Trail Running calendar near Pine Ridge 2026-2027

Experience private trails and spectacular arch views at The Ascent in the Red River Gorge. Choose between the 5K and 10K distances for a rewarding trail event featuring significant climbs and professional timing.

A strategy-driven trail event at Paintsville Lake State Park where a marked half marathon course includes ten optional off-trail checkpoints with time bonuses. Two checkpoints are drawn mandatory at the start and skipping them creates penal..

The Zenith Adventure Trek will take place in Pine Ridge on Saturday 11 July 2026. You can run 20 miles.

An overnight relay event at Kroger Field in Lexington offering marathon, double marathon and 12 hour ultra relay options. Proceeds support cancer patient care and the event is cupless, so participants should bring their own cup.

Evening cross country races of 5k and 10k at Masterson Station Park on July 24, 2026, with music, food trucks and bourbon tastings. The 5k allows walkers and the 10k has a 16 minutes per mile cutoff.

A five kilometer trail race on the Flag Rock Area Trails in Norton VA held as part of the High Knob Outdoor Fest. Entry costs total $23.50 and proceeds support the festival.

A cross-country 5K and 10K at Talon Winery in Lexington with finisher awards and a wine drink ticket; under-21 participants receive the award but not the wine. The event includes wine sales, live music, and an after-party in the tasting roo..

A 2.5K trail race at Pulaski County Park on August 29, 2026, with a well-marked course and professional timing. The event also recognizes National Overdose Awareness Day and highlights local outdoor scenery.

GRC Cross Country Daniel Boone 5K is in Winchester, KY on September 5, 2026, with a down and back course from Lincoln and East Hickman to the country club. Entry fee is $30 and shirt registration is available until August 22.

A community Pride Run at Coldstream Park on September 19, 2026 featuring a chip timed 5K with awards and a 1 mile fun walk. Proceeds support local LGBTQ+ school programs and related resources.

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..

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.

A charity 5K at Coldstream Park/Legacy Trail in Lexington on September 26, 2026 benefits NICU babies, with an in-person chip timed 5K, a kids 1/4 mile dash, and a virtual 5K option with mailed shirts.

A trail 5K in Norton, Virginia held on the Flag Rock Area Trails as part of the Woodbooger Festival. Proceeds support the festival and the event is hosted by the City of Norton.

Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.

The Hellbender 10K in Norton, Virginia on October 3, 2026 is a 10 km uphill race that climbs from downtown to the 4200 foot High Knob summit with more than 2,000 feet of elevation gain. It is the 13th annual edition.

Experience a scenic trail run through the Red River Gorge on a private looping course. This cup less half marathon supports local search and rescue teams while offering a festive atmosphere with medals and post race meals.

Trail races in Shawnee State Forest on October 3, 2026 offering 54 mile, 50K and 13.1 mile options across remote singletrack with significant elevation gain and marked aid stations. The 50 Mile route includes a wilderness section called The..

Honor history at the Mogadishu Mile, a four person team obstacle course and one mile ruck run in Georgetown. Work together to complete 500 total reps and a weighted run without leaving any team member behind.

A second-annual fall 5K hosted by Gleaning Housing at Coldstream Park / Legacy Trail in Lexington, KY, with pumpkins for donors and snacks and drinks for all participants. Participants may bring or wear a pumpkin costume.