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500 East Benton, Windsor, MO  |  owner@surlevelo.com  | 573.575.8117

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  • Crystal Monteleone

"Windsor is Amazing"

Updated: Jul 2, 2018

Those 3 little words set us off on an adventure

Windsor Trail head

Adam and I have worked in corporate jobs for some time and we had always dreamed about a life outside of the daily desk grind. One summer, during a 3-day ride on the Katy, we visited a B&B in Rocheport. You may know it, The Katy Trail B&B. Well, we loved our stay and had the opportunity to meet the owner, Brett Dufur. As we chatted with him and his partner while they freshened up the house, the spark was lit, could we run a B&B? We love to meet people. We love bikes. We love to make a home and entertain. Sure why not!


But as often happens with great big ideas...life got in the way and a year went by, and we had done nothing with that spark. Until one night, Adam was gone traveling, I had had a rough couple days at work and we were texting our goodnights. "Baby let's open a B&B". Adam quickly got excited..."Are you serious?" Like in that, Don't play with my emotions kind of way. "Yeah!"


From there we started researching towns along the Katy and the progress on the Rock Island was just getting momentum. Hmm, Where does the Rock Island and Katy Trail cross? It turns out that they cross in Windsor, MO, which was about 1.5 hr drive from Kansas City. Not too bad. Not 1 trail, but 2 in one town?!? Could this be the place? More Googling, more research. Weeks later we float this idea to some friends over a home cooked meal of lamb lollipops that were to die for. Johnny, a close friend, quickly responded with "I'd invest in that!" The universe was giving us another nudge. Come on guys, you don't know unless you try, give it a go!


And then we did nothing for another year. Until that same friend, Johnny asked us one night while we were partaking around a fire pit "Hey, what's happening with the B&B idea?" We had done nothing, why was that? What was holding us back? Nothing really. I got on Realtor.com the next day and started looking at properties for sale. There were some viable options. But we had never even been to Windsor. We knew nothing about the town other than what is on the web. We needed to make a trip and feel it out. Could we open a business and potentially live there? Was is a small sleepy town, or was it run down and abandoned as many small towns along retired rail lines had become?


In May of 2017, we took a weekend spur of the moment trip to Windsor to get a look. We decided to stay overnight so we could fully experience the town and ride the trail. We booked a cabin at Kim's Cabins and stayed the night. In the morning, we drove around town, we rode the trail and we grabbed some lunch. At Raymond's, a local diner, we had the opportunity to meet 2 cyclists from Ohio. They were riding the whole trail on vacation, what an adventure. We admired each other's bikes and went on our merry way. Adam and I did another circuitous bike around town and headed back to the trailhead all while contemplating. Is this the right move? Should we really do this? While loading our bike's on the car we noticed the same women we met earlier looking at the map at the trailhead and talking about how cute the town was while 2 teenagers with Windsor High School shirts on were crossing the trail on the way to Casey's General Store. One of them called back to the ladies "Windsors Amazing!" We heard the exchange looked at each other and smiled. "Did you hear that!" "Yep!". And the rest is history...we met a realtor the next weekend and put an offer in on a house the following week.


#windsorisamazing #katytrail #rockislandtrail #windsormo

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