1. Kentucky Bourbon Trail | Lexington, KY


What is it? A ride through Kentucky’s famous bluegrass hills, stopping at distilleries along the way.
Why go? You’ll see country roads lined with golden trees, historic bourbon distilleries and thoroughbred horse farms by biking along the Kentucky Bourbon Trail. Build your own bourbon trail by jumping on wherever you like, but one place to start is Lexington, home to more than 450 historic horse farms and 17 of the state’s biggest distilleries. Some distilleries are close to each other, and some can be 100 miles apart, which means you can choose to bike the trail for a day—or a month. This popular trail started with just seven distilleries in 1999 and now has more than 60. Today, 2.5 million visitors a year engage in some part of the trail.
Time Out tip: Distilleries often book 6 ti 12 weeks out, so jump on it now!