As the seasons change and the days grow shorter up north, we know it’s time to head South to our winter playground: Tucson, Arizona. This year is especially meaningful — it’s our 20th season of hosting cycling trips in the Sonoran Desert. Two decades of pedaling through saguaros, sharing big desert skies with friends old and new, and welcoming riders into The Cycling House family.

A Trip Built on 20 Years of Experience

When we first rolled out in Tucson, we had one thing in mind. Escape the Montana winters. The thought of hosting trips around the world hadn’t crossed our minds; we were simply looking for sunshine, good roads, and a winter escape. Over the years, we’ve fine-tuned every detail: the routes, the house itself, the meals, and the community. Guests can expect fan favorites — like Mount Lemmon and Saguaro National Park to be a part of the itinerary. Both offer a glimpse into the Sonoran Desert landscape with beautiful vistas on two bucket list rides.

We know these roads like the back of our hands, which means you can simply show up, pedal beautiful routes, enjoy family-style meals, and let us take care of all the details. Our team takes great pride in making each week special and unique – we know time is precious, and we are grateful to have the opportunity to host guests year after year in our old favorite, Tucson, Arizona.

Why Tucson is perfect for Winter Riding

While the rest of the country is bundling up, Tucson offers a different story. Winter brings mild, sunny days, with average highs in the 60s–70s °F (15–25 °C). It’s the kind of riding weather cyclists dream of — warm enough to ride in shorts, cool enough to climb comfortably, and almost always dry. Don’t worry if you start chilly, we have a support vehicle to collect layers, offer mechanical and nutritional support, and cheers as you log winter base miles.

The desert landscapes are strikingly beautiful in winter: soft morning light on the Catalina mountains from the back patio, golden sunsets looking towards Gates Pass, and the perfect, comfortable home base nestled in the Northeast corner of Tucson. Whether you’re here to build early-season fitness, escape the snow, or simply ride your bike in a place that feels alive, Tucson delivers.

Early Winter 2025

• 10/29-11/2/2025: Tucson Road (4 Night) – 1/2 Full
• 11/4-11/9/2025: Tucson Road (5 Night) – Almost Full!
• 11/11-11/16/2025: Tucson Gravel (5 Night) – 1/2 Full
• 11/18-11/23/2025: Tucson El Tour (5 Night) – Fully Booked/Waiting List!
• 12/3-12/7/2025: Tucson Women’s Gravel (4 Night) – 1/2 Full
• 12/10-12/14/2025: Tucson Road (4 Night) – Almost Full!
• 12/7-12/21/2025: Tucson Gravel (4 Night) – 1/2 Full
• 12/31-1/4/2026: Tucson Road (4 Night) – Fully Booked/Waiting List!

Winter 2026

• 1/7-1/11/2026: Tucson Road (4 Night) – 1/2 Full
• 1/20-1/25/2026: Evolve Triathlon (5 Night) – Fully Booked
• 1/28-2/1/2026: Tucson Road (4 Night) – Fully Booked
• 2/3-2/8/2026: Tucson Road (5 Night) – 1/4 Full
• 2/10-2/15/2026: Tucson Women’s Gravel (5 Night) – 1/2 Full
• 2/17-2/22/2026: Tucson Gravel (5 Night) – 1/2 Full
• 2/24-3/1/2026: Tucson Road (5 Night) – Almost Full!
• 3/3-3/8/2026: Peak Coaching Group (5 Night) – Fully Booked
• 3/10-3/15/2026: Tucson Gravel (5 Night) – 1/4 Full
• 3/17-3/22/2026: Tucson Road ( 5 Night) – 1/4 Full
• 3/24-3/29/2026: Tucson Road (5 Night) – 1/2 Full
• 3/31-4/4/2026: Tucson Road (4 Night) – 1/4 Full
• 4/7-4/12/2026: Peak Coaching Group ( 5 Night) – Fully Booked
• 4/14-4/19/2026: Tucson Road (5 Night) – 1/2 Full

Check out the entire year’s trip calendar.