Trail Running calendar near Brookfield 2025-2026

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prai..

Colorama at Lapham Peak Colorama is an annual run and walk held at Lapham Peak State Forest in Delafield, WI. The 2025 event is listed as the 36th annual Colorama. Races use wide, well-groomed ski and hiking trails within the park. The even..

Event details The Trail Run At Indian Lake takes place on Saturday, October 4, 2025, at Indian Lake County Park in Cross Plains, WI (8183 State Highway 19). Registration for the 2025 race is open. Listed entry fees are shown as $30 or $20,..

The Milwaukee Beer Run 5k & .05k takes place in Glendale, Wisconsin, at the Bavarian Bierhaus. The event features a 5k Beer Run/Walk (3.1 miles) and a 54-yard .05k Beer Run/Walk, with a virtual option for remote participants. The course is..

Farmer Ken's Pumpkin Dash 5K takes place in Franksville, Wisconsin (53126). It is a 5K trail run along a grass/dirt path set beside corn and other farm fields, offering a scenic rural landscape. The course runs through agricultural surround..

Experience the scenic and fast Des Plaines River Trail in Lake County, IL with Half Marathon, Marathon, 50K or 50 Mile distances starting and finishing at Half Day Forest Preserve. Flat crushed gravel and brilliant fall color make it ideal..

Zachariah's Acres Fall Run, Walk & Roll is held in Oconomowoc, Wisconsin, on a scenic 125-acre private property featuring tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The event offers a 5K, a half marathon,..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event includes three distances: a 5-mile run, a 5-mile bike, and a final 5-mile run, with options for solo competition or 2- or 3-perso..

Race For Open Space is a West Bend, Wisconsin trail running event at Cedar Lakes Conservation Foundation's Fox Hill Nature Preserve. It offers a 5K trail run, a 10K trail run (two loops), a 1-mile trail walk, and a 5K for ages 18 & under. T..

The Over The Vines Wine Run/Walk is held at Over the Vines Vineyard & Wine Barn in Edgerton, Wisconsin. This event offers a 5K timed run, a 5K untimed walk, and a 2K untimed walk, all on a scenic trail featuring grass, gravel, and compacted..

Event details The event takes place on October 18, 2025 in Crystal Lake, IL. Distances offered: 10 mile - $69.00 5 mile - $47.00 Early bird pricing is available until July 30, 2025. Registration closes October 15, 2025 at 11:59 PM CT. Ent..

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and..

Howl-o-ween 5k – Schaumburg takes place in Rolling Meadows, IL at Busse Woods. This pet-friendly 5k run/walk follows a scenic, paved, flat out-and-back Busse Woods Trail and is timed by J3 Timing with live results. The event supports animal..

ERC John Hennelly Public Cross Country Races are held at Lovelace Park in Evanston, IL. The event features a three-lap, 3.5-mile cross-country course that weaves hills, open fields and varied terrain, offering a challenging run for individu..

Elver Park Trail Run is held at Elver Park in Madison, WI. The event features 10K, 5K Run/Walk, and a free 1K Kids Fun Run led by a friendly animal. All races begin and end behind the Main Shelter; the 5K uses the western half while the 10K..

Bristol Woods Trail Run takes place in Bristol, Wisconsin at Bristol Woods County Park, hosted at the Pringle Nature Center (9800 160th Ave). The event offers a 5K Trail Run and a 2 Mile Walk, plus junior versions for participants 18 and un..

Warrior 5K & 8K...Through The Park is a fall trail running event held at Greenfield Park in West Allis, Wisconsin. The weekend offers a 5K Run, 8K Trail Run, a 2.25 Mile Walk, and team options for the 5K and 8K, with cross-country-style sco..

The Fast Track Cross Country Open is a 3.05-mile race held in Schaumburg, Illinois, on the MacNider cross country course near Hoover Elementary School. Scheduled for November 9, 2025, it features separate women's and men's races open to all..

PROMixed XC Relay is held at Mitchell Park in Brookfield, Wisconsin (19900 River Road). The mixed-gender relay features four runners per team in the order male, female, male, female, with each athlete running 3000 meters. The event, backed..

Event details The Big Timber XC Challenge takes place Sunday, November 9, 2025 at Camp Big Timber, Big Timber Road at Tyrrell Road, Elgin, Illinois. Distances offered: 3 miles - one loop of the perimeter trail 5 miles - two loops of the pe..