Trail Running calendar near Pine Ridge 2026-2027

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

Trail 5K and new 10K on private property near Natural Bridge Campground in Red River Gorge with packet pickup, awards, shirts and medals. A virtual option includes a commemorative shirt and finisher medal for a donation.

Overnight running relays and ultramarathon events at Kroger Field in Lexington on July 18 to 19, 2026 raise funds for cancer patient support care. Options include marathon relays, a double marathon relay, a 12 hour ultra, and a survivors wa..

A cross-country 5k and 10k at Masterson Station Park on July 24, 2026, and the first race in a three-event series. Participants receive a race shirt, finisher award and a bourbon tasting ticket; under-21s do not receive tasting tickets.

A 5K trail run on the Flag Rock Area Trails in Norton held as part of the High Knob Outdoor Fest. Entry fees support the festival, awards go to the top three men and women, and all participants receive a 2026 festival T shirt.

An evening of trail races at Pulaski County Park in Nancy, Kentucky, offering distances from 5K up to a 36K stage race, plus relay and combined-entry options. Registration windows and fees are listed for several events.

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..

Freedom 250 2.5K Trail Race at Pulaski County Park on August 29, 2026 features winding trails and rolling hills. The event acknowledges National Overdose Awareness Month and lists a $25 registration fee.

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.

Woodbooger 5K is a 5K trail race in Norton Virginia held on the Flag Rock Area Trails as part of the Woodbooger Festival. The three day festival spotlights local natural resources, folklore and history and benefits the festival's continuati..

Dingess Tunnel and Trail 5K is a 3 miles running event on September 26, 2026 in Dingess, West Virginia that passes through the historic Dingess Tunnel built in 1892. Registration includes a free official Dingess Tunnel & Trail 5K T shirt wh..

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.

A 10K road race in Norton, Virginia, climbing more than 2,000 feet up to the 4,200 foot High Knob summit on October 3, 2026; entry fee is listed at USD 43.50 and registration closes October 1.

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.

Loop trail races in Shawnee State Forest on October 3, 2026, with 54 mile, 31 mile and 13.1 mile options, significant elevation gain, cupless aid stations and a remote wilderness section.

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.