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Trail Running Calendar near Lincolnshire 2026-2027

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Explore the top trail runs near Lincolnshire for 2026-2027! We've gathered 36 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
A continuous loop trail race at Deer Grove East Forest Preserve in Palatine IL offering 40 or 50 mile distances on a 3.1 mile loop with full aid support.
Loop-format trail event at Deer Grove East Forest Preserve offering distances from 5K to 50K plus continuous 40 mile and 50 mile challenges with central aid.
A retro 5K cross-country race by Fox River Trail Runners at Settler's Hill in Geneva. Entry fees are $10 for members and $12 for non-members, and proceeds support the course's preservation.
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.
Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.
Loop based endurance event at Busse Woods on August 15, 2026 offering repeated 3.1 mile laps over smooth crushed limestone and packed gravel. Distances range from 5K to 50K with a central aid station and open loop format.
Continuous 3.1 mile loop at Busse Woods near Elk Grove, IL offering 40 and 50 mile options with a fully stocked aid station every lap and a 12 hour cutoff. Runs alongside The Next Loop series but is scored separately.
Trail races at Paul Douglas Preserve offering approximate 4, 9.5 and 13 mile single-track courses as part of the Dick Pond Athletics Darn Tough Trail Race Series.
A mud obstacle event on August 29, 2026 at Richardson Adventure Farm offering 5K, 15K, timed Infinity laps, Mudder Village, and finisher rewards.
Loop based trail event at Half Day Forest Preserve where runners repeat a 3.1 mile loop, stop after any loop with no penalty, and receive official timing for each completed loop for combined results.
A 6 km cross-country race at Lovelace Park in Evanston with scholastic races, team and individual entries, race shirts, awards, and a post-race gathering with food.
September 2026
A community run at Woodland Middle School in Gurnee on September 11, 2026, offering a 5K, 1 Mile, and a shirt only option. Proceeds support the Woodland PTA and confidential financial assistance for fees is available.
A timed urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.
A community fundraiser in Geneva with a 2.5 mile Lightning Run, a 1 mile kids race, and a Mini Road Race Rally for ages 3 to 8. Proceeds support the Geneva Park District Scholarship Fund.
In-person and virtual 5K, 10K and half marathon at Moraine Hills State Park with marked trails, water stations, and proceeds supporting park programs.
Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.
Timed 6 and 12 hour events on a 2 mile lakefront loop in Evanston with two aid stations, public water fountains, nearby parking, and a nonalcoholic finish beverage and finisher award.
A 30 minute run or walk up Mt. Hoy in Blackwell Forest Preserve, Warrenville IL, with proceeds funding two years of housing through Bridge Communities.
October 2026
Trail races on the flat, crushed gravel Des Plaines River Trail in Lake County offering Half Marathon, Marathon, 50K and 50 Mile distances.
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