Trail Running Calendar United States 2026-2027

A community ultramarathon and hike at Skyline Wilderness Park in Napa, CA, featuring a 3.3-mile loop repeated up to ten times in an hourly format to raise funds for the Pheo Para Alliance.

Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.

A community running event in San Marcos on September 26, 2026 offering a 10K competitive race, a 5K fun run and a free kids trot, with race shirts, wooden medals and an on-site expo.

Trail ultramarathon in Milford, PA offering 50K and 25K courses along the McDade Trail beside the Delaware River. The mostly flat, non technical route has three aid stations and is a cupless event.

Upstate Strut for Childhood Cancer on September 26, 2026 at Milliken Arboretum features a 5K and a 1 mile fun run to raise funds for children with cancer. The event includes race shirts, team competitions, and age group awards.

A 7.1 mile mountain trail race at Jay Peak, Vermont with about 3,044 ft of vertical and a technical summit ridge. The field is capped at 500 runners and the course is clearly flagged with a strict summit cutoff.

A timed 5 mile trail race at Lincoln Parish Park in Ruston, LA, featuring part of the lake loop and about four miles of trail on the day of a park festival. Overall male and female winners receive special awards.

A point to point trail race from Vail to Minturn with 26K and 14K courses across Vail Mountain. Both routes feature alpine singletrack, scenic views of Mt. Holy Cross, staffed aid stations and a post race lunch voucher.

Experience a timed multi surface race along the Santiam River in Stayton. Choose from 10K, 5K, or 3K distances and celebrate your finish with a commemorative pint glass at a local brewery.

A 3.1 mile obstacle run with 22 symbolic obstacles representing the journey from captivity to liberation. Held in Happy Valley, OR on September 26, 2026, all proceeds support organizations that fight human trafficking and survivor rehabilit..

Trail races through prairie, woods, and a bluff in Big Sioux Recreation Area near Brandon, SD on September 26, 2026. Distances include 5 miles, 2 miles, and a free kids race, with chip timing and series points awarded.

A trail running event at Conservation Park in Panama City Beach on September 26, 2026 that raises funds for the St. Andrew & St. Joseph Bay Estuary Program. Distances include a Fun Run, 5K and 10K on mixed trail and boardwalk terrain.

An urban multi-loop running event in Tulsa on September 26, 2026, featuring marathon through 100 mile options. The unmarked 25 mile loop requires map navigation, uses QuikTrip aid stops, and has a 34 hour finish cutoff.

The 13th Annual PINK OUT 5K & 1 MILE in Macon offers in-person chip-timed and untimed 5K options, a 1 mile family walk, and a virtual 5K window to raise funds for United in Pink's survivor support programs.

A multi distance running event in Tampa with a half marathon, 10K, 5K, 1 mile, kids dash and virtual option. Features include chip timing, designer shirts and finisher medals, with youth pricing for ages 12 and under.

Experience the rugged terrain of Claude Texas at the Conquer the Canyon Trail Race. With distances ranging from 5k to 100k plus a youth run there is a trail course for every distance preference.

A *5K* trail run on Town of Breckenridge Trails that finishes at Blue River Plaza on Main Street during Breckenridge Oktoberfest. Field limited to 300 runners; first 250 registrants receive a long-sleeve technical tee and 21+ entrants get a..

Trail trail races in Greensfelder County Park, Wildwood MO on September 26 2026. Distances include a 53K and a 13.1 mile half marathon with a ruck division on technical, hilly single track with manned aid stations and a cup free policy.

Timed six hour and twelve hour events on a two mile lakeside loop in Evanston, IL. Finishers receive a can of Hop Water and a handmade award, with two aid stations and multiple water fountains along the course.

A free, third annual six hour trail run in Louisville GA on a 2 mile single track loop with technical wooden trail, creek crossings and short climbs. Personal lighting is required and a single aid station and participation medals are provid..