A Hiking Wonderland

Ashland, Oregon  

by Matt Wastradowski 

Back in the 1980s, Ashland-area mountain bikers fell in love with a forested trail on a ridgeline just south of the city. The path cut through a mix of ponderosa pine, madrone and—in one area—so much manzanita, it forced riders to duck down and get low on their bikes. More than a few likened the experience to pedaling through a tunnel. Several described the experience as “going down the rabbit hole” and eventually christened it the Alice in Wonderland Trail in honor of Lewis Carroll’s seminal work. 

The name stuck, and more than three decades later, the wider Alice in Wonderland network of hiking, mountain biking, and equestrian trails is among the city’s best-loved outdoor attractions—all just five minutes from downtown. 

Officially, the trails are known as the East Side Forest Lands—some of which were old, disused wagon roads dating back to the early 1900s. But today, the Alice in Wonderland trails (as they’re more commonly known) bear fanciful names inspired by that first mountain bike path—like Cheshire Cat, Caterpillar, White Rabbit, Jabberwocky and Queen of Hearts. Taken together, the trails connect Siskiyou Mountain Park, Oredson-Todd Woods and lands managed by the U.S. Forest Service. (Some of the paths also pass through private property, so be sure to stay on the trail at all times.) 

More than a dozen miles of trails live up to their enchanting names with natural wonders around seemingly every bend. The magical paths crisscross open grasslands, cut through narrow glens, ascend and descend rolling hills, and offer remarkable views of downtown Ashland, nearby Grizzly Peak and the surrounding Rogue Valley. Downhill mountain bikers continue to frequent the Alice in Wonderland Trail today, as it’s one of the network’s few practical descents, while hikers generally prefer the winding nature of the multi-use White Rabbit Trail. 

With so many entry points into the system, a mixture of pedestrian-only and mixed-use paths, and the occasional unsigned junction, hiking and cycling can feel almost as confusing as Alice after falling down the rabbit hole. 

Whether you strap on the helmet for a rip-roaring ride or opt for an easier stroll in the shade, chances are good you’ll have a reaction similar to Alice: “Curiouser and curiouser!” 

You can download a trail map from the City of Ashland website. Plan your Ashland lodging, dining, entertainment and more at travelashland.com.