Trail Running Calendar United States 2026-2027

Run On The Rocks in Point Of Rocks, MD on September 26, 2026 features 10 mile, half marathon and 20 mile events. The race is chip timed and includes participant shirts, finisher medals and age group awards.

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.

Double Peak Challenge in San Marcos on September 26, 2026 offers 10K, 5K and a free Kids Trot plus a race expo and awards.

A 50K and 25K trail event on the McDade Trail in Milford PA, out and back along the Delaware River with three aid stations and a cupless course.

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.

Trail racing at Jay Peak on 09/26/2026 covering 7.1 miles with 3,044 feet of vertical gain, multiple competition divisions, timing with disposable bib chips, aid station hydration, race prizes and points toward 2026 season standings.

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 options across Vail Mountain, high alpine singletrack, staffed aid stations and postrace awards.

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 at Big Sioux Recreation Area near Brandon SD featuring 5- and 2-mile courses plus a free kids mile, chip timing, and series points by age division.

Third annual trail run in Conservation Park Panama City Beach on September 26, 2026 supporting the St. Andrew and St. Joseph Bays Estuary Program.

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.

Community fundraiser in Macon with in-person 5K options, a 1 mile family run, and a virtual 5K window; proceeds support United in Pink's survivor assistance across Central Georgia.

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 races at Greensfelder County Park featuring a 53K, a 13.1 mile trail half marathon and a ruck division on technical singletrack with aid stations and a 10 hour limit.

Timed 6 and 12 hour events on a 2 mile lakefront loop in Evanston with two aid stations, public water fountains, nearby parking, and a nonalcoholic finish beverage and finisher award.