Trail Running calendar near Milan 2025-2026

Join the Krazy Krampus 5K in Indianapolis on December 5, 2025 for a festive, costume friendly run with a mischievous Krampus character and colorful awards. Proceeds benefit the Pike Township Distance Program and winners receive Krampus orna..

Run scenic, rugged trails in Jackson Washington State Forest at Jackson County Ultras on December 6 with 10 mile, 50k, 100k and team relay options, laps that pass lakes and ridgetop views. Indoor post race comfort and buckle awards for 100k..

Run the Topo Trail Marathon at East Fork State Park on December 7, 2025 with quarter, half and full options on a 6.55 mile singletrack loop. Enjoy aid stations, a race tee and a finisher medal on a scenic course.

Run the Waverly Winter Warrior at Waverly Park in Louisville on December 14, choosing a 6.5 mile trail loop or a half marathon. Part of the Winter Warrior Series, the event rewards every finisher and offers bundle discounts for multiple rac..

The First Day Trail Run and Walk will take place in Bloomington on Thursday 1 January 2026. You can run between 3 and 4 miles.

Kick off the year with the Resolution Run, a scenic trail half marathon at Caesar Creek State Park in Waynesville, Ohio. Part of the Wolf Pack 2026 series, it mixes rugged singletrack and park scenery for runners seeking a new start.

Kick off the year at Caesar Creek Trail Race on January 3, 2026, with options from 5K to half marathon, a 6 hour challenge and a 20K relay hosted by Wolf Pack Trail Runs. Scenic trails, aid, plenty of parking and leashed pets welcome.

Run under the stars at the Night Owl Trail Marathon, Half Marathon and 10K around scenic Caesar Creek State Park. Expect wooded single track, rolling hills and fun aid stations for a challenging and memorable night trail experience.

Run under the stars at Eagle Creek Park in Indianapolis on January 10, 2026, tackling nearly all single track loops by headlamp. This sold out night trail features chip timing, small wave starts, and a finisher medal for those who finish.

Take on scenic single track trails in Morgan Monroe State Forest with 10 mile and 20 mile options on January 11 in Martinsville, IN. Aid stations with fireplaces and hearty race fare make this a cozy winter trail challenge.

Join the Bop to the Top Stair Climb in Indianapolis on Jan 17, 2026 to conquer 36 floors and support Riley Children's Foundation. Choose single, triple or team climbs and get a long sleeve shirt.

Shelby Trails in Simpsonville KY on January 17, 2026 showcases scenic trails through pastures, rows of cedars and wooded creek bottoms. Choose a 4 mile loop or tackle two laps for an 8 mile challenge on mixed grass, dirt and single track.

Run single track forest trails in Fairdale near Louisville on Feb 7, 2026 with 50K, 15 mile, and 6 mile options. Finish with soup and a wooden medal, and enjoy a packet pickup pasta dinner the night before.

The Lake Of The Woods 50K will take place in Farmersville on Saturday 7 February 2026. You can run between 5 and 50 kilometers.

The Holliday Park Trail Run will take place in Indianapolis from Friday 20 March 2026 to Saturday 21 March 2026. You can run between 3 and 5 miles.

Run the Scout Run in Lebanon OH on March 21, 2026: an in person 5K on scenic mixed surface trails or a virtual 5K from anywhere. Support Boy Scout Troop 186 and register early for a commemorative shirt and finisher medal.

Run or walk the Valley Vineyards Wine Run 5k through scenic vineyard trails and a bike path on March 28, 2026 at Valley Vineyards Winery & Brewery. Finishers get race swag, a wine stopper medal and a post run wine pour.

Knobstone 50 on April 11, 2026 is a point to point 50 mile trail race through rugged southern Indiana with roughly 10,000 feet of climbing along the Knobstone Trail. Registration closes April 3 and pacers are allowed for the 50 mile field.

Join the Backside Trail Marathon in Louisville's Cherokee and Seneca Parks on April 26, 2026, with marathon or half on scenic single track. Medals for all finishers and a Double Down award for back to back weekend runners.

Run the DoNot Stop Half Marathon in Indianapolis on April 26, 2026, featuring a half marathon, 10K, 5K, 1 mile and Kids Dash plus a virtual option. Chip timing, custom finisher medal, designer shirt and finish line donuts make it a fun, fam..