Trail Running Calendar United States 2026-2027

An 18 mile out and back trail run from Windblown Ski Area toward Watatic Mountain Reservation, featuring steep, technical single track and uneven terrain. Prior trail running experience is strongly recommended.

Explore Lincoln State Park on trails and gravel roads. Choose from a marathon, 14K, or 5K distance, all starting together. The event features a scenic loop course with aid stations and a focus on environmental responsibility.

Experience a scenic 8k trail race through the forests and wetlands of Lake Conestee Nature Park. Run or walk a five mile loop featuring natural trails and boardwalks with views of the lake and local wildlife.

A 13.6 mile loop race starting and finishing at High Knob Observation Tower in Wise County, held Sunday September 20, 2026. The course runs mainly on Forest Service roads and proceeds support trail development in the Flag Rock and High Knob..

Trail half and full marathon at High Cliff State Park near Sherwood, WI featuring technical singletrack, prairie sections and views of Lake Winnebago, run as a cupless event with local park support.

Experience a 26.2 mile mountain run from Manitou Springs to the summit of Pikes Peak and back. This historic event features over 7800 feet of elevation gain and a 10 hour time limit.

The 30th annual Spoonbread Festival 5K in Berea KY offers a chip timed 5K on a flat paved trail, an untimed 1 mile fun walk, and a virtual 5K option with commemorative shirts and age group awards.

Experience the unique terrain of the driftless region at Yellow River State Forest. Choose from 5K 10K or half marathon distances and enjoy post race food games and sponsor giveaways.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

TAM Trek is a trail race and fun run in Middlebury, Vermont supporting the Trail Around Middlebury. Events range from a full 19 mile route around the village to shorter trail races and a family friendly two mile run.

A scenic five mile memorial run and virtual five mile option in Hinckley, NY, with a kids fun run included; proceeds fund a memorial scholarship for students pursuing medical studies.

An off-road 18.2 mile trail race with 2,609 ft of climbing through Paradise Valley and Emigrant Gulch, featuring creek crossings, three aid stations, marked technical terrain, and a finish at Chico Hot Springs.

Experience a unique 5K run through a scenic valley and a lit cavern in Alabama. Enjoy mountain views and a subterranean turn around point with constant cool temperatures.

A one mile loop elimination challenge in Webster NY on September 20, 2026 where runners must meet shrinking time cutoffs each mile; finishers receive a medal and category pins, with cash prizes for top male and female.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A 5K untimed fun run at Reclaimed Rails Brewing Company in Bondurant on September 20, 2026, with an open course that highlights Lake Petocka. Registration includes a craft beverage and series swag, plus music, food trucks, and games.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.