It's a rare thing for me to travel to the same place twice. With vacation time scarce, the pull to explore a new area overwhelms any desire to return to the same place. Oaxaca—a state in Southwest Mexico—is one of the few places where I found myself scheming a return trip before I’d even arrived home.

Along with being an amazing cycling destination, the capital city is filled with wonderful food and colorful neighborhoods. The surrounding countryside is a mix of intimidating mountains and fertile valleys where indigenous cultures still flourish amid the well-preserved ruins of their ancestors. You can spend days touring artisan villages where each has mastered a skill that serves as a contribution to the broader Oaxacan culture: Teotitlán is known for handmade textiles, Santa María Atzompa for its pottery and Santiago Matatlán for its Mezcal.

Taco Run: Matt takes on Oaxaca

Cass Gilbert, a longtime contributor, has documented routes in the Oaxacan area for several years. His routes all seem to strike the perfect balance of adventure/cultural exploration—and I chose a route that seemed to showcase the central valley and surrounding mountains: The San José Del Pacifico Grand Dirt Loop. This route forms a 244-mile loop with an impressive 24,500 feet of climbing and conveniently departs and ends from the city center of Oaxaca. I’m a sucker for any route description that uses the word “backcountry.”

Day 1: I pedaled out of town on Friday with a strict deadline to be back in Oaxaca City by Monday night to pick up my girlfriend from the airport. When your girlfriend says, “No excuses, you better be there when I land.” You know that you better be there. I quickly realized this would be a hard route to rush. Around every corner was an impressive street art mural, a group of locals huddled around a taco stall or a row of towering cacti and beautiful flowers to be enjoyed amid a backdrop of striking mountains. I rode for 6.5 hours, 54 miles to the village of Santa Marta Chichihualtepec. The town was empty, but I followed loud music to the central square and cathedral. It was there that the villagers were gathered, adults drinking free beer & mezcal and the kids eating ice cream. There was traditional dancing by villagers in elaborate costumes. After enjoying the party for a bit, I found there wasn’t a hotel and with the sun descending quickly, I scampered out of town to find a quiet spot in the surrounding countryside to camp for the night.

Day 2: I pedaled through increasingly mountainous terrain to reach the namesake city of the route, San José Del Pacifico, a mountain town with a growing tourist infrastructure to support adventures in the surrounding mountains. It was also my only opportunity en route to snag a hot shower and a bed for the night. 8:15 moving time / 57.20 miles / 7,766ft.

Taco Run: Matt takes on Oaxaca

Day 3: My favorite stretch of riding. The landscape and terrain reminded me of the Eastern Tennessee Cohutta Wilderness. Similar to Cohutta riding, the elevation profile is deceptive. You’re tricked into assuming you won’t climb much, only to be confronted with relentless, punchy climbs and descents. This section really showcased Cass Gilbert's dedication to exploring and connecting obscure dirt roads. Up to this point, the route passed through a village with enough frequency that there was never a concern about keeping my framebag filled with food. Running on fumes, I mistakenly passed a few opportunities for resupply and ended up descending into the village of Santa María Zoquitlán. I was hoping to find accommodations but was looked at quizzically when I asked for a hotel. Once again, sunset found me scrambling to find a safe campsite. 8:50 moving time / 70.90 miles / 8,816ft.

Day 4: The final push to finish back into Oaxaca City. The second half of the route when followed counterclockwise is more remote and more physically demanding. I descended into the valley that links back to Oaxaca. Cass Gilbert's determination to avoid all paved roads was really evident in this final stretch. Being tired and close to town, I was tempted to avoid the final section with a shortcut. Fortunately, clearer thoughts prevailed and I settled in for the final stretch of farm roads and some singletrack through fields of agave, corn, and beans.

Taco Run: Matt takes on Oaxaca

This trip to Oaxaca really showcased what’s possible with my Litespeed Pinhoti III hardtail. I was able to take one bike for all our adventures: bikepacking on rough gravel roads, burly singletrack in Sierra Norte, and causal cruises around town. The Pinhoti III's durability and resilience made it easy for me to pack it safely away in a bike box under the plane and not worry about it arriving in one piece. While I finished the route in 3.5 days, the recommended 5-7 days would be ideal. The locals all move at an enviously unrushed pace, and I often felt foolish working so hard to make it back to town in my allotted time.

If you’re interested in planning your trip to Oaxaca, Cass Gilbert’s personal blog is an excellent resource for everything Oaxaca: day rides, longer bikepacking routes connecting Oaxaca Central to the beautiful coastal beaches, and even a bikepacking food guide to the region.

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Matt Schweiker is an endurance rider and Litespeed ambassador. He can often be found aboard his Pinhoti III in the backwoods and fire roads near Chattanooga TN, or tackling bikepacking routes abroad.