Trail Running calendar near McHenry 2026-2027

Event Overview Tour de Trails is a series of four winter trail runs held on Saturdays from December 2025 to March 2026. Each race is held at a different forest preserve or park in the Rockford, Illinois area. Participants can register for i..

The Fight for Air Stair Climb returns to Milwaukee's 411 East Wisconsin Center on March 21, 2026. Participants can choose to climb the 30-story building once, twice, or take on the Power Hour challenge. A virtual option is also available fo..

Conclude the winter series with a 10K trail race at the Hickory Knolls Discovery Center. Navigate dirt paths and limestone trails to earn your finisher medal and final pieces of the challenge series gear.

Race against the clock on a 2.25-mile alternating loop trail in Lowell Park. Choose the 8-hour 806, the 3-hour 314, or form a relay team. Finishers within the time limit earn unique apparel.

Join a long-standing Waukesha tradition featuring marathon and shorter distances plus new rucking categories. Support local parks while enjoying a professionally managed event on scenic city trails.

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

Experience a 4 mile trail run through the historic St James Farm in Warrenville. Enjoy a scenic single loop course featuring rolling terrain, limestone paths, and wooded trails with awards for multiple age categories.

Celebrate Earth Day on the trails at Veteran Acres park. Choose from a 50K, 15-mile, or 5-mile loop on scenic single-track. The event focuses on being landfill-free and offers awards for top finishers.

Run through the scenic rolling trails of the Morton Arboretum on a USATF certified 10K course. Enjoy a lively post race party with live music and refreshments while supporting vital tree conservation and research.

A whimsical trail run in Deer Grove Forest Preserve featuring four distances on a wide, non-technical looped course. The event, organized by CUSS Running, includes inclusive community initiatives. One aid station at the start/finish support..

Run or walk to support Anderson Humane at their largest fundraiser. Choose a timed 5K run or bring your dog for a 1.5-mile walk along the Batavia Riverwalk. The event includes awards, a lure course, and activities for animal lovers.

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

Experience the Three Ravines Course at Wolf Road Woods with distance options of 3.1 or 5.4 miles. This family friendly trail event features a mix of single track terrain and a post race celebration with craft brews.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

Experience the largest undeveloped nature preserve in Cook County on these wide horsetrail courses. Choose between a full marathon or a 10 mile run featuring significant elevation gains and a supportive two way traffic layout.

The Chicago Yeti 7/11 Hour Endurance Run is a timed trail event on a 4-mile loop through the Palos Preserves. Runners choose a 7 or 11-hour goal, fueled by a unique aid station with unconventional snacks. It's a cupless race focused on incl..

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

Navigate the single track routes and wooded hills of the Outback Trail at Imagination Glen. This event features a 12K race and a 3K kids run through shaded terrain with mud and water crossings.