Driving Tourism to Trail Towns

OUTdrive Episode 94 with Kim Henderson

OUTdrive Episode 94 with Kim Henderson

The Katy Trail State Park is the longest developed rail-trail in the country, spanning 240 miles between Clinton and Machens with 26 trailheads and four fully restored railroad depots along the way. Whether you are a bicyclist, walker, equestrian, nature lover or history buff, the trail offers opportunities for recreation, a place to enjoy nature and an avenue to discover the past. After spending nearly her whole adult life around the Katy Trail, Kim Henderson saw an opportunity to bring more tourism to the small trail town of Windsor by building a cabin rental business.

Kim is the owner and operator of Kim’s Cabins. Located right on the Katy Trail, her business offers a tranquil escape with several recreational options for visitors. Before owning her own business, Kim spent several years at First Community Bank, now Equity Bank. She also served as the City Administrator of the City of Windsor until 2018 when she took her rental business full time. Kim gets to experience farm life on a daily basis and has gained quite the social media following by sharing photos of nature and wildlife on her land.

Katy Trail State Park attracts people of all ages and interests. Tune in to hear how Kim’s Cabins put Windsor on the map as a must-stay destination for those making the state-wide trek on the trail or those just looking for a weekend getaway.


  • 2:50 – Kim’s background growing up in St. Charles, Missouri, moving to Wyoming to work in hospitality and then eventually settling in Windsor, Missouri
  • 4:55 – Kim shares what inspired her to start Kim’s Cabins and the need it fills for those traveling through Missouri on the trail
  • 8:30 – How people can get ahold of Kim, book her cabin and follow her on social media
  • 10:30 – Kim explains what it takes to run a rental business and how important it is for small business owners to make personal connections
  • 14:30 – Kim shares some of the skills she acquired working for the City and for the bank that has helped her when starting her own business
  • 16:45 – What Kim thinks some of the trail towns have to offer those who are wanting to book a “getaway”
  • 22:00 – Kim talks about the ways people find her online, the community sites that have the biggest impact and the importance of reviews
  • 25:00 – Kim tells Cliff about the resources that are available to those folks who would like to learn more about the Katy Trail or Missouri State Parks
  • 26:40 – Kim shares what types of media she uses and how social media has been so important to her as a consumer and business owner
  • 28:10 – Kim shares what rural America means to her and the impact of Midwest hospitality she sees just on the Katy Trail
  • 29:30 – Kim and Cliff discuss why more people are migrating to small town USA