4 running, walking, fun run, and other events in Middleton, Wisconsin
From big races to Saturday morning group runs—find running, walking, fun run, swimming, triathlon, and ultra events and connect with the local endurance sports community.
Middleton
4 events in Middleton-
Sat, May 09, 2026 at 10:00 AMSee full details
The Glowing Smiles 5K run/walk will begin and end at the Orchid Heights Park shelter in Middleton, WI. It is a loop around the Pheasant Branch Conservancy. The event begins with a free Kids fun dash at 9:45am, followed by the 5k run/walk at 10:00am.
Cost: $30 for runners and walkers over 15 years of age, $15 for kids 15 and under (no limit, must be accompanied by registered adult).
Please note: after April 19th we cannot guarantee a participant shirt or size.
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Sat, Aug 15, 2026 at 8:30 AMSee full details
Tri 4 Schools is a part of Active Youth Wisconsin, a nonprofit committed to empowering kids to be happy, healthy, and confident through movement. To support our mission, we donate 100% of youth entry fees to the participants' schools.
We offer 4 in-person course distances for this race. While there are recommended ages listed below, please select the course that best matches your child’s ability and interest, regardless of age. Note that the Long Course is only open to athletes age 7 and older. If your athlete uses a bike with training wheels, they must be registered for the Short Course. There is also an At-Home option for participants who are interested in a virtual option. We strive to make our events accessible for children of all abilities; please contact us if you would like to discuss any specific accommodations for your athlete.
Long Course (recommended ages 11-14): Swim 100 yards (4 lengths of the pool), Bike 4 miles, Run 1.2 miles
Medium Course (recommended ages 7-10): Swim 50 yards (2 lengths of the pool), Bike 2.1 miles, Run 0.7 mile
Intermediate Course (recommended ages 7-10): Swim 25 yards (1 length of the pool), Bike 2.1 miles, Run 0.7 mile
Short Course (recommended ages 3-6): Swim 25 yards (exits 0-depth side of pool), Bike 0.5 mile, Run 0.2 mile
At-Home: Complete your race wherever and whenever you like! Please follow all traffic rules and safety recommendations as you complete your race.
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Sat, Aug 22, 2026
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Sat, Aug 29, 2026 at 9:30 AMSee full details
Join us for the Middleton Good Neighbor Fest 5K Run/Walk on Saturday, August 29th at 9:30am. $35 for the run ($30 until June 9th), $30 for the walk ($25 until June 9th) and $20 for kids 12 and under. All proceeds benefit local service organizations around Middleton.
Early packet pick up will be held at Fleet Feet Madison, 8440 Old Sauk Road on Friday, August 28th from 4pm-6pm. You can also register or pick up your packet on August 29th from 8:15am-9:10am at Middleton High School, 2100 Bristol (on the corner of North and Middleton Street, near the south entrance of the high school.)
Thank you to our amazing Good Neighbor Sponsors! Lake Ridge Bank, Harbor Athletic Club, Willy Street Co-op, US Bank, Fleet Feet and Murphy Desmond, and we appreciate the Boy Scouts for volunteering at the 5K.
https://www.goodneighborfestival.com/
*The course is now back on some of the path!
https://www.mapmyrun.com/routes/view/6611950113/
*Register by August 9th, 2026 to guarantee your shirt size. More shirts will be ordered after the race to guarantee correct shirt size.