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Trail Running Calendar near Libertyville 2026-2027

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Explore the top trail runs near Libertyville for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
A trail event at Pringle Nature Center on November 7, 2026 offering a 5K run and 2 mile walk with fees supporting environmental education.
Trail running at Camp Big Timber on November 8, 2026 with 3 and 5 mile courses, a creek crossing, kids run, awards, pancake breakfast and proceeds to local scouts.
A 3-mile cross country meet at the MacNider course in Schaumburg on November 8, 2026, with separate men's and women's races and an optional team competition.
A scenic 5K in Deer Grove on November 14, 2026 that welcomes runners, walkers and canicross teams while raising funds for a local scholarship.
Regional cross country championships in Kenosha, WI on Nov 28, 2026 with multiple grade specific 5K races and a youth 3K; top 10 advance to Brooks XC Nationals.
January 2027
Winter trail race in Crystal Lake, IL featuring a hilly single-track 10K loop and a 50K made of five laps, with aid stations, finisher medals, and age-group awards.
April 2027
Trail trail race in Crystal Lake on April 17, 2027 offering 50K, 15 mile and 5 mile options on a 5 mile loop with aid station and age group awards.
Multi-distance trail event at Deer Grove Forest Preserve near Palatine, IL featuring 50 Miler, 50K, 25K and 5.5 Miler on mostly wide, non-technical trails.
May 2027
Nighttime obstacle race in Pingree Grove, IL with multiple 5K heats and a 30K unlimited laps option, illuminated obstacles, live entertainment, and onsite parking.
June 2027
McHenry County Patriot Run on June 6, 2027 features a patriotic community gathering with a 5K, 10K and 1 Mile fun run at Three Oaks Recreation Center.
August 2027
A Scottish Highlander themed obstacle race in Pingree Grove on August 7, 2027 offering 50K, 15K, 5K, family 3K, a torch lit night run and a haunted 5K.
Community cross country event in Mount Prospect offering 1, 2 and 3 mile races to raise funds for Holiday Heroes, with professional timing and awards.
Mud run at Richardson Adventure Farm on August 28 and 29, 2027, offering 15K and 5K courses, Infinity laps, spectator passes, and finisher medals and shirts.
September 2027
A family friendly fundraiser on September 18, 2027 at Petrifying Springs Park with 1 mile and 2.25 mile routes and a virtual option supporting Rey de Reyes Ministry.
Timed trail event at Richard Bong State Park on September 25, 2027, offering 3, 6 and 12 hour options on repeated 0.97 mile loops with hourly challenges.
October 2027
Oct 9, 2027 trail races in Lake County IL offering 50 mile, 50K, marathon and half marathon on a flat crushed gravel out and back course; marathon is Boston qualifying.
Trail running event in Crystal Lake, IL with 5 and 10 mile single-track courses, race shirt, finisher medal, and a 3.5 hour cutoff.
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