Trail Running calendar near Lincolnshire 2026-2027

Take on scenic trails through Teason's Woods at Cap Sauers Holding Nature Preserve with marathon and 10 mile options on wide horse paths. Enjoy rolling hills, well stocked aid stations, limited parking and a unique wooden finisher medal.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 10 May 2026. You can run between 5 and 21 kilometers.

A trail event in Delafield, Wisconsin offering half marathon, 10K, 5K, ruck options and a Kiddos 1K; proceeds benefit Tall Pines Conservancy and courses use marked park trails.

The Trail Run Xtreme will take place in Portage on Sunday 17 May 2026. You can run 12 kilometers.

A chip timed 5k at Cooper's Hawk Winery in New Lenox on May 24, 2026, limited to 500 runners and walkers. Registration includes race swag and a wine pour while the event supports the New Lenox Food Pantry.

A 5 mile trail run at Stoney Run County Park on May 25, 2026, featuring flagged turns, an aid station just past mile three, possible mud and a pond crossing with a short detour option, and post race refreshments.

Free one day running festival in Crystal Lake celebrating local races, clubs, and brands. Pick a 4.3 or 6.8 mile social run, browse the expo, enter raffles, demo gear, and enjoy food, drinks and community fun.

A 5 kilometer run or walk in Joliet on June 6, 2026, starting and ending at Cemeno's, with proceeds benefiting the Pat Clark Cancer Foundation; registration includes a T shirt and finisher medal.

A multi-distance trail event near LaGrange, Wisconsin on June 13–14, 2026, featuring 100% trail courses and a lottery entry system. Distances range from 50K to 100 miles and the 100 mile finish in 30 hours qualifies for Western States.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 14 June 2026. You can run between 5 and 21 kilometers.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

A trail running event in Valparaiso that uses golf-style scoring across repeated three to four mile "holes". Options include 50K and 10M distances plus relays, with scores based on finishing windows and lowest cumulative strokes.

Celebrate the 45th Annual Brickyard Run on June 27, 2026 in Hobart, IN with a family 2K fun run plus timed 5K and 5 mile races along scenic streets and the Oak Savannah Trail. Collect the famous brick awards for top finishers.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 27 June 2026. You can run between 5 and 21 kilometers.

The Kishwauketoe Cross Country Run will take place in Williams Bay on Saturday 4 July 2026. You can run 5 kilometers.

Trail runs at Twin Creeks Farm in Valparaiso feature tree covered single track, switchbacks, bridge crossings and farmland views. Races include 18 mile, 9 mile and 4 mile looped courses with finisher awards and youth pricing.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 1 August 2026. You can run between 5 and 21 kilometers.

Run the Rails in Elburn, IL features a 1-mile fun run/walk plus 4- and 7-mile races starting and finishing at Prairie Park, with course views from the Anderson Road bridge and chip timing for the timed events.

A technical trail event at Franklin Creek State Natural Area near Franklin Grove, IL, offering 5K and 10K courses with multiple creek crossings, notable elevation changes, on-course water at key points, race shirts, and awards.