The trails at Perry Hill were first cut out of the rocky southern end of the Worcester range in 1998 by former local shop owner Hardy Avery. Avery says the first trails weren’t so much “built” as they were scratched through the brush of Vermont’s Green Mountains. Snow, rain and mud are common in this steep terrain, and if the area isn’t choked with lush ferns, it’s sloshing with Vermont’s trademark foliage—conditions to test the constitution of any trail. “But these days everything is bench cut and sustainable and well-armored,” says Avery, who now owns Sustainable Trailworks, a for-hire trail-building business. Although most of the network lies on state land, the legality of the Waterbury trails has been cloudy, but favorites like Rastaman, Burning Spear and Joe’s have survived the years. The best (and most challenging) trails are on the upper section of the network, where the land is steep and rife with sheer rock faces, jagged granite fins and slickrock sections. Avery’s old shop, Irie Cycles (now called I-Ride), has moved to nearby Stowe, and a new Waterbury shop called Five Hills Bikes has helped carry on the torch. Working with the state through the Vermont Mountain Bike Association and the Stowe Mountain Bike Club, the trails were finally declared legal to ride in 2006.

Contingent to its newfound legitimacy, the area holds more than a dozen bridges within its 15 miles of trail, most installed to protect vulnerable areas. “They’re not North Shore skinnies, but they get you from to A and B with minimal impact on the land,” says George Wisell, owner of Five Hills Bikes. “And if you fall off them you’re just as hosed because it can be an 8- to 10-foot drop.”

—Chris Lesser