Bend
Trail Running Calendar near Bend 2026-2027
Explore the top trail runs near Bend for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
April 2027
Four low key evening trail races around Bend, Oregon with courses of 4 to 7 miles and overall series standings for runners completing at least three races.
May 2027
Trail 5k, 10k and half marathon at a vineyard near Terrebonne with vineyard views, alpacas and a complimentary wine glass for registrants.
Overnight and day loop racing at Cline Buttes with 3/6/12/24-hour options, a Last Person Standing format, and a 5k on a 3.1 mile loop with a steep climb.
Spring trail races of 50 mile, 50K, and 10 mile through Smith Rock State Park and Crooked River Grasslands near Terrebonne, Oregon.
July 2027
A multi discipline endurance festival in Bend, Oregon featuring a 13.1 mile trail run, 39 mile mountain bike race, 55 or 39 mile gravel ride and three person team racing.
Two point to point ultramarathons from Bend to Sisters offering a 100 mile and a 50 mile option, mountain trails, multiple aid stations and a 32 hour cutoff for the 100 mile.
August 2027
September 2027
Three Sisters Skyline in Sisters, Oregon features a 50K through Ponderosa forests to the Three Sisters Wilderness and a point-to-point half marathon with a net downhill.
October 2027
A community 5K within the long-running Oxford Classic, this flat mixed-surface loop in Drake Park follows the Deschutes River and is open to all ages.