Trail Running calendar near McHenry 2025-2026

Join the Ugly Sweater 5K at Helicon Brewing in Oakdale for a festive flat out and back on the Panhandle Trail, plus a 1 mile fun walk. Finishers get medals and the first 150 5K registrants score a free ugly Christmas hat.

Kick off the year on the trails with Chill in the Hills, a New Year's Day 5k run or walk at Bridge Sports Complex in Bridgeport WV. Early registrants snag a free event beanie and the race joins the Bridge to Victory Race Series.

Kick off the year at the New Year's Resolution Run in Oakdale, PA on January 1 with a flat, fast 5K on the Panhandle Trail and a family one mile walk. Register by December 31 to claim a commemorative coffee mug for the first 150 and run wit..

Winterfells Challenge is a January Strava event where runners score points for miles and climbs. Pick the 13 mile Full with six climbs or the hill focused 6 mile Mini and compete on the leaderboard. Frozen Goat Challenge on February 7 invi..

Winterfells Challenge is a January Strava event where runners score points for miles and climbs. Pick the 13 mile Full with six climbs or the hill focused 6 mile Mini and compete on the leaderboard. Frozen Goat Challenge on February 7 invi..

Free, nonprofit run in Pittsburgh on March 7, 2026: a roughly 30k urban route that climbs 50 city staircases across the Northside. Low key and self supported, donations go to Riverview Park programs.

Run a scenic 4k or 8k on the rolling grounds of Twisted Oak Farm Brewery in White Post, VA. Enjoy chip timing, a finisher medal, a tech shirt and a complimentary glass of beer, with a virtual option available.

Soles for Songs 5K in Oakdale, PA supports the South Hills Children’s Choir scholarship fund. Run a scenic out and back on the Panhandle rail trail from Helicon Brewing, then enjoy refreshments and community spirit.

Choose a 10K course or a hillier half marathon at the Dirty Kiln Trail Races in Canoe Creek State Park, featuring lake loops, stream crossings and muddy singletrack. Family friendly for ages 8 to 100, organized by volunteers with proceeds b..

UltraTrax Wisp at Wisp Resort near Deep Creek Lake on April 11, 2026 invites walkers, hikers, ruckers and runners to tackle scenic 7 mile loops with punchy climbs and ridge top views. Choose 1 to 4 loops, try a weighted ruck, and support th..

Run the flat, fast Yough River Trail at the Boston Trail Half Marathon and 5K in Elizabeth Township, PA on April 18, 2026. Enjoy medals, pacers in the half, and a family friendly 5K while supporting local trail upkeep.

Experience a nighttime trail run at Coopers Rock State Forest on April 25 with scenic overlooks and rugged singletrack in a 50 km ultra or a 21 km half marathon. Bring a headlamp and backup for big climbs and unforgettable views.

Run scenic trails at Third Winchester Battlefield with 5k, 10k and half marathon loops over light gravel and dirt. Chip timed with medals, technical shirts, on course aid and a virtual option, plus series points for racers.

Run the rugged 5.25 mile loop at Valley Falls State Park on May 9 in 6 or 12 hour formats, with rocky climbs, stream crossings and scenic waterfall views. A challenging trail race that benefits the Innocent Lives Foundation.

Tackle the Massanutten Mountain Trails 100, a 100 mile ultramarathon in Virginia's Shenandoah Valley with over 18,000 feet of climbing on rocky, rugged trails. You get 36 hours, live volunteer timing, well stocked aid and required GPS track..

Join the Path of the Flood on May 23, 2026 with 5K, 8 Mile, or 14 Mile courses that pass through the luminary lit Staple Bend Tunnel and scenic trails, finishing at Peoples Natural Gas Park. Proceeds benefit Cambria County trails.

The Old Dominion is a 100 mile loop through the Massanutten Mountains, offering rugged climbs and mixed road and trail terrain. Part of the Grand Slam of Ultrarunning, it runs June 6, 2026 with a 24 hour silver buckle cutoff.

Experience the rugged beauty of Laurel Ridge State Park at the Laurel Highlands Ultra in Ohiopyle. Run point to point along the Laurel Highlands Hiking Trail with 70.5 mile and 50K solo and relay options for adventurous runners.

Experience Highlands Sky 40M, a rugged 40 mile ultramarathon through West Virginia's Monongahela National Forest and dramatic Dolly Sods. Based at Canaan Valley in mid June, expect wild mountain trails and unforgettable views.

Join Hell Hath No Hurry at Settler's Cabin Park on June 27, 2026 for scenic trail races from 10K to a 50 mile epic. Every finisher gets custom technical socks and a handcrafted award, with podium prizes for top men and women.