Trail Running calendar near Gravel Switch 2026-2027

A June 20 nature run at Loretto Motherhouse offering 5K, 10K and a virtual 5K. The course goes through woodlands, lakes and grassy trails, walkers are welcome and proceeds support the Loretto Community.

Trail event at Turkey Run Park with a timed five mile race with awards and a timed three mile fun run. Proceeds support Second Chances Wildlife Center and the course features single track wooded trails and a midway water stop.

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.

Experience a weekend of outdoor sports at McDougal Lake with trail runs and mountain bike races ranging from 4 to 32 miles. Compete for podium spots or enjoy the party lap at this multi discipline trail festival.

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..

A 31 mile supported road event on July 12, 2026 in Elizabethtown KY with finish at Brandenburg waterfront park. Entry is limited to 50 runners and requires verified experience, crew support, and reflective safety gear.

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 fundraising running event at Red Orchard Park in Shelbyville supporting The Dream Factory. Timed 3 hour, 6 hour and 12 hour events plus a 6 hour team relay take place on a two mile cross country course.

Charity 5K at River Front Park in Brandenburg, KY with in-person and virtual options. Proceeds support medical expenses for a 10-year-old boy; registration fees vary and a guaranteed race shirt requires registration by July 17, 2026.

Trail runs in Iroquois Park with 7 mile and 4 mile options as part of the Kentucky Cryptid Series. Complete three of four races in-person or virtually to earn a Cryptid Series survivor medal and shirt.

Muddy Princess Kentucky is a 5K obstacle mud run in Glencoe on August 16, 2026, offering standard, VIP and volunteer options and supporting the National Breast Cancer Foundation with on site photos, hydration points and a rinse off station.

A 12 hour trail event at Saunder Springs Nature Preserve in Radcliff, Kentucky, offering solo, two person, and four person team options on a loop course that mixes technical and runnable trail with waterfalls and creekside sections.

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.

Experience a unique trail race through the historic Blackacre Nature Preserve featuring wooded paths and farm animal sightings. Choose between 4 or 8 mile distances and enjoy post race ice cream at the historic homestead.

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 trail stage race on the Knobstone Trail with 5 mile, Half Marathon, 18 miler and a new 50K option; proceeds support the Suicide Awareness Mission and local scholarship grants.

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.

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.