Crossroads Of Opportunity For Windsor With Rock Island Trail

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People come from all over the world to ride the 240 miles of the KATY Trail, the longest continuous rails-to-trails recreational trail in the United States.
When the next 144 miles of the Rock Island Trail is completed and is connected to the KATY trail at its eastern end, the loop will become the longest rails-to-trails route in the world.
Both the Rock Island Trail and the KATY Trail are state parks, and both go right through the town of Windsor.
Kim Henderson, owner of Kim’s Cabins in Windsor, gave an update of the development of the Rock Island Trail at the March 10 meeting of the Windsor Historical Society. Her message:
“Wake up, Missouri. Wake up, Windsor,” Kim said. “We’re unique. We have both trails here, handed to us.”
“Nobody else has this on the KATY or the next 144 miles of the Rock Island.”
As vice-president of the Friends of Missouri Rock Island State Park, Kim spoke last June at the official opening of the first 47-mile section of Rock Island Trail State Park, a recreational corridor for walking, biking and non-motorized transportation, which starts at Pleasant Hill and goes to Windsor, with trailheads in Medford, Chilhowee and Leeton. The ceremony was held in Windsor, where the KATY Trail passes over the Rock Island Trail on a bridge, near the Windsor High School.
The next 144 miles of the railroad trail corridor, is not yet developed or open to the public. But in 2022, Kim attended a signing ceremony in Eldon, where Missouri State Parks officially accepted ownership of the former Rock Island Line track bed that spans mid-Missouri, going through Henry County to Ionia and Cole Camp in Benton County, then Stover, Versailles and Barnett to Eldon, and crossing five more countries to Owensville, Gerald and Beaufort, south of Washington.
“We’re at one end of a 450-mile loop,” Kim said of Windsor.
Kim said Rock Island Trail supporters had hoped for a state grant to develop the recreational trail, but funding fell through. So the Rocky Island Trail is now progressing one section at time, Kim said, as towns along the trail get financing.
“Six communities have gotten grants,” Kim said. “The town of Gerald, south of Hermann, is expected to have the first mile of trail finished.”
Gerald used local funding and donations, she said.
To connect the Rock Island Trail to Kansas City on the west end, Jackson County purchased and created a paved bicycle path that starts at the Chiefs stadium and goes through Raytown and Lee’s Summit.
Raytown really benefited from the increased tourist traffic, Kim said.
“Crane Brewing suddenly became the place to be,” she said of the brewery at 6515 Railroad St. “Local cyclists come for day rides, and people fly into Kansas City with their bicycles, unpack them and ride the trail.”
There is one unfinished section between Lee’s Summit and Pleasant Hill, but from Lee’s Summit, the Jackson County section connects to the sports stadiums in Kansas City.
Cole Camp is two miles off of the route of the Rock Island Trail, Kim said, but the community has gotten a grant plus donated land to put up a trailhead. Once sections of the Rock Island Trail are developed through the communities, it will be a matter of connecting the dots, she said.
Kim said her cabins are already booked for half the year, and not all the visitors are cyclists. People stay at Kim’s Cabins who are in town for weddings, the birth of grandchildren and annual family reunions, Kim said. The cyclists say they enjoy the quiet, the farmland and the Amish.
The Rock Island Trail through Windsor now extends to Windsor’s Farmington Park, which has a fishing lake, a half-moon bridge and a disc-golf course. In Central Missouri, the route of the Rock Island Trail goes through three tunnels and over two bridges, the most impressive being the 1,700 foot long Gasconade Bridge over the Gasconade River.
One of Kim’s visits to trail sites along the Rock Island included experiencing what it was like to walk on the old bridge.
“I was very hesitant to walk out of on it,” she said. “I had to hold onto Ron’s hand,” referring to Ron Bentch, trail development coordinator.
Kim also got to go through one of the tunnels, and describes the features on the Rock Island Trail as “just amazing.” Unlike the KATY Railroad, the Rock Island Line shipped produce and products, connecting more than 20 small historic railroad towns in Central Missouri. Plans call for the recreational trail to turn north and connect with the KATY.
At the next meeting of the Windsor Historical Society, historian Glynna Morse will give a history of the Rock Island Railroad, which first arrived in Windsor 120 years ago. The train is gone, the coal is gone, and the shoe factory is gone, Kim said, but what Windsor has now is the trail and the economic opportunities to provide services for cyclists.
With bicycle tourism growing, people are seeing the potential of Windsor. Donavan and Kelly Thompson moved to Windsor and restored a shop front at 212 S. Main St., where they opened The Pour Poet, a coffee, tea, book and antiques shop. Donavan is now working on the space next door, which he is turning into the Restore It Shop, Kim said.
In another development, a couple opened a barbecue restaurant, with plans for a taproom.
Other Windsor Historical Society programs on the horizon: On May 11, Tom Colwell will give a program on Henry Avery, the first person of European ancestry to settle in Henry County. In June, Dorothy Warren will present a program on Windsor bowling alleys, particularly appropriate now that someone is starting to renovate Windsor Lanes.
In July, Bob Colvin, a Jefferson City photographer, will present “Back Roads of Missouri and Beyond.” The Windsor Shoe Factory annual reunion of employees and descendants is in August, starting with a luncheon at Windsor United Methodist Church.
The Rock Island Trail will not be completed quickly, Kim said, but it’s coming. When she first moved to Windsor, where she worked at a bank and then the city administrator, she watched the dotted line on the map of the planned trail for 15 years. She put up her first cabin 10 years ago near the bridge where the KATY Trail crosses over the Rock Island Trail. At that time, Windsor’s only lodging option was the motel, which could house 17 people.
Kim put up three more cabins and in 2018, quit her full-time job. The cabins are booked for half of this year, she said. Due to family situations, Windsor lost two other lodging options, Fitzgerald’s and the Porter House, but she’s hoping more people will see the opportunity.
“I want people to see the big picture,” Kim said. “We have a huge potential as the trail expands.”
Kim noted that visitors eat at local restaurants, and buy groceries and gas. Judy’s Kitchen and the Wagon Wheel are popular, and last Saturday, there wasn’t a vacant table at the Sidetrack Cafe, the train-themed restaurant at 800 W. Benton.
Kim thinks there’s room for more lodging options and restaurants offering different cuisines in Windsor. She sees promoting the trails as a team effort of Windsor residents and the residents of all the towns along the recreational trails.
“I’ve heard that 40,000 people have biked the KATY Trail,” she said. “I think there’s been more than that.”
The Windsor Historical Society meets on the second Saturday of the month. February through December, in the Research Center at the Windsor Museum, 214 W. Benton St. From Clinton, take Mo. Hwy. 52 E to Windsor and turn left at the four way stop/main intersection. Meetings are preceded by a light lunch at 12:15 p.m, followed by a short business meeting and a program at 1 p.m. Call Dennis Carter at 785-224-8956 for more information.
The Pour Poet is open Monday through Friday, 6 a.m. to 4 p.m.
To contact Kim’s Cabins, call 660-351-0905.