as a bike tyre. Thomas had three punctures, which shortly followed by me blowing a tubeless tyre wide open too. I was riding a set of the excellent Zed Bike Wheels, they rode well and you can tell a lot of care goes into the hand building of each set.
After spending a solid 160 miles on the interstate, I was glad when we pulled off and headed towards Petrified National Forest Park. After leaving I-40 we were on old Route 66. This was what I was hoping to see, old single track bridges and more reminiscence of what The Mother Road was like before the interstate programme was started. You can really feel the soul of the road here. All the pictures I had seen researching the trip, everything that filled me with joy and excitement was now right here in front of me.
As darkness approached, we were heading into the National Park. Here we encountered one of the failings in my planning. I hadn’t thought about park closure times and when we got to the gate it was shut. We could’ve {should’ve} jumped it and ridden on, but we would need to clear the park, nearly 30 miles, unsupported. This left us wondering if that was a risk too far. At worst, if we suffered a fatal mechanical accident, we would have to walk 15 miles in freezing conditions in the depths of the park.
With that in mind, we called it a night and parked up. It was during this stage my ankle had started to give me some issues, and when Thomas, our sports therapist, treated it I could tell he thought it was bad news. His face had a look of game over.
Stage Four
After losing over an hour in the schedule the night before, we lost another hour to the park opening in the morning. Rather than our usual 5am start, we jumped the gate at 6am and headed off, knowing that the car would be able to come through with us at 7am. This already put us around 50 miles down on our target, something that was hard to take given we had only ridden for three days.
Petrified National Forest Park might be the most beautiful area I’ve ever cycled in; made even more so by the sun coming up at dawn. I was lucky to share the ride with Alan, who I had met at Haute Route Asheville. Eventually we made it back to I-40, which we followed for around 70 miles, some on the shoulder and some on frontage roads. We even made a small navigational error upon approaching New Mexico and had to run across the interstate to get back on track.
New Mexico was a place I was excited to see. I’ve never been to this state and the thought of seeing some of the extra-terrestrial heritage along the route picked me up. Gallup was our stop for lunch, a nice little city, where I was glad to see ‘The Meg’ for a brief break.
I prepared a lot of my food beforehand. I mass cooked my favourite bars; a mixture of oats, seeds, dried fruit & 100% dark chocolate, there is nothing but goodness in them. I then vacuum seal them for freshness and I would eat about 5 squares a day. On top of that, we had a mix of bananas and other fruit, jerky, sweets, sandwiches, and gluten/dairy free treats, as I’m intolerant. My hydration was provided by Precision Hydration, who have tailored electrolyte strengths for my level of sweating, that is volume of sodium lost.
After lunch I was delighted to be heading away from the interstate. My delight was short-lived when the heavens opened and I got drenched. Now riding solo, I had no option but to push harder as, even wearing multiple layers, there was a real risk of hypothermia if I rode too slow.
My Stages power meter had been intermittently working for a few days and now the readings were nothing short of hilarious, setting a fictional 60-minute power PB during Stage Three. Ultra-endurance cyclists develop a good sense of riding to feel, but having power data to hold me back is beneficial. Stages were very kind in replacing my power meter post-event, even though it is outside of warranty.
Thankfully, the thunderstorm didn’t last forever and as soon as it dried up I was joined by good friend, Luis, for a stunning ride through the El Malpais Wilderness Area. Our finish, in Grants, was again behind schedule and we were unable to make up the distance lost the day before due to the hour late start in the morning and a further hour lost to time zones. Arizona doesn’t have daylight saving, so it meant we actually lost that time entering New Mexico.
Being behind and having to rebook RV parking was frustrating. Not only that, but this was a day where I rode slightly under a double century, two days in a row now and I hadn’t planned for even one day less than 200. With us entering Texas tomorrow, we would lose yet another hour to time zone changes.
Stage Five
I had figured out that if I didn’t flex my ankle I was able to stop it hurting as much. With the help of some k-tape and pain killers I was able to keep pedalling, even if this might be somewhat reckless.
Today was an incredible stage and I look back at this as one of my favourites, although Albuquerque was massively underwhelming {where was Walter White?}. There’s nothing that bad about the city, it just seemed to lack character and anything of great interest. Thomas even asked me when I thought we would be heading through the downtown area, I replied “a few miles ago”! It was an understandable question; I only knew because of the street signs counting back up.
The ride north to Santa Fe was simply incredible. Passing through the small town of Madrid, where the movie ‘Wild Hogs’ was filmed, was amazing. You can almost feel the alien energy, probably in part thanks to warning signs with little flying saucers above cows. Luis had joined Thomas and I and it was perfect weather. The climbing was stunning and it was fast descending, truly an amazing day cycling Route 66.
The main issue we found with us following ‘Bicycle Route 66’, designed by Adventure Cycling Association, is that it does take you on all the tourist areas, even off the main route itself. I had opted to use this route for continuity, so the next person had a route that wasn’t designed by me, something which could lead to bias. However, it did mean taking odd trips to historic landmarks, just for the tourist value in it.
Catching up today was going to be hard. The planned stage was already 230 miles, and we had now fallen around 50 down. Finding new places to park the RV overnight was hard. Sure, we can dry camp at the side of the road or at a truck stop, but then you have five people trying to use one bathroom. You also need to empty tanks and top up water/propane. You can get away with one night on the side of the road, but too many and you need to stop the next day during the ride to fill/empty these tanks.
The end of the day brought us to a stunning camp. Once you stray away from the busy roads there are so many smaller places full of character and history. Into Las Vegas (NM) for the night. New Mexico didn’t pull any punches in showing us how beautiful the scenery can be. Viva Las New Mexico Vegas.
Stage Six
As this was one of the least hiller days, I should’ve been able to catch up some miles, and after 45 miles of tailwind through the countryside we got back on the I-40, which we would follow for another 200 miles to finish the day.
If you want evidence of just how damaging the interstate programme is to Route 66, visit some of the towns along this section. They are empty wastelands. Every town is hopeful of one thing, tourists, but with far too much supply and nearly not enough demand, the towns along the route are all dying. In the years before I-40, these towns would have been prosperous places where weary travellers could rest their heads and find some food. Now they are desolate and devoid of any money, and barely surviving.
Once you descend from the Rockies, you will normally have a tail wind all the way to Chicago. Named ‘The Westerly’s’, it’s only about one in every five years that it blows in the opposite direction. Thanks to the hurricane about to make landfall on the east coast, this year would be that one in five, and I was faced with 200 miles of headwind today, with the prospect of over 1000 miles of headwind to come in the following stages.
To me, this was simply soul destroying. I’m sure we all hate wind, but it was never going to be enough to make me quit. When we were on the frontage roads, the grippy surface and lack of vehicles made me wish I could get on the interstate. When I was on the interstate, I was unable to switch off for even a second, with the danger of hitting debris or the rumble strip.
The road surface was almost as bad today as it was on Stage One. Some of the roads during this trip went on as far as the eye could see. Sometimes this was ok, others, like today, were just hard packed chip surfaces. I was delighted to turn off one of these roads at one point, only to be thoroughly disappointed to find a gravel section lasting around five miles to follow.
New Mexico has a high clay content in its river beds which turns a lot of its rivers red. While pretty and nice to look at, when faced with riding through it I had my concerns. One flooded section of the road I sent the chase car ahead to test the water and find a safe line. I could see by the movement of the car it was bad. I opted to run around the edge. While I didn’t fall in, it did take a good five minutes to clear the clay from my cleats.
I was very much looking forward to visiting Texas, another state I’d never visited. The border town of Glenrio would be a welcome stop for the afternoon. I was looking forward to enjoying a late afternoon break before the final push. However, taken in by entering a new state, I missed the off ramp. No matter, I thought, unlike the dual carriageways in the UK, where you can be on them for many miles before getting off, US roads typically have exits much more frequently. Ten miles later we pulled off at a rest stop.
We finished the day just outside Amarillo, one of the larger cities on the route. Now 70 miles behind schedule, we were facing the prospect of needing to use an extra day to finish the attempt. That was ok, no one has ever cycled Route 66 in the manner I was. The closest before was a woman who did it in 23 days. There was a Route 66 bike race one year, cancelled after multiple riders were hit by cars in Chicago. Many of the unaffected riders continued, but they were in groups. The only limit on our time was the support team needing to get back to their day jobs. It wasn’t what I wanted, but having to ride an extra day was looking more likely with every stage.
Stage Seven
This was the stage I was looking forward to most. The profile looks like someone literally drew a downward line from one side to the other, around 230 miles of cycling downhill along Route 66. There would be some lumps and the descent was actually only marginal, but it would be an easier day, or it should’ve been an easier day. The wind put an end to that.
We made it out of Amarillo and off into the countryside, again, loosely following I-40 for the day. It was a gloomy day too, although I was sporting some extreme tan lines, mainly to the right side of my body, so I wasn’t too worried about that.
To keep my mind focused each day, I tried to never think about how far in total I had to go. I focused on how long it was until my next stop, how long until my next feeding, how long until the next state, and so on. I had also downloaded many audiobooks to listen to. Today I was listening to Bear Grylls’ ‘Mud, Sweat and Tears’, a really motivating story about how he overcame adversity. Thanks for the ‘encouragement’, Bear.
There was very little to see here today other than more towns struggling to survive. It was amusing to see the Tesla charging stations around these ghost towns, given there was nowhere else to put them. If you’ve ever considered doing a road trip along Route 66 or wanted to ride certain segments, do it now. It’s very hard to see how the businesses will survive. I presume they are run by diehards who want to preserve the heritage.
As we approached Oklahoma my spirits lifted. Every new state was one state closer to the finish. Again, with the headwind, we weren’t going to make much distance up today, but another solid day in the saddle with 225 miles covered. More importantly, my mind and body were holding strong. Of course, it’s a daily occurrence to have the “why am I doing this” thoughts. I usually deal with this by letting my ego take over and thinking about what people might say or think if I quit. Our egos can be incredibly damaging to our persona, but sometimes they can be incredibly powerful too.
Stage Eight
Today’s stage marked the turn from cycling east to north-east along Route 66. This was a mental marker for me, almost like we were turning to head home, it was the last stretch.
Two big cities today, Oklahoma City and Tulsa. This meant that, in reality, we still might not bridge any of the distance we had lost, especially if those cities took time to get through.
Compounding that negative thought and, as we approached Oklahoma City, my gear cable snapped. The bike had done well, but I was glad that both my mind and body had made it further than the bike. Forgetting the two slow flats and one blow out I had on the tubeless wheels, the bike had survived a lot. For a few days previous, I had noticed my shifting was sloppy. I simply put it down to it being dirty.
Oklahoma City was great, a real pleasure and the support we had from people was incredible. People asking questions at lights, honking their horns. My mood was at an all-time high today. Chris took the Domane to be fixed, big thank you to Al’s Bikes for doing that so quickly and for just the cost of the parts. It was a revelation being back on the back-up bike though, my Trek Madone though. I had ridden the Domane, setup mainly for comfort, for so long that when I jumped on the other bike, in all its aerodynamic glory, it was a shock to be going so fast.
As we left the first major city of the day, we were riding busy back roads. This was a first for us, usually we were on quiet back roads, but now we were faced with having to manage traffic and not wanting to upset anyone. This was fine for a while, until the chase car got a flat. It was hardly surprising. You spend all day, every day riding the gutter or the dirty shoulder of the interstate, and you will inevitably get one. Somewhere we had gotten three nails in the tyre. This did mean that as soon as Chris brought my Domane back, he was off to fix the car. It also meant that I was now being chased by ‘The Meg’, the wide and 25’ long beast, which is less than suitable for chasing a slow bike cycling Route 66 on the busyier narrower roads.
As we approached the midway point in the day, I noticed a warm sensation in my right quad. Nothing like I had ever experienced before, and I wasn’t too worried at first and just kept on riding. I figured that I would have some injuries along this ride. As there was nothing I could do right then, I’d wait until my evening massage to address the situation.
As the light started to fade we made it into Tulsa. Tulsa is an amazing city, very artsy and beautiful. I enjoyed none of it. My leg had gone from moderate burn to stabbing agony. I had no power through that leg and now standing to relieve pressure on my injured under-carriage was causing significant pain on my damaged leg.
Unfortunately, as we left Tulsa, it became apparent that, due to a support crew mix-up, rather than 10 miles to go, we had 30. This was a real low moment for me, I knew I was in trouble with my leg and having an extra 20 miles to do was not good news.
Stage Nine
Although my leg did feel a bit better in the morning, it brought me to a standstill at a gas station around 20 miles into the day. It had given up. With Luis by my side, I sat down and drank a cup of gas station coffee. I text Chris and waited to be picked up.
It is at our lowest points where we are defined. Do we sit and stare into the distance, never knowing what it would be like to try, or do we pick ourselves up and give it our best shot? After several minutes of meditation, thought and reflection, I got back up, jumped on the bike and headed off.
The wind had given me a break, the sun had come out and, like a touch from the universe itself, I was revitalised. My energy and motivation returned and I was flying with a smile on my face.
I got about 30 miles further into the ride before my leg started hurting again. It was manageable, but pain killers were no longer helping me. The thought of what the large amounts of drugs were doing to my gut was frightening too. From that point, every 15 miles I’d need to stop and relax, but I pushed on to the century mark, where we met ‘The Meg’ just outside of Joplin and I sat to reflect.
I spoke to a physio friend, it wasn’t good news. What was almost certainly an elongated muscle wouldn’t get better while riding and could lead to serious complications later on. The modified pedalling style, to protect my ankle, was coming back to haunt me. Sure, I may have finished the stage in agony, but three more stages would be out of the question. It’s at times like these you need to be objective. One of the most powerful questions came from Luis, “what would I say if it was one of my clients cycling Route 66?”. My answer was fast and firm “I would tell them to stop”. And that was it…
The Aftermath of Cycling Route 66
One of the strongest motivators for me was being able to ride with Chris in Illinois near his mother’s grave. I was heartbroken that this wouldn’t happen, it was his one wish and he sacrificed a lot to get it. I insisted that we still stop and pay our respects. Then we went for an amazing dinner with his family.
There were two other items on the agenda; visit the Route 66 sign in Chicago and drop Luis off at the airport. After the first lay-in we had in over a week, we made this happen. I wasn’t as tired as I thought I would be. My ankle was sore to walk on, but my leg was feeling ok. Mentally, it was hard to be at the Route 66 sign without having cycled to it. Of course I was disappointed, but I was motivated too. Even within an hour of quitting, Chris and I were planning the second attempt in a year’s time.
One more night at a campsite near Chicago and we set off the following morning. A road trip that lasted about 30 hours to Las Vegas. ‘The Meg’ is a totally different beast when towing a car. To save two people driving, plus gas money, we rented a dolly and hitched up the car to the back.
We were all feeling pretty grim by the time we pulled into Las Vegas. A short turn around to get everything off the RV and I drove back home. If the theme of this trip was how big an influence the wind could be, it would be the same on the way back. Some of the wildest winds Nevada had experienced made driving the RV as difficult as it would be riding in it.
Of course, it was great to be home. Every night I would wake up and, dreaming, wonder where I am. I dreamt that I had been riding all day and we are pulling into a new location for the night. It took me a while to recognise that I was actually in my home. Perhaps that says something about having unfinished business…
Summary
This attempt did not end at the Chicago sign, but it taught me plenty about preparation, pacing, support, injury decisions and the value of unfinished business. If you are planning a demanding endurance challenge and would like help preparing sensibly, Book a Free Consultation. Please also feel free to reach out for any advice on cycling Route 66.
