I Biked Hundreds of Miles Alone on My Birthday—and I Can't Wait to Do It Again

I challenged myself to a solo physical challenge. Here's what I learned

A man cycling in a beautiful Oregon state forest setting on the road to Larch Mountain. He has a bright blue street bike that stands out from the green of the surrounding trees. He looks up the road ahead as he pedals hard downhill, getting in some training for upcoming races. Motion blur on the road as he speeds down.

Ryan J Lane / Getty Images

We're dedicating our April features to all things solo travel. Whether it’s a soul-searching hike, a decompressing beach trip, or an invigorating urban getaway, tackling the world as a solo traveler has become safer, easier, and more empowering. Dive into this month's features to learn strategies for making friends while solo and the ways technology has changed the solo travel experience, then get lost in inspiring stories of bus journeys through Africa, a voyage to Mount Fuji, a social experiment in South Korea, and a solo bikepacking birthday celebration.

It was raining in Coos Bay, Oregon, again. Over the past five days, I’d cycled more than 550 miles and 24,000 feet of elevation gain by myself, with everything I needed to survive attached to my bike. And I was over it.

Sometime in my early twenties, I’d created a birthday tradition with myself: do a solo physical challenge that would test my mental, spiritual, emotional, and physical fortitude. It started reasonably simple—I’d bike the 40 miles between my house at college to my parents’ house, or I’d run as many miles as the age I was turning. When I lived in Colorado, I’d hike and ski a 14er (a peak of more than 14,000 feet). When I moved to California’s Bay Area, I’d bike and run to the top of Marin County’s Mount Tamalpais from Stinson Beach or bike to the East Bay’s Mount Diablo from my home in Berkeley and then drive back to the base to run it.

I only had two requirements for these birthday challenges: the first, it had to be an actual challenge, and the second, I had to do it solo. So as I was approaching the major milestone of my 30th birthday, I figured I’d need to concoct the most formidable birthday challenge yet. 

The mission I came up with was simple in theory (and much more challenging in practicality): I’d fly to Vancouver, British Columbia, with my carbon fiber road bike and minimum camping gear and ride back to my home in Berkeley—a more than 1,000-mile journey.

But as I woke up on my sixth morning into the trip to another downpour on Oregon’s central coast, I was starting to reconsider the journey and everything about it that I’d wrapped up into my own identity.

I was breaking perhaps the most critical rule of outdoor adventure: Don’t do it by yourself.

Cycling continues to be one of the most popular outdoor recreation activities in the U.S. The Outdoor Foundation estimates that nearly 53 million Americans older than age 6 (about 17.3 percent of the population) participated in cycling in 2020, higher than any other year since the foundation has been tracking the data. According to the same data, more than a quarter (28 percent) of youth aged 6 to 17 years old participated in cycling in 2020, making it the most popular outdoor activity in that age group.

According to Outdoor Industry Association data, trip-related spending around bike tourism accounted for about $83 billion in economic impact in the U.S. alone. That data also found cycling as one of the fastest-growing outdoor activities years before the pandemic created a flurry of panic-buying bikes. Read: If you or someone you know hasn’t talked about bike touring or bikepacking, it’s only a matter of time.

As I was conjuring up this solo mega-trip in the months before my 30th birthday, my friends and family made it known that they weren’t as keen on it as I was, especially since I would be on my own. It made sense. They didn’t want me to get hurt, and I was breaking perhaps the most critical rule of outdoor adventure: Don’t do it by yourself.

But I was hellbent—while I love the connections that form when adventuring with a partner or group, I also adore the bonds formed between myself and the natural world while adventuring solo. I believe that everyone should take a solo trip or adventure at least once, and hopefully, what I learned from my journey can help you plan one of your own.

Start Simple

As an endurance athlete and outdoors enthusiast, I spend a lot of time outside. It’s familiar and comfortable to me. For first-time solo adventurers, though, my advice is to start simple. Try a solo overnight camping trip. Then move on to an overnight backpacking trip. If you have a planned goal (like a multi-day solo bike touring or bikepacking trip), work towards it slowly; spend a night or two solo with the exact setup you plan to use before committing to the entire trip. 

Prep and Know Your Gear

Preparation is crucial. I spent days at my local bike shop with the head mechanic, prepping my bike and learning how to fix it should anything go wrong. (It did.) Because my bike touring trip was on main roads and through towns, it had lower consequences if something did go wrong. It can be easy to forget what solo means, as odd as it sounds. If a snafu occurs, you’ve only got yourself to get out of it. 

Prepping also means knowing the gear you’ll be using. The bike I used was my regular road cycling bike. I’d already ridden thousands of miles on it and knew it well. I also purchased the gear I’d be using on my trip months and even years in advance (bivvy bag, bike bags, backpacking stove, sleeping pad, and bag).

Know Why You’re Doing It

Purpose is also huge. (And this might’ve been my downfall—more on that soon.) Maybe that purpose is simply getting a night in the wilderness by yourself. Or perhaps it’s a months-long existential mission. Perhaps it’s for a killer Instagram story. No judgments here. I just strongly recommend having a set intention or purpose and meditating on it as you set out.

Highway 101 winding along the Pacific coast in Oregon

@ Didier Marti / Getty Images

Let Others Know Your Plan and Practice Safety

Remember the number one outdoor adventure rule? Never do it alone? Well, if you do, rule number two is to let at least one other person know your plan and whereabouts. I really can’t emphasize this enough. Let someone know when you’re leaving, when you’ll return, and everything in between. I have a good friend who is one of the best alpinists, mountaineers, and outdoor adventurers I know. His motto? Live to climb another day. Whatever your outdoor adventure choice is, make sure you live to do it another day.

You’re Rarely Actually Alone

I met and was around many interesting people during my bike touring trip—other cyclists, restaurant and market staff, others at campgrounds, families at breweries, etc. No matter what you’re doing, there are almost always other people around you. They might be strangers, but they’re also humans that likely share at least some common interests and values.

Bailing Is Fine

As I began cycling south out of Coos Bay, the rain continued to pour. My trip wasn’t going as planned. I had taken a wrong turn in very rural Washington, adding 10 miles to an already planned 120-mile day. I literally learned the phrase “white-knuckled” as I crossed the Columbia River Bridge into Astoria, battling through howling winds as a storm slammed the coast. My gear wasn’t drying. I had saddle sores on top of my saddle sores. And I’d learned a landslide had closed my planned route in Northern California. In short, my romanticized solo trip had turned into a suffer-fest.

So I bailed. 

It was something I’d never done before in an outdoor pursuit. Again, as an outdoor enthusiast and endurance athlete, I pride myself on suffering well. But as I left Coos Bay, I was over it. So I turned around. Since I was on my bike and by myself, I was limited on my return options. My only option was to backtrack and bike from the coast to Eugene and hop the Amtrak back to Berkeley. 

I learned a valuable lesson as I took the ride of shame back home, informing my friends and family of my failed mission. Having grace with yourself is invaluable. There’s no greater way to show yourself love than showing yourself grace. And adventuring solo, too.