Trail Running calendar near Jackson 2026-2027

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

A community running event at Fort Atkinson High School featuring a 12K mixed terrain route, a 5K on neighborhood streets, and a 1 mile untimed walk/run, with overall and age group awards for the 5K and 12K.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

Regional cross country championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.

A dog-focused trail run at Lake Geneva Ziplines and Adventures offering one or two loops on winding singletrack. Canicross and dog friendly options are available, with podium awards reserved for dog-equipped finishers and a finisher gift fo..

Quiet Silence is a winter evening out-and-back trail event in Lake Mills, WI offering 16 and 31 mile distances on a flat crushed-limestone rails-to-trails course. Aid stations, drop bags, cupless aid, and mandatory safety lights are require..

A winter obstacle race at Lake Geneva Ziplines & Adventures on January 30, 2027 offering distances from a kids loop to a 20K Yeti Challenge; fun heats allow optional obstacles while a competitive division awards cash prizes. All in-person f..

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

Trail runs in Greenbush, Wisconsin along the Ice Age Trail offering 50K and 25K with transportation to the start, aid stations, and post run refreshments. The event is organized as a run rather than a race.

Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.

A trail event in Belleville, WI on May 29, 2027 offering 50 mile, 50K and half marathon options on flat, soft rail trails with trestles, scenic views and a quarter mile tunnel.

A timed long distance walking event at Alpine Valley, Elkhorn, WI on October 9, 2027 offering 7, 14, 21, and 28 mile loops, optional weighted vests, and a 10 hour finish limit.

Paws for a Cause in Denmark WI on October 16, 2027 offers canicross and solo trail run or walk options of 2.8, 5.6, and 8.4 miles, with proceeds benefiting Crisis Cafe.