Trail Running calendar near Winslow 2025-2026

Challenge the Ouachita Switchbacks in Big Cedar Oklahoma on January 17, 2026 with 50K, 25K or 10 Miler options over extremely technical, hilly singletrack. Remote trailhead, rock glacier views, great swag and a lively post race party await.

Take on chilly singletrack at the Frozen Toes Trail Races in Kessler Mountain Regional Park on January 24 with a technical 15K or a family friendly 5K. Finishers get socks and a medal plus warm soup and a beer for participants 21 and older.

Join the 10th annual Greenleaf Trail Run on January 31, 2026 at Gruber ORV Park in Braggs OK, offering 5, 10, and 20 mile trail loops over moderately technical terrain. Finishers get custom medals and top three in each race earn trophies.

Celebrate the 10th annual GTR on January 31, 2026 at Gruber ORV Park in Braggs, Oklahoma with looped trail runs over moderately technical terrain. Choose a 5 Mile, 10 Mile, or 20 Mile course and earn a custom finisher medal and trophies for..

Peak to Creek is a rugged, scenic 33 mile 50k single loop near Cookson OK on Feb 7, 2026, with about 4,500 feet of climbing and possible creek crossings. Limited to 70 runners, finishers within cutoff earn animal themed buckles and all entr..

Run scenic 2 mile loops to a hilltop overlooking Lake Vian during a weekend of distances from 4 miles to 100 miles, including marathon and ultramarathon options. Chip timing with live lap counts, finisher medals and a buckle for 100 milers.

Join the Passion Play Trail Run at The Great Passion Play grounds in Eureka Springs for scenic trail courses from a fun run to a half marathon. Enjoy finisher medals, aid stations, finish line snacks and a ticket to see The Great Passion Pl..

Run rugged Ozark trails around Lake Leatherwood in a 120 mile team trail relay April 10 and 11, 2026 in Eureka Springs, Arkansas. Teams of 4 to 8 share the course as each runner completes three trail legs totaling about 15 miles.

Honor veterans at the Trail of Honor Memorial Run in Fort Gibson, OK on May 23, 2026 while supporting permanent flag pole installations. Take part in a USATF certified 5k or a 1 mile fun run and carry a flag as you go.

KROP returns to Welling Ridge Trails near Tahlequah OK for a rugged looped trail challenge on rocky, root twisted single track with big climbs. Choose short loops or ultramarathon distances in a timed 12 hour event that supports local trail..

Pumpkin Holler Hunnerd is a fall gravel and trail weekend near Tahlequah OK, with ultras and the Gravel Smasher. At Eagle Bluff on the Illinois River, hilly gravel courses, solid aid and campfire finishes support Activate Oklahoma.

Hare Mountain 100 is a point to point 100 mile ultramarathon on rugged Ozark Highlands Trail singletrack, passing creeks, waterfalls and the summit. Expect roughly 20,000 feet of climb, remote aid and required satellite tracking.

Experience rugged beauty on the Ozark Highlands Trail at Hare Mountain 100 in northwest Arkansas, a UTMB Index race featuring waterfalls, bluffs and big climbs through hardwood and pine forests. Distances include 100 mile, 50 mile and 60k,..