Bucket List Goal: Cycling the Length of Route 66 — Bam! Done!

This trip would not have been possible without the encouragement and support of my husband. From buying the maps back in 2015 to green-lighting my absence from not one but two young kids, he has mercifully allowed me to ease into adulthood at my own pace.

In that vein, I also have to thank my mother-in-law, who did the real work while I was away, and my dad, who accompanied me for half of the journey. Thanks also to my brother for outfitting my dad for his big adventure, and to my mom for cooking the food that fueled me.

My dad and the spread waiting for me at a park.

To my friends Nelson and Marisa, thank you for inspiring me to actually do this trip. To Katy, thank you for showing me how to train for it. And to Dan and Sara, thank you for making the final stretch feel like a bike ride in the park with friends.

Outside Village Cycle Center in Chicago, IL.

I also want to express my gratitude for the amazing independent bike shops along the route, especially Village Cycle Center in Chicago; Sun Adventure Sports and Hill's Sport Shop in Amarillo; The SpokesMann in Kingman; and The Bike Shop Santa Monica. These businesses are the lifeblood of cycling. They serve cyclists without questioning the crazy adventures we dream up, and they're filled with people who have hard-earned experience and practical advice to share. This is especially valuable in smaller towns where there may not be many other resources available. I also want to give special recognition to Single Track Bikes in Flagstaff, whose service and expertise went above and beyond. I share more details in my Day 12 post.

Part of what made this trip such an incredible experience was the people living and working in the towns along Route 66. Yes, the route's heyday has passed, but there is still a tremendous amount of energy and enthusiasm surrounding it.

An adorable ‘Roadside Attraction’ in Dwight, IL

Seligman was a particular gem in my eyes. It felt like a town being lovingly rejuvenated by a younger generation invested in preserving and celebrating its history. The motel where I stayed was one example of that spirit. So was the roadside museum in Dwight, Illinois. The model train depot in McLean, Illinois, was another memorable stop.

Two other places that stood out were Tulsa, Oklahoma, and Springfield, Missouri. Both cities felt youthful and energized. Possibilities seemed boundless, and there was a sense of optimism in the people I met that was genuinely contagious.

The thing that was most surprising to me? California has shit roads! New Mexico, surprisingly, has great roads!

What I would do differently

Perfect Is the Enemy of Progress

My friends Marisa and Nelson encouraged me to stop inventing roadblocks and excuses. Instead, they encouraged me to embrace my midlife crisis, which ultimately saw me buying a bike sight unseen and riding for the first time in six years the day I arrived in Chicago.

Was that intelligent? No.

Should I have trained? Absolutely.

But if I had waited until I felt completely ready, I might never have done the ride at all.

Training Is Not Cheating

That said, if I were to do this again, I would spend at least three to four months training, building up to 80–100-mile rides in windy, wet, and hot conditions.

When I look at photos from 2019, I see a lot of preventable suffering. For the 2025 ride, I spent several months riding distances of up to 60 miles with elevation gains that mirrored what I’d actually face on the road. It paid off. Despite riding through terrain that was far less hospitable, the trip itself felt much easier.

The First Half Is Better

While the desert offers undeniable desolation, isolation, and romance, the stretch from Chicago to Amarillo was a much better, more scenic ride. It features more parks, more water, and far better preservation of the historic route itself. Next time, I would allocate more time to enjoying this first half, despite the increased traffic and population density.

Tubeless Tires (Don’t think twice)

Get them.

Yes, you'll need to carry sealant and a few extra supplies. But you'll avoid repeatedly stopping on the highway to replace tubes punctured by the tiny steel wires shed from semi-truck tires.

At one point, I was carrying five spare tubes because I had no idea where the next bike shop would be.

Learn Basic Bike Maintenance

Which brings me to maintenance.

I am not a bike mechanic. I have very basic skills: I know what most of my tools do, and I can change a flat. On the road, I typically stopped into a bike shop every 400-500 miles. For my comfort level, it was okay not to be an expert; if I had waited to master mechanics, I would have never left the driveway.

However, that lack of confidence was the exact reason I initially skipped tubeless tires. I erred by sticking with what was familiar instead of adopting what was categorically better.

Pack Minimally, If You Can

This depends on your travel philosophy—and, frankly, your budget—but I found a minimalist setup to be ideal.

I rode a road bike rather than a traditional touring setup. I stayed in hotels, ate at restaurants, and carried only one change of clothes.

There was something incredibly liberating about it.

I didn't need racks or panniers. Instead, I used a frame bag, a handlebar bag, and a seatpost bag, all of which worked perfectly with a full carbon frame.

Nutrition Matters

In 2019, I fueled myself primarily with cola, Swedish Fish, ice cream, and burgers.

Six years later, I discovered that age has opinions.

For the second trip, I had to be much more intentional about nutrition and recovery. If you have the opportunity, I would recommend meeting with a sports nutritionist beforehand. Understanding the type and amount of fuel your body actually needs can make a significant difference over the course of a long ride.

Skip the SAG Wagon

For most riders, a support vehicle is unnecessary.

Unless you're attempting something highly specialized, Route 66 is accessible enough that you can travel self-supported and still find the services you need along the way.

Have Faith

Faith in people. Faith in yourself.

Pop culture—whether it’s the movie Se7en or True Detective—would have you believe that every small town is harboring a serial killer. Out on the road, that couldn't be further from the truth.

I found a world filled with kind, friendly, and generous people. Strangers routinely showed up right when I needed help the most, even if it wasn't the exact technical help I required.

Sometimes you are entirely capable of solving a problem on your own, but just having that first person pull over and ask, “Are you okay?” is all you need to remember that the world cares.

Finally, on a massive ride like this, things rarely go according to script. You will inevitably find yourself facing a brutal, 110-mile day through a baking desert. In those moments, you must maintain absolute faith in yourself. Doubting your capability when things look worst is a distraction at best—and at worst, it will eat you from the inside out.

Go out and see what you’re made of.

What I Learned from Cycling Route 66