Walking in a circle truly helped me move forward.
I drove past the grass field at the intersection of Colby Road and the Bypass for the better part of five years without paying it much more than a glance. Sure, the aging barn had that great aesthetic you see across Kentucky’s rolling hills, but I really didn’t give the Winchester Traveling Trail a thought.
But to really tell this story right, I need to loop back to 2020.
We were in the middle of a pandemic and, as I have shared before, I decided to change careers at a personal inflection point. I was at my lowest on the LYs that matter most in this world: physically, mentally, emotionally, spiritually, and financially.
They all fed one another, but my health was the greatest concern and my doctor really didn’t have any answers, despite my spending lots of money chasing symptoms. Insomnia, fatigue, weight gain, dizziness, and just an ever-present sense of blah were all part of the daily routine.
Until I decided it was time for a new doctor.
Everything changed with a single question. “Mike, what are you doing to treat your diabetes?” he asked. My response floored him: “Doc, I didn’t know I had diabetes!”
Well, there may have been some four-letter words involved, too.
With an A1c number of 10.8, nearly double the normal range, the problem screamed at him. Why was this not identified before? I still don’t have a good answer for that.
What I did know was diet and exercise were going to be key to turning things around. The gym doesn’t do much for me. Our treadmill was an expensive clothes rack. I love to hike but a 30-to-40-minute drive to trails wasn’t feasible.
That brings us full circle back to the Winchester Traveling Trail. It may sound hyperbolic, but I truly believe that nearly-one-mile patch of grass saved my life.
I saw that field with new eyes.
Being two minutes from my house made it very accessible. I challenged myself to walk five miles a day. I enjoyed the elevation changes and lighter impact than walking on concrete. The wide-cut grass path, the wildlife, the old tree at its center, and the aging barn were all part of the charm I was blind to before.
A year and a half later, I feel better than I have in at least a decade. I still try to make it to the field at least a few times a week.
Now, I can’t wait to see the trail become the best version of itself, too.
The Greater Clark Foundation owns the property and does an amazing job of maintaining it. Rumor has it some exciting things are on the horizon! So, I will offer my two cents (likely worth even less than that!) on what those could include.
The benches are great, but a couple of picnic tables would provide a great place for family picnics. Could some trees be planted that would provide shade for the next generation? Is there a way to expand the path into the forested area at the eastern and southern edges?
My understanding is the signage will soon be replaced. But the big news, and perhaps most exciting, is I hear the new barn is about to get a paint job.
The old structure was scary, looking like the perfect set for a horror movie. There were issues with keeping people out of it and I even called the Winchester Police Department once to let them know someone had broken open a door.
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Those warts aside, it also had a giant mural proclaiming it the Winchester Traveling Trail! The painted quilt pattern you see on barns throughout rural Kentucky felt like home.
I have no idea what the new structure’s extreme makeover will look like but drawing on the look of the past for this barn’s future would be exciting to see.
Hopefully, more people will start to take advantage of this great natural beauty we have here.
Study after study has shown that green space is integral to a community’s overall health. Winchester is blessed to have a resource like this that offers a welcome alternative to gym memberships or school tracks.
The trail may be a giant circle, but it could definitely go somewhere exciting in the future.

