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.

Start the year fresh with the Chill in the Hills 5k trail run or walk in Bridgeport on New Year's Day. Enjoy a scenic route, score a beanie if you register early, and support the local Humane Society with a donated item.

Ring in 2026 with a 5K or 1 mile family fun walk along the flat Panhandle Trail in Oakdale, PA. Enjoy age group awards, a pacer to help hit target times, and a commemorative mug for the first 150 registrants.

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.

Hit the trails at Canoe Creek State Park on April 11, 2026 for the Dirty Kiln Trail Races, with a roughly 10K short course and a hilly half marathon. Expect singletrack, stream crossings and mud while supporting local charities.

UltraTrax Wisp at Wisp Resort in McHenry MD on April 11, 2026 invites runners to tackle 7, 14, 21 or 28 mile loops over scenic ridgelines and ski runs with almost 2,000 ft of climbing. Aid, timing, finisher swag and a post race party await.

Run under the stars at Coopers Rock State Forest on April 25, 2026, choosing a challenging 50 km or half marathon through overlooks, boulders, and steep climbs. Field limited to 250 runners so secure your spot early.

Push your limits at the Valley Falls 6 and 12 Hour, a timed challenge on a scenic loop through rugged trails and waterfalls. Enjoy stocked aid stations, local artist shirts, and support for Innocent Lives Foundation.

Challenge yourself on the Massanutten Mountain Trails 100 Mile Run, a rugged trail ultramarathon in Virginia with more than 18,000 feet of climbing. Expect rocky singletrack, well stocked aid stations, and a 36 hour cutoff.

Tackle the legendary Old Dominion 100, a 100 mile cross country endurance run near Fort Valley, Virginia with a history dating to 1979. Expect rugged mixed terrain, volunteer support and a silver buckle for finishes under 24 hour.

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.

Challenge yourself on the scenic Promised Land Trail in Canaan Valley State Park near Davis WV on June 27, 2026 with a 5.9 mile loop or an 11.8 mile double loop. All finishers get a medal and McClumsy T shirt, plus post race snacks and beer..

Ironstone 100K is a rugged 100 km trail ultramarathon through the Allegheny wilds on July 11 and 12, 2026. Expect remote terrain, minimal aid stations and no pacers for a true self reliant test of endurance.

Join the Roaring Run Race to the Moon, a lively night 5k walk or run in Apollo, PA. Enjoy a flat out and back trail under the stars, just bring a light and celebrate a fun community evening.

Take on a 30K open water swim across Pittsburgh's three rivers, starting at Point State Park with full boat and kayak support. This annual late August event raises funds to help families cover infant cardiothoracic surgery costs.

Which event would you like summarized? Choose one: Green Mile Loop Challenge, North Ridge Nightmare Trail Race, Frozen Goat Challenge, or Winterfells Challenge.

Join the Newton River Festival 5k in West Newton for a scenic 5k run or walk along the Gap Trail to kick off the river festival. Stick around for food, crafts, live music and fireworks for a full day of fun.

Tackle the Export 100, a 104 mile out and back on scenic Westmoreland Heritage and West Penn trails in Export, Pennsylvania on October 3, 2026. All profits support the local trail community and pacers are allowed after mile 62.

Run scenic North Park trails, including sections of the Rachel Carson Trail, at the FAAP Fall Classic in Gibsonia on October 4 2026. Choose 20k 10k or 5k, earn handmade bamboo medals, enjoy a folk dance finale, and support an orphanage in t..