Cycling & running events in Bend, 2026

Bend Base Miles

Running: Locals run the Deschutes River Trail when they want dirt, water, and easy miles from town. The Deschutes River Trail near Old Mill gives a three-mile-or-so loop from Farewell Bend Park. Shevlin Park covers the soft stuff, and the Shevlin Loop Trail runs 6 miles with around 290 feet of gain. Pilot Butte brings the punch, with its singletrack gaining about 500 feet in less than a mile. Central Oregon Running Klub handles Thursday miles, Saturday coffee runs, and Sunday long runs. FootZone brings Tuesday Performance Group intervals. The Bend Marathon and Half, Bigfoot 10k, and FootZone Bend Classic Mile anchor the calendar.

Cycling: Locals ride everything here: road, gravel, mountain, fat bike, and cyclocross. Central Oregon Wheelers runs group rides, and Bend Area Cycling Enthusiasts has a large riding group. Bend Bikes backs the town bike scene, and COTA keeps the singletrack sharp. Phil's Trail Area covers the MTB base, while Oregon Trail Gravel, Twin Bridges Loop, and Westside Tour handle Z2 and dirt days. The Mt. Bachelor/Cascade Lakes Loop starts from Downtown Bend and gives almost 3,500 feet of sustained climbing. Bachelor/Cascade Lakes Loop starts from Downtown Bend and gives almost 3,500 feet of sustained climbing. 8% average gradient. Oregon Trail Gravel, Cascade Cycling Classic, United States National Cyclo-cross Championships, and USA Cycling Elite Road National Championships sit on the race radar.

Season: Autumn usually gives Bend the best training window, with warm dry days, cooler nights, and that annual Indian summer feel. Summer turns the high desert dial way up, and the daily temperature swing approaches 35°F, so locals start early and keep the easy days truly Z2. The Deschutes River and Shevlin Park feel especially good when the exposed land gets hot and dry. Winter brings snow, colder December days, and a different rhythm for both sports. Central Oregon Running Klub shifts Thursday runs to Crosscut Warming Hut and keeps Hot Chocolate Runs going downtown. Riders lean into dry-day gravel, fat bikes, and whatever the organizer has lined up.