Trail Running calendar near Milan 2025-2026

Celebrate the new year with the First Day Trail Run and Walk at Monroe Lake, an untimed, non competitive trail event. Choose from three scenic distances, enjoy hot soup and a warming fire, and support Monroe Lake programs.

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 Caesar Creek State Park with marathon, half and 10K on wooded single track trails. Bring a headlamp and collapsible cup for aid stations and earn a glow in the dark owl finisher medal.

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.

Hit the trails at IW2R Winter Trail XC, a scenic 5K on the groomed cross country course at Northview Church in Carmel. Snow or sloppy conditions are possible, so bring proper footwear and help support course upkeep.

Run the FroMoMoFo on January 11, 2026 in Morgan Monroe State Forest, choosing a 10 mile fun run or the UTMB Index 20 mile on the scenic Three Lakes loop. Enjoy cozy on course aid stations with fireplaces and daylight only racing.

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.

Louisville Lovin' the Hills in Fairdale, KY on February 7, 2026 offers 50K, 15 Miler and 6 Miler options on scenic single track forest trails. Enjoy pasta at packet pickup, a wooden finisher medal and post race soup with fellow trail runner..

Run or ruck through scenic woods around a peaceful lake with a 5k single loop or 50k ten loop option. Rustic aid stations, hot soup, and a campground bonfire make this a cozy trail challenge.

Join the Indiana Trail Running Association for a relaxed winter trail run and social in Yellowwood State Forest near Nashville, IN. Choose a roughly 6.5 to 7 miles lakeshore loop or shorter options, then warm up by the fire with soup, sandw..

Take on scenic trails at Mounds State Park on March 7, 2026 with 5K and 15K options as part of the DINO Trail Run Series. Enjoy river views, ceremonial mounds, on course aid stations and heated facilities for a comfortable race day.

Join the Holliday Park Trail Run, a two day spring celebration with family activities and a day of scenic trail races for all ages. Tackle rugged woodland trails, cheer kids in fun runs, and support local park programs.

Run the Scout Run on March 21, 2026 in Lebanon, Ohio, with an in person or virtual 5K on scenic trail loops. Hosted by Boy Scout Troop 186, the event supports local projects and offers shirts and medals for early registrants.

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.

Hit the Pate Hollow trails at Paynetown State Recreation Area on April 4, 2026 for a scenic, hilly trail run offering a 15K single lap and a shorter 5K. Challenging terrain and forest views make this a perfect early season test.

Tackle the Knobstone 50, a rugged 50 mile ultramarathon through southern Indiana's forested Knobstone Trail with roughly 10,000 feet of climbing. Enjoy scenic single track, shuttle service, and a recycled performance hat for all starters.

Enjoy 3.6 miles of winding trails at Ault Park, with a railroad trestle and a stretch of pioneer road providing a scenic, historic backdrop. Chip timing, refreshments, and a friendly vibe make this series stop a great spring outing.

Scenic single track awaits at the Backside Trail Marathon and Half in Louisville's Seneca and Cherokee Parks. The marathon is two loops on gently rolling trails, so wear trail shoes and expect slower times than on roads.