Scenic Drive/Ride for Bourbon, Bicycle, or Horse Racing Enthusiasts
This vista of Diamond A Thoroughbred Farm is along one of my favorite cycling routes in Woodford County. The scenic stretch of Steele Road is part of the Horsey Hundred route, an annual 100-mile cycling century that cyclists nationwide attend Memorial Day weekend (the three-day event boasts routes from 25 to 103 miles in length).
Steele also leads down to McCracken Pike, to my favorite bourbon distillery, Woodford Reserve. Staff members there are passionate about the spirit and give a fantastic tour--you feel like you're witnessing production of something small-batch, special.
The best times to visit this region are April and October, although those will also be the busiest times for distilleries and restaurants. Keeneland's three-week race meets commence during these months, and a day at the races is a can't miss. This is probably one of the classiest, most beautiful tracks stateside. Woodford offers special gourmet dinners "on the porch" by reservation during these meets.
Horse Farm tours are also a good idea while you're here, but one or two will suffice unless you're a die-hard Thoroughbred racing fan. (Three Chimneys is probably my favorite--call ahead.)
I recommend getting lost (on purpose) along these small farm roads in Woodford County during photographers' "magic hour" in the evening. If you head in the general direction of Frankfort, KY, you'll wind past abandoned distilleries and warehouses, peeking out from behind curtains of ivy that have overtaken them.