Trail Running Calendar United States 2026-2027

Join the Fall into Fall Trail 5k in Janesville on October 3 for a scenic run or walk along tree lined dirt trails. Stick around for the Fall Into Fall Heritage celebration with live music, food trucks and tastings.

Run the Charm Field and Trail Challenge on October 3, 2026, a scenic 5k plus a timed kids fun run through pastures, woods and country roads. Stick around for Charm Days festivities with food, a pony parade and community fun.

Join the Haunted Highlander 5k trail run for a spooky run, walk or ruck through haunted sets with actors and animatronics. Multiple heats plus a costume contest, bonfire and live music make it a festive night.

Join the new Community 5k at the 34th Annual Oxford Classic in Bend Oregon, a free, open to all loop through scenic Drake Park along the Deschutes River. Flat, wide paths make it ideal for a relaxed jog or lively pack racing.

The Bear Chase is a two day trail running festival at Bear Creek Lake Park on October 3 and 4, 2026. From ultras to fun 5K and 10K options, enjoy scenic single track loops with aid stations and live split tracking.

Run the True to the Brew 13.1 in Spartanburg SC on October 3, 2026, a point to point on the Croft Passage of the Palmetto Trail. Expect a technical, moderately hilly course best for experienced trail runners and hikers.

Run a challenging 100K through the wild trails of Cuyamaca Rancho State Park, featuring mountain ridges, desert views and stretches of the Pacific Crest Trail. This three loop course near San Diego is a Western States qualifier and a true t..

Run the FLATS Trail Half in Kirksville for 13.1 miles of single track, rocky climbs and lake views. Aid stations, shuttle service and a fundraiser supporting local trail building make it a lively community challenge.

Run the Arkansas Traveller 100 mile through the Ouachita Mountains near Perryville, AR. Expect 12,000 feet of climb, a 17 mile loop plus an 83 mile out and back, full aid stations and a 30 hour Western States qualifier.

Run scenic dirt trails and wide mountain views at the HRCA Wildcat Mountain Trail Races in Littleton, CO. Choose a 10 mile, 10K, or kids fun run and enjoy post race pancakes, medals, and a festive mountain day.

Join the Howlin' Coyote Canicross Trail Race in King George VA for a scenic, dog friendly trail run that benefits Friends of Caledon State Park. Enjoy varied terrain, reusable speedCups and the chance to race with your leashed pup.

Take on scenic new trails at Pocahontas State Park with a chip timed half marathon or 10K. Expect runnable singletrack, on course water stations, live results and race day age group awards in a festive park setting.

11 Miles to Paradise is a 10.6 mile point to point trail race along single track and forest roads beside the Clark Fork River in Lolo National Forest. Enjoy rolling hills, river views, shuttle service and a finish at Ferry Landing.

Celebrate Oktoberfest with a 5K Trail Run at Boal City Brewing in Boalsburg this October. Tackle scenic rolling trails and hills, enjoy a free brew if 21 or older, and stay for awards and a trophy engraving for overall winners.

Join the Kettle Cooker Five & Dime at Glenroy Preserve for scenic loop trails with 5 mile, 10 mile and 25K options over hills, creeks and rocky terrain. Chip timing, aid stations, a soft tee and post race beer make it a great day.

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

Join the 2026 FAAP Fall Classic at North Park on October 4 for scenic cross country races on park trails including part of the Rachel Carson Trail as autumn arrives. Proceeds support an orphanage in the Philippines with bamboo medals.

Join the SVdP Walk for Hope in Fort Wayne on Sunday, October 4, 2026 for a 5k or shorter loops around Parkview Field. Enjoy a community tailgate and help raise funds that directly support local families facing poverty and hunger.

Celebrate Day of the Dead in San Antonio with a scenic chip timed half marathon and shorter distances through parks and greenbelts, plus a costume contest with prizes. Finish with live music, Mexican food, and family friendly festivities.

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.