Trail Running calendar near Freeport 2025-2026

Take on a rugged 20 mile loop in the Mines of Spain Recreation Area, Dubuque, Iowa on October 17, 2025, choosing either 100 mile or 100K distances. Expect steep technical single track, prairie sections and sweeping Mississippi River views.

Saw Wee Kee - Fall Trail Run is held at Saw Wee Kee Park, Sundown Lane, Yorkville, Illinois. The event is the Fall Trail Run segment of a four-race series; each race features a different course and medal piece, and completing all four earns..

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..

Join the Jaimie Cox Memorial Run in Roscoe on Saturday October 18 2025 for a scenic nature course from Roscoe Middle School with 5K run and 2 mile walk options. Proceeds benefit the Jaimie Cox Memorial Scholarship.

Black Hawk Ridge Trail Run is a trail-running event held in Mazomanie, Wisconsin, at the Black Hawk Unit of the Lower Wisconsin State Riverway. The race offers two distances, 8K and 16K, inviting runners of varied experience to tackle woodl..

Among the Trees on Oct 25 in Dousman WI invites trail runners to tackle 50k or 100k routes on Scuppernong and Ice Age Trail loops. Finishers get to brand a wooden medal with optional finish time for a memorable keepsake.

Energetic community races at the Momemtum Fall Classic in Janesville on October 25, 2025. Choose a 1 mile or a scenic three loop 5k on Optimist Community Park trails with proceeds supporting Momentum Track and Cross Country Club.

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..

Event The Miner 49er endurance runs take place on Saturday, November 8, 2025, in Dubuque, Iowa at the Mines of Spain area (8991 Bellevue Heights Rd). Distances offered: 25K 50K Registration closes on October 31, 2025. Race registration fe..

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..

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or..

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

Event overview The Guv'nor Frozen 50 takes place on December 6, 2025 at Governor Dodge State Park, Twin Valley Picnic Area, Dodgeville, WI. Distances offered are: 50K 25K 15K Parking requires a park pass; self-service kiosks are available..

Conquer winter trails at the Frozen Gnome in Crystal Lake on January 10, 2026, a technical single track 10K loop repeated for the 50K or tackled in relays. Expect triple black diamond terrain, a Gnome Depot aid station, and a finisher medal..

Event overview The 50K MASHUP SLAM is a series of trail races in the Midwest based on the 50K distance. The series includes multiple events across the year, begins with the Frozen Gnome 50K in January and concludes in November with the Mine..

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second..

Take on the Fox Valley Winter Challenge, a three race trail series across Batavia, Aurora, and St Charles this winter. Choose a 5K, 8K or 10K or grab the full series and earn gear from a hat to a sweatshirt as you run scenic forest preserve..

The Frozen Assets 5K Run/Walk is a unique winter event held in Madison, Wisconsin, where participants run or walk entirely on the frozen surface of Lake Mendota. The 5K course offers scenic views of downtown Madison and the University of Wi..