Welcome to the Trail EAffect Podcast
Nov. 3, 2026

WinMan Trails with Operations Director Isaac Cowart | 216

WinMan Trails with Operations Director Isaac Cowart | 216
WinMan Trails with Operations Director Isaac Cowart | 216
Trail EAffect
WinMan Trails with Operations Director Isaac Cowart | 216

For Episode 216, we're joined by Isaac Cowart, Operations Director of WinMan Trails located in Northern Wisconsin. This is easily one of my top 10 conversations I've had the opportunity to host on Trail EAffect. Isaac brings a wealth of knowledge and experience to this conversation. We cover everything from trail planning and construction to staffing, maintenance, and what it takes to operate a successful nonprofit trail organization. There is a lot to take away from this episode, especially if you're involved with a trail organization or help manage trails that are open to the public.

Set List:

  • How Isaac found his way to Northern, Wisconsin
  • How Isaac got into mountain biking
  • The WinMan Story according to Isaac
  • A strategic plan was created
  • Hiring trail builders
  • The region where WinMan is located
  • How WinMan is contributing to the tourism economy
  • Bringing staff and trail builders in house
  • Quality over Quantity and Trail Maintenance
  • WinMan Basecamp, Camping, Cabins and Amenities
  • Events or lack thereof and why
  • Winter use and activities
  • Directional Trails and why WinMan is 100% one-way trails
  • Support trails when you can where you can, any trail system that you can
  • What Isaac looks for a trail community
  • Closing Comments

Trail EAffect Show Links:

WinMan Trails: https://winmantrails.com/

Show Support By:

KETL Mtn Apparel Affiliate Link: https://ketlmtn.com/josh

Trail One Components: https://trailone.bike/josh

Smith’s Bike Shop – 131 Years of Excellence: www.smithsbikes.com

Trail EAffect Podcast Website: www.traileaffectpodcast.com

Contact Josh at evolutiontrails@gmail.com

This Podcast has been edited and produced by Evolution Trail Services