Tucson, the Chiricahuas, and 20 Seasons of Riding

For the past 19 years, our winters have revolved around Tucson, Arizona. It’s where The Cycling House was born, and in many ways, it’s still home. This past winter marked our 20th season in Tucson, a milestone that has us reflecting on how far we’ve come.

Back in 2005, The Cycling House was born out of a simple idea: bring passionate cyclists together in an incredible location, offer top-tier support, and create an experience that feels like home. Tucson became our launchpad, and two decades later, it remains the heart of what we do.

Over the years, Tucson has hosted thousands of riders, from weekend warriors to brand-new cyclists. What keeps people coming back year after year isn’t just the riding; it’s the atmosphere. It’s the laid-back morning coffee, the stories told over dinner, the encouragement on the climbs, and the high-fives at the end of a long day in the saddle.

For us, Tucson represents more than just a season—it’s our foundation, our family, and our favorite place to ride bikes in the winter. We’re proud to call it home, but we knew we were ready to add an addition to our family.

Last year, we asked our guests: What format, when, and where would you like to see a new trip? The overwhelming answer? Gravel-focused. Late winter or early spring. Domestic.

For us, the answer was clear: The Chiricahuas.

You probably hadn’t heard of them until we announced the destination—and we liked it that way. The Chiricahua Mountains are the perfect contrast and complement to Tucson. This stunning, rugged range is the tallest and most remote of the Sky Islands, sitting on the Arizona-New Mexico border just a stone’s throw from Mexico.

Check out our fall trip dates here!

The Sonoran Desert stretches endlessly until it suddenly rises into these mystical peaks. There’s a powerful, almost spiritual energy in the Chiricahuas. Unlike Tucson, there’s no urban sprawl here. Just vast, wild land that makes you feel small in the best way. The riding is raw and rewarding. By the end of each day, you’re proud of what you’ve accomplished. The Painted Pony Resort becomes an oasis, and our chefs serve up the best food you’ll find for a hundred miles.

Days at Chiricahua Gravel Camp are simple. Life slows down. People unwind. It’s a refreshing break from the busyness of the outside world. The nearest town is Portal, Arizona, and in many ways, this trip is a portal: into a slower, deeper, more connected way of being, even if only for a few days.

But the Chiricahuas aren’t for everyone, and that’s okay.

Just three hours away, we’re still offering our award-winning road and gravel trips from our Tucson house. Mt. Lemmon and Saguaro National Park remain staple rides, and our Tucson property—the only one we own—continues to feel like the ultimate home base.

This season in Tucson was one of our biggest yet. We hosted road and mixed-terrain trips, training camps, returning and new guests, private groups, and even one wedding. It was another epic season, made incredible by our amazing guests and the best staff in the business. Every year, we feel deeply grateful to be doing this work we love—creating experiences that fill our hearts.