In Good Company: Chiricahua Gravel with The Cycling House
Words and photos by Dave Malwitz
Dave Malwitz takes us along for the adventure through southeastern Arizona with The Cycling House and 7 other guests for the inaugural Chiricahua Gravel trip. The 5-day tour included four gravel routes that covered 180-miles of desert and Sky Island terrain including the area’s National Monument. Check out his recap and photos from the adventure below…
Rising dramatically from the desert plains of southeastern Arizona, the Chiricahua Mountains stand like an island of life against the horizon. Topping out just shy of 10,000 feet, this range sits at a remarkable geographical crossroads where the Sonoran and Chihuahuan deserts converge, while the Rockies and Sierra Madre mountain systems meet overhead. The result is a "Sky Island" ecosystem that stands apart from anything else in the Southwest. The northwestern portion earned National Monument status back in 1924, protecting a maze of towering hoodoos that has captivated visitors for the last century. While hikers and birders have been exploring this wilderness for decades, there may be no better way to experience its sweeping vistas, deep canyons, and rugged beauty than by gravel bike—a journey I embarked upon with The Cycling House, where every mile revealed new secrets of this extraordinary place.
The task of exploring a Sky Island that’s roughly the size of Maui might seem daunting, but The Cycling House (TCH) has mastered the art of making epic adventures accessible. Founded in 2005 in Tucson, Arizona, TCH has evolved from a winter cycling retreat into a premier provider of cycling experiences across the U.S. and Europe. Their approach to the Chiricahuas exemplifies what they do best: combining expert guidance with thoughtful logistics and warm hospitality. Each day's route is carefully crafted to showcase the region's dramatic landscapes, with knowledgeable guides who double as coaches, photographers, and bike mechanics. While riders tackle the mix of rugged gravel paths and scenic paved roads, TCH handles every detail—from gourmet meals prepared by professional chefs to carefully selected accommodations. This "we take care of everything" philosophy transforms what could be a logistically challenging expedition into a seamless exploit, allowing cyclists to focus solely on the joy of discovery. It's an approach that has earned them a reputation for creating not just bike trips, but immersive experiences where lasting friendships are forged over shared meals and tales from the trail.
Desert Foundations
A week prior to departure, trip leader Brendan Halpin reached out with detailed routes and final preparations for our 4-night/5-day tour. While The Cycling House has been crafting cycling experiences for nearly 20 years, their approach remains focused on quality over quantity. With just 80 carefully curated trips across the U.S. and Europe in 2024, the addition of a new destination speaks volumes about the potential they saw in the Chiricahuas. The region only recently appeared on TCH's radar when Brendan conducted a solo reconnaissance mission in the spring of 2024, discovering not only the perfect mix of gravel and paved routes but also securing an ideal home base for future trips. Our fall 2024 journey would serve as a pilot run for their 2025 season—a chance to fine-tune the experience while exploring the furthest reaches of this remarkable landscape.
After an eight-hour drive from San Diego, broken up with an overnight stop in Gilbert to meet up with Tim, we arrived at our accommodations for the week: The Painted Pony Resort. Tucked into 750 acres of New Mexico's high desert just outside the small town of Rodeo, this remarkable property carries its own fascinating history as the former private retreat of tech entrepreneur John MacAfee. The estate's five-bedroom main house and two guest houses would serve as our basecamp for the week. As the afternoon light played across the surrounding mountains, we explored the grounds, discovering a heated swimming pool, the outdoor fireplace, and a spacious patio perfect for gathering or stargazing under southwest New Mexico’s pristine night sky. The Painted Pony Resort offered a peaceful setting for recovery and connection after long days exploring the Chiricahuas by bike.
Our first afternoon set the tone for the days ahead. After settling into our rooms and watching the guides efficiently assemble bikes for those who'd flown in, we gathered in the garage for a 20-mile shakeout ride. As we rolled out from the property, the vastness of the landscape became more apparent—large grassy plains stretched in all directions, interrupted only by the commanding cliffs of the Chiricahuas to the west and the gentler slopes of the Peloncillo Mountains to the east. Apart from Highway 80, we found ourselves on a network of modest gravel roads interrupted only by the occasional fence crossing. I jokingly accused guide Michael Loomis of sizing us up during our arrival day spin. He then explained the importance of evaluating every rider’s equipment and capabilities to ensure our collective success over the full three days ahead. This attention to detail proved invaluable when one rider from Indiana experienced a double flat, prompting the guides to assist with a tubeless conversion that evening. The shakeout ride was the first hint that Brendan's earlier reconnaissance mission had paid off; what initially appeared as a region with limited potential was beginning to reveal itself after just a few hours in Rodeo. The following morning would begin our journey into the Chiricahuas, with each of the following three days designed to both challenge and accommodate riders of varying abilities.
Portal to Paradise
Our first full day took us on the 55-mile Paradise Loop, a route that lived up to its name. We set out from basecamp at a friendly pace, heading toward the small town of Portal, AZ—the appropriately named gateway to the Chiricahuas. As we climbed past 5000 feet, the landscape transformed dramatically, with towering rock walls and shaded roads lined by large trees that sheltered white-tailed deer and vibrant birdlife. The "Entering Paradise" sign welcomed us to what was once a bustling mining town, complete with saloons and general stores, now standing as a quiet ghost town. The climbing intensified, but we drew confidence knowing The Cycling House support van was never more than a few miles ahead.
Despite being strangers just a day earlier, our group naturally fell into a comfortable rhythm, each rider free to set their own pace as we regrouped at the summit. With the main climb behind us, we descended toward Cave Creek Canyon to the east for a picnic lunch prepared by Chef Liz Kenyon. Before the stop, guide Jon Cariveau, Suzanne, and I couldn't resist exploring the optional detour up Herb Martyr Road. Passing the Southwestern Research Center, we embarked on an investigation of our own, pedaling toward natural cathedrals of stone and discovering the true magic of riding in this wild landscape.
After lunch and a brief hike to Cathedral Vista, we returned to the Painted Pony Resort, where a delicious dinner awaited. The evening wound down with the group taking turns in the Normatec recovery boots, exchanging highlights from the day, and gradually retiring for the night. Before turning in, I stepped outside to marvel at the infinite expanse above—a chance to experience the Dark Sky that makes Rodeo a true stargazer's paradise.
National Treasure
Each day, Brendan updated our WhatsApp group with the final route details, building on the preliminary plans shared the week before. Day 3 was billed as the “Queen Stage,” promising an memorable experience: a point-to-point ride through the heart of the Chiricahuas. The day began with Chef Liz's signature breakfast burritos—a welcome sight, knowing extra foil-wrapped portions would be stashed in the support van for mid-ride fuel.
During the evening briefing on day 2, Brendan had sketched the route and elevation profile on the whiteboard, giving us a glimpse of what lay ahead: a 40-mile journey with 5,000 feet of climbing, anchored by an 11-mile, 3,000-foot dirt ascent to Onion Saddle right at the start. The next morning, we shuttled to Portal, where our bikes were unloaded and we lined up along Portal Road for a group photo. With guide Zeb Ruby’s countdown, we rolled out in unison.
Having descended Cave Creek Road on the Paradise Loop, we anticipated a challenging ascent to Onion Saddle. As we climbed, expansive desert vistas opened below while pine trees and autumn foliage lined the switchbacks above. Each turn revealed a fresh perspective on the jagged peaks framing our journey – a reminder that rides like these deserve a pace to observe and appreciate the moment. When I finally reached the saddle, I was happy to find the front group still gathered at the summit, sharing stories and snacks.
A technical descent followed, demanding careful handling around larger rocks while maintaining a low, stable position in the drops. The rough gravel eventually gave way to a flat stretch, but intense washboard tested both riders and equipment – dislodging two cameras along the way. The smooth pavement at the Chiricahua National Monument sign was a welcome relief, though it marked the beginning of our final challenge: an 8-mile, 2,000-foot paved climb. While staying alert to passing traffic, we took in the towering rock formations above.
The effort paid off at Massai Point, where Zeb awaited with chocolate chip cookies and cold Cokes. Standing at the summit, looking south over the forest of pines and dramatic rock pinnacles below, our sense of accomplishment was palpable – a long and demanding Queen Stage left us with memories as vivid as the landscape itself.
Southern Secrets of the chiricahuas
By the fourth day, our legs carried the honest fatigue of three days exploring the Chiricahuas, but anticipation for our final ride – another point-to-point route exploring its southern reaches – provided fresh motivation. We loaded bikes and riders into two vans, departing early for Rucker Canyon Road. This section had particularly piqued my curiosity; Strava heat maps showed virtually no activity in this part of the range, suggesting we were venturing into less-traveled terrain.
The day's destination was Douglas, Arizona, where lunch awaited at a historic hotel near the Mexican border. With tired legs, I was somewhat relieved to see the route profile showed a manageable 2,000 feet of climbing spread across 50 miles. Departing Highway 80, we pedaled across open plains where cattle roamed freely, with impressive rock formations never far away. Unlike some places where mountains remain distant teases on the horizon, here they always found a way to envelop us completely, their presence immediate and immersive with each turn unveiling new perspectives of red rock walls.
These lesser-known roads proved to hold some of the trip's finest riding. Guide Becca Clark and I rolled through a landscape of textured red cliffs, thick forest canopies, and undulating gravel hills. The solitude and raw beauty of this southern section felt like a fitting finale to our journey. After a final push toward the border along Leslie Canyon Rd, we arrived at the Gadsden Hotel, where a celebratory lunch awaited. Raising our glasses, we toasted to four days of discovery and our collective achievement in traversing this remarkable range.
Four days of riding in the Chiricahuas proved to be the perfect duration to explore this remarkable place. Each day pushed us to our limits while somehow leaving just enough in reserve for the next day's adventure. By our final push to Douglas, we collectively emptied our tanks, sharing those last challenging miles to the border town as a unified group – exactly as we'd started.
While the benefits of a guided gravel trip might seem self-evident, the true value of The Cycling House experience revealed itself in unexpected ways. Covering 180 unique miles of the Chiricahuas was physically and mentally demanding enough; having expert guides handle everything else – from shuttles and route planning to maintenance and nutrition – elevated the entire experience immeasurably. Instead of worrying about logistics, we found ourselves gathering around evening fires, sharing stories over Chef Liz's remarkable meals at a communal table, and focusing solely on the pure joy of riding. The expertly curated routes and comprehensive support allowed us to fully immerse ourselves in the rugged solitude and dramatic landscapes.
When I asked the group about their favorite day, opinions varied widely – each rider connecting differently with the unique challenges and experiences of each route. While we couldn't reach consensus on the best day, we unanimously agreed on two things: we would deeply miss Liz's cooking, and the Chiricahuas had permanently etched themselves into our gravel-riding memories. For those inspired to experience this remarkable corner of Arizona for themselves, The Cycling House has several Chiricahua Gravel trips planned throughout 2025. Like us, you'll almost certainly discover that this dramatic Sky Island far exceeds expectations, offering one of the richest cycling experiences imaginable.
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