Some trails have historical significance, and others are fun to ride — but combine the two, and you have something truly special. The Timberline to Town Trail not only highlights some critical moments in Oregon’s history, but it’s also a blast, starting at treeline on the state’s most iconic mountain and descending 4,400 feet through an increasingly lush landscape. (less)

Those whoops and hollers in the woods at Sandy Ridge aren’t Bigfoot but your fellow riders expressing their overwhelming joy. You can see it in their loam-eating grins as they blast back into the trailhead after rallying an unending collection of deep berms, blazing fast straightaways, and chunky rock gardens. (less)

This is one of the top routes in the state, offering a bit of everything: tough climbs, scenic traverses through flower-laden alpine meadows, and a fast, hair-raising descent to finish the ride. The highlight, though, is the unparalleled views of the backside of Oregon’s iconic Mt. Hood, seldom seen by most visitors to the state. (less)

Without any heartbreaking climbs, this loop allows you to get in the groove of a wonderful slice of PNW scenery. Mostly circumnavigating the namesake lake, the trail provides plenty of swimming opportunities and shots of Mt. Hood to the north. Bring a cooler full of food and drinks, and make a day out of your visit to this relaxing destination. (less)