3 running, walking, and cycling events in Sheboygan, Wisconsin

From big races to Saturday morning group runs—find running, walking, and cycling events and connect with the local endurance sports community.

• Team Maywood 2026 [runsignup.com]
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  Mon, May 04, 2026 at 5:30 PM

  Description

  This summer-long training program will help improve your group riding skills in a supportive environment. The program includes Monday evening rides starting from Maywood Environmental Park in Sheboygan, 5 weekend rides, and an end-of-season celebration ride. For full program information and ride calendar visit our website: GoMaywood.org

  Participants in Team Maywood must be 18 years old or older.

  Cycling

  3615 Mueller Road, Sheboygan, Wisconsin, 53083, United States
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• Sheboygan A's 5K with myTEAM TRIUMPH [runsignup.com]
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  Sun, May 17, 2026 at 8:00 AM

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  Race with myTEAM TRIUMPH at The 10th Annual Sheboygan A’s 5K Home Run/Walk, starting and ending at Wildwood Baseball Park in Sheboygan, on Sunday, May 17th. Register today as an ANGEL or a CAPTAIN....

  Race with myTEAM TRIUMPH at The 10th Annual Sheboygan A’s 5K Home Run/Walk, starting and ending at Wildwood Baseball Park in Sheboygan, on Sunday, May 17th. Register today as an ANGEL or a CAPTAIN.

  ANGELS: The ones who are able-bodied athletes and decide to run for inclusion! They guide the CAPTAIN to the finish line and help create special moments.

  Not a committed Angel? Apply Here

  CAPTAINS: The heart and soul and the reason we run! myTEAM TRIUMPH Captains are individuals with a disability of any kind.

  PHOTO CIRCLE: myTEAM TRIUMPH athletes, to capture our special memories from this race over the years join our Photo Circle. This can be found on the left-hand side. Upload your new race day photos from 2024 or reflect on past years.

  5k Run Walk

  Sheboygan, Wisconsin, 53082, United States
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• Sheboygan YMCA Freedom Run with myTEAM TRIUMPH [runsignup.com]
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  Sat, Jul 04, 2026 at 7:30 AM

  Description

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  Race with myTEAM TRIUMPH at the 2024 Sheboygan County YMCA 5 Mile Freedom Run/Walk event on July 4th! Register today as an ANGEL or a CAPTAIN.

  ANGELS: The ones who are able-bodied athletes and decide...

  Race with myTEAM TRIUMPH at the 2024 Sheboygan County YMCA 5 Mile Freedom Run/Walk event on July 4th! Register today as an ANGEL or a CAPTAIN.

  ANGELS: The ones who are able-bodied athletes and decide to run for inclusion! They guide the CAPTAIN to the finish line and help create special moments.

  Not a committed Angel? Apply Here

  CAPTAINS: The heart and soul and the reason we run! myTEAM TRIUMPH Captains are individuals with a disability of any kind.

  PHOTO CIRCLE: myTEAM TRIUMPH athletes, to capture our special memories from this race over the years join our Photo Circle. This can be found on the left-hand side. Upload your new race day photos or reflect on past years.

  5 Miles Run Walk

  812 Broughton Drive, Sheboygan, Wisconsin, 53081, United States
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