Trail Running calendar near Brownsboro Village 2026-2027

Three trail races at Lincoln State Park on September 20, 2026: marathon (three loops), 14K (one loop) and a 5k on roads. The event supports park projects and includes aid stations, drop bag options, and organized registration through RunSig..

Run Baby Run 5K returns to Lexington's Coldstream Park and Legacy Trail with a flat, fast course and a Kid's Dash for young runners. All proceeds support the Snow Bunny Baby Project to buy diapers and wipes for NICU families.

A trail 10K at Raven Run Nature Sanctuary in Lexington on September 27, 2026, offering an in person field limited race and a virtual 10K with mailed shirts and no results submission.

Enjoy scenic 5K and 10K trail runs or walk and hike options at Deam Lake in Borden Indiana on October 3, 2026. Expect rolling climbs, creek crossings, multi use trails and reusable cupless aid stations for a sustainable race.

A trail run on October 10, 2026 in Gravel Switch, Kentucky. The 4K course winds through hills, meadows and woodland and includes a pancake breakfast plus handmade awards presented at the community shelter.

Join the first Running Pumpkin 5K in Lexington on October 17 at Coldstream Park and Legacy Trail, a fun autumn run hosted by Gleanings Housing to support affordable housing. Bring or wear a pumpkin and enjoy snacks and community spirit.

An annual trail running festival at Yellowwood State Forest on October 17, 2026, with distances from 8 miles to 50k including a 2-4 person 50k relay, festival camping, course maps and GPX files, aid station support, and post-race awards.

A 5K trail run at Shawnee Lookout Hamilton County Park on October 18, 2026, with a 3.44-mile course combining the Blue Jacket and Little Turtle loops and scenic river valley views. It is the final race of the Dirt Days Trail Series with age..

Join the Monster Dash in Bloomington for a fun 1 mile or 5K along the Karst Greenway Trail, where costumes, dogs and strollers are welcome. Enjoy free race photos and support the Auxiliary to the Boys and Girls Club.

The Deam Lake Winter Warrior will take place in Borden from Sunday 8 November 2026 to Sunday 22 November 2026. You can run between 6 and 4 hours.

A multi-distance trail event at PYOCA Camp near Brownstown IN featuring 10 mile, 50k, 100k and 100k relay options, live tracking for the 100k, cabin meal packages, well stocked aid stations and a 24 hour race cutoff.

A two day trail weekend at Camp Crooked Creek near Shepherdsville, KY, using a 12.7 mile loop with over 2,300 ft elevation gain per lap and race options from 5K up to 100 miles on December 5 and 6, 2026.

Trail races at Waverly Park from December 13 to December 27, 2026 offering 6.5 Mile and Half Marathon distances plus virtual options. Part of a Winter Warrior Series with course markings, on-course aid, awards, and a series medal for multip..