Trail Running calendar near Greencastle 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.

Run the Kennekuk Road Runners Siberian Express, a 7.45 mile winter trail through Kickapoo State Park with steep climbs, creek crossings and wildlife. First 150 finishers receive awards and post race festivities are at Vermilion Brewing.

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.

Bop to the Top Stair Climb in Indianapolis challenges all ages to conquer 36 floors and 780 steps in OneAmerica Tower on Jan 17, 2026. Choose single, triple or team entries to support Riley Children's Foundation while testing your strength.

Take on the Frozen Cock's Crow 5K, a wintry route through rugged, steep trails at Willenborg Woods near Charleston, Illinois. Expect technical climbs, friendly trail support and a warm post race celebration to reward your effort.

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.

OPSF 50|50 is a trail running weekend in Owen Putnam State Forest near Poland, offering 50M, 50K, 14 mile and 10K on a rolling, technical 14 mile loop. This cupless event requires runners to carry 20 oz of water and awards finisher medals.

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.

Run rugged Brown County trails at Dances with Dirt Gnaw Bone on May 16, 2026, featuring steep ridges, technical singletrack and big elevation changes. Distances 5K to 50M plus relay, finisher medal, awards and post race barbecue.

Test your grit at the Peace Officer Memorial Endurance Ruck, choosing a 4 hour endurance or 5 km trail ruck on a mostly unpaved one mile loop. Bring your own rucksack loaded to 10 percent of body weight and enjoy a supportive, family friend..

Hit the trails at Brown County State Park for the DINO Trail Run, with 5K and 15K routes over scenic, hilly mountain bike trails. Expect tough climbs, a fast downhill finish, and a free kids race for the whole family.

MoMoFo offers a rugged trail 100 km through Morgan Monroe State Forest with big climbs, old growth trees, lakes and rock features, plus a scenic 20 mile loop. Both UTMB index races welcome virtual entries and include event swag.

Join the 28th annual Lake Mingo Trail Run on June 13, 2026 at Kennekuk Cove County Park, a scenic 7.1 mile loop mostly on natural trails with rolling hills and nine bridges. Celebrate afterward with food, beer, and great trail camaraderie.

Take on a rugged 5K at Willenborg Woods in Charleston with winding trails, a one third mile river crossing and about 1,100 feet of climbing up Billy Goat Hill. Field is limited to 125 and finishers get pancakes and ice cream.

Run a scenic 10k around Stryker Lake at Griffin Bike Park with rolling hills, wide trails and two friendly laps that make passing easy. Camping at Fowler Park and the concurrent DINO Gravel Triathlon create a lively event atmosphere.

Hit the Wild Wild Wilderness at Kickapoo State Recreation Area on September 12, 2026 with 5K or a rugged 7.45 mile trail through woods, steep climbs and creek crossings. Celebrate finishes with food, drinks and awards.