I’m traveling across the American West with my bicycle, documenting overnighters and short routes as I go. The first video in this series takes place in southern Colorado following the Aspen Loop Overnighter, a route winds through the San Juan Mountains to the historic Jersey Jim Fire Lookout Tower—a relic of the old U.S. Forest Service network that once dotted the American landscape. Watch it below, and then scroll down to some backstory about this project.

When I first started traveling by bike, every trip started at my front door in Chicago. I didn’t own a car back then. In Chicago, you don’t really need one; between the bike and the L, you can get just about anywhere. I rode to Milwaukee and Madison several times. I biked to Dubuque, Iowa, and back. Biked down to Gary, Indiana, and up to the Upper Peninsula of Michigan. I rode to Saint Paul, Minnesota, twice. Once, I just left home and let the wind decide which way I’d go. Four days later, I had looped deep into Wisconsin and found myself back in Chicago. When I’d run out of routes I could reach that way, I started taking the Amtrak. For a while, that opened things up. I even rode the train 47 hours to Seattle to start biking down the Pacific Coast. But without a car, every ride was a puzzle to get to and from the start. That’s how it went for years, until this fall, when I finally bought one.

When my parents told me they wanted to get rid of their old Civic, I bought it from them. For the first time, I could drive myself to routes instead of planning everything around train schedules. The narrow Yakima roof box that my dad used to haul gear north in winter became my sleeping space. A pad, a bag, a pillow, a light. It wasn’t much, but it worked. With the car, a new kind of riding opened up. I could do short trips and quick overnighters. I didn’t have to haul weeks’ worth of food and gear. I could travel lighter, plan better, and focus on the ride itself. It felt like a different way to bikepack—less burden, more joy.

As winter started closing in on Chicago, I hatched a plan. I called it the Loop of Loops. The idea was simple: make one big loop from Chicago—drive west, ride a series of smaller loops along the way, then circle back home. Each one would be a different BIKEPACKING.com overnighter, a new chance to ride, film, and learn. I wanted to document the routes for the community and, at the same time, teach myself filmmaking from the ground up. I’d studied photography and art history in school before spending 15 years in front of the camera as an actor and hand model. It felt like all the random paths I’d taken—photography, acting, travel—had finally converged into something that made sense.

The first stop on the Loop of Loops was the Aspen Loop Overnighter, just outside Mancos, Colorado. I left the Civic in town and pedaled 10 miles out to the start. The route was short—a little over 30 miles—but it had real mountain character: thin air, long climbs, and a backdrop of aspen and rock. It seemed like the right one to start with. A place to find a rhythm, to get used to filming and riding at altitude.

By early evening, I reached Twin Lakes, a small alpine basin tucked beneath Hesperus Peak. Two clear ponds, a thin ring of trees, and the sound of nothing but wind. I set up camp on a patch of grass above the water and watched the last light move across the face of the mountain. The air dropped below freezing fast. When night fell, the stars came out sharper than I could ever see in Chicago. It was one of the most beautiful places I’ve ever slept. The next morning, I rode down toward the Jersey Jim Lookout, an old fire tower from the late 1930s perched high above the forest. You can book it through the San Juan National Forest website if you’re lucky enough to find an open night. The tower still has its original furniture, including an old wooden stool with insulated legs. The rangers who worked there would stand on it with binoculars and scan the forest for smoke during lightning storms. From the bed inside, I could see nothing but sky in every direction. When the sun went down, I turned out the gas lanterns and lay there watching lightning flash over the distant peaks.

The next morning, I packed up, rolled back into Mancos, and loaded the bike onto the car. It felt good to have one loop finished—the first of many. Next, I’ll head west to California, where a whole string of overnighters are waiting. First up is the Basin and Batholith Loop in Mammoth Lakes, another chance to keep learning—about filming, about travel, about what keeps me drawn to this way of moving through the world.

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