Distance: 36.2 miles
Set up shop at the swanky Oxford Hotel in downtown Bend. Across the street, Thump Coffee offers the most cycling-friendly breakfast in Oregon: munitions-grade, house-roasted espresso and Picky Bars – small-batch energy bars created by pro triathlete and Bend local Jesse Thomas. Thump also provides a perfect starting point for a loop beloved by Thomas and the dozens of pro, ex-pro, and wannabe-pro cyclists who call Bend home. Less than a mile beyond the city's 19th-century business district, you'll zip past kayaking runs on the Deschutes, hobby ranches tucked into the ponderosa forest, and breathtaking views on the climb to Mount Bachelor. "It's a great mixed-terrain ride," Thomas says. "Climbs, flat sections, technical corners, and not too many stop signs, so you can really get after it." A word of caution: Every Tuesday, a group of locals screams around the loop like a pro peloton. Resist the urge to join, says Thomas. "I consider myself a strong cyclist, and even I've been left behind by that crew. The Bend guys are legit."
More information: At the ride's end, choose one of Bend's 10 brew pubs to kick back – Thomas' favorite is 10 Barrel. Not winded? Climb aboard the Bend Cycle Pub, a multiseat bar on wheels.