Trail Running calendar near Winter Park 2026-2027

We have found 112 Trailruns within 80 miles of Winter Park. See below where and when you can find the races.

Run Rabbit Run in Steamboat Springs, Colorado is an annual trail ultramarathon offering 100 mile (Hares and Tortoises) and 50 mile divisions, limited-field races with a six-figure prize purse and a history of charitable giving.

A trail race in Golden, CO featuring a 10-mile North Table Loop with bonus miles and a 5-mile route on Lithic Trail and Fairmount Canal Loop. Organized by BeyondHome to support families moving from homelessness to self-sufficiency.

Expo Park XC is an old school grass cross-country meet in Aurora, Colorado, featuring creek crossings, a wooden footbridge and bale jumps. Races range from about 1 km for young children to a 5 km open race.

Experience the wild spaces of Northern Colorado with a weekend of trail races ranging from a half marathon to a 50 mile ultra through scenic forests and scout camp trails. Stay on site with available camping and community meals.

Experience desert style single track and forest roads with views of the Collegiate Peaks in Buena Vista. Choose between 50k or 30k distances as part of the multi sport 14er Fest.

A 24 hour loop endurance run on a 0.82 mile circuit atop the Palmer Divide in Palmer Lake, Colorado at 7,240 feet. Top overall finishers receive awards and early 100 mile finishers receive buckles; part of fees supports local parks.

A two-day trail and bike event in Estes Park featuring 31-mile bike and run options, a 15-mile heavy half, and a 62-mile duathlon, with rugged trails, significant climbs, and aid stations supporting competitors.

A scenic half marathon from Fanny Hill in Snowmass along the Government Trail through Aspen groves to Koch Lumber Park in downtown Aspen. Registration opens April 28, 2026; in store $80, online $105.

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.

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..

A fall trail event in Buena Vista, Colorado on September 27, 2026 offering a 14K trail race with over 500 feet of elevation gain and a 5K along the Arkansas River. Both races start and finish at Vendor Village near the Eddyline Beer Garden.

October 2026

A weekend trail endurance festival at Bear Creek Lake Park (Oct 3–4, 2026) offering distances from 5K to 100K on mostly singletrack, with looped courses, staffed aid stations, drop-bag access at the Start/Finish, and finishers' awards.

Experience the scenic HRCA Backcountry Wilderness Area with trail races for the whole family. Enjoy rolling hills and open views followed by a pancake breakfast and finisher medals for all participants in Littleton.

A Woodland Park trail event featuring 50k and 10k options on singletrack and forest roads with views of Pikes Peak, stocked aid stations, and crew access for the 50k.

Experience the scenic single track trails of Steamboat Springs during the Emerald Mountain Trail Run. Choose between the 4 mile or 12k distances through aspen groves to support the local Boys and Girls Club.

A multi distance trail festival in Castle Rock featuring a family adventure run plus 5K, 10K, half marathon and 50K ultramarathon across Philip S. Miller Park and Ridgeline Open Space. Events include chip timing, finisher medals and aid sta..

A six-hour trail challenge in Littleton where runners complete a 5K each hour for six hours, totaling 18 miles if completed. Trail terrain, hourly elimination, tiered patches and medals, and national leaderboard prizes highlight the format.

Participate in a Halloween themed trail run through the scenic paths of Aspen to support the local animal shelter. Pets are welcome to join the race in costume for a chance to win special prizes.

A fall trail race at Staunton State Park offering 50K, 25K, a 25K FishSlappers division, and a steep 5K, run on runnable singletrack with aid stations and fundraising for land and water conservation.

Trail races near Sedalia, Colorado on October 17, 2026 with 50 mile, 55k, 15 mile and 5 mile options through montane forests and red rock terrain. Limited field size, aid stations, drop bag access, camping by reservation, and specific pacer..

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