The Cloudcroft Gran Fondo is a full weekend affair — road on Saturday, gravel on Sunday — with three distance options on the road day so you can right-size your suffer. The Gran Fondo heads east on US 82, swings through the Mayhill loop, then points south on the Sunspot Highway all the way to Timberon before the return finish at Upper Karr Canyon. The Medio cuts the day short at the Sunspot Observatory turnoff. The Petite does the Mayhill loop and turns around at what the locals call Six Mile. All three share the same 10am start, which is a genuinely thoughtful touch for anyone driving up that morning.
This is the Sacramento Mountains at their most dramatic — high-desert pine forest, sweeping highway rollers, and the kind of elevation that makes the air taste different. The Sunspot Highway in particular is one of those roads that feels like it was built specifically for bikes: quiet, scenic, and relentless. Upper Karr Canyon as a finish line means you're earning every bit of it.
Sunday's gravel edition flips the script entirely, starting down in High Rolls rather than up in Cloudcroft — but the organizers are running an escorted peloton descent from town at 8:30am so you can keep your car parked up top. Two distinct events, one long weekend in the mountains, and Skratch Labs at the aid stations so you're not rationing warm water out of your jersey pocket.