Trail Running calendar near Libertyville 2026-2027

An annual June endurance trail event featuring 100 mile, 100k, 50k and 38 mile options on mainly Ice Age Trail terrain. Entry for 2026 is by lottery with an ordered waitlist and early invites for rollovers and volunteers.

Experience an authentic cross country race on a purpose built grass course in Geneva Illinois. Run as an individual or part of a team on this wide professional grade venue featuring rolling terrain and a classic atmosphere.

A trail running event on June 20, 2026, near Rice Lake in Whitewater, Wisconsin, using an out and back section of the Ice Age Trail. Routes range from 10K to 50K and include varied footing from smooth to technical.

A staged trail race where runners complete scheduled 3–4 mile Holes and aim for the lowest cumulative stroke score. Distances include a nine-Hole 50K and a three-Hole 10-mile option at Creekside Trails in Valparaiso.

A multi distance event at Hobart Middle School with a road and Oak Savannah Trail out and back route, computerized bib timing, and trademark brick awards across many age divisions.

Trail races at Wolf Road Woods on June 27, 2026 offer three loop choices covering 3, 6 and 9 miles with varied off-road surfaces, tiered registration fees and post-race refreshments and awards.

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

A 5K trail event at North Lake Park in Stevensville MI that raises funds for Alzheimer’s causes. The event is not timed and awards prizes to the three participants who catch the most deer flies using Tred Not Deerfly patches.

A prairie run and walk at Lapham Peak State Forest on July 11, 2026, using grass hiking and mountain bike trails. The event raises funds for prairie management and includes shirts for the first 100 participants and awards for winners.

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

H-F Beast Obstacle Course Dash in Homewood, IL on July 12, 2026 features two age categories with obstacle runs. The event awards finisher medals and t shirts and includes an optional prep course in June.

Midwest trail races at Creekside Trails in Valparaiso, IN offering 4, 9, and 18 mile options over single-track, switchbacks and creek crossings. Aid stations, a cupless format, post race meal and custom finisher awards are provided.

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

A continuous loop 40 or 50 mile trail race at Deer Grove East Forest Preserve in Palatine, IL. Runners repeat a 3.1 mile loop with a fully stocked aid station each lap and a 12 hour time limit.

Loop-based trail event at Deer Grove East Forest Preserve in Palatine IL offering distances from 5K up to 50K. Each lap returns to a central start area with a fully stocked aid station amid prairie, wetlands, and woods.

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

A Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

A loop-based trail event at Busse Woods where runners complete hourly 5K loops; each loop is timed and combined for official results, and participants decide whether to continue after each loop.

A continuous 40 or 50 mile loop race at Busse Woods on a 3.1 mile (5K) trail loop with fully stocked aid each lap and a 12 hour time limit. Personal supplies, crew zones, pacers, and on site medical staff support runners.

Run the Rails in Elburn, Illinois on August 22, 2026 offers a 1 mile fun run plus 4 mile and 7 mile courses that begin and end at Prairie Park. Courses cross the Union Pacific West rail line and benefit the Elburn Parks Commission.