You really haven't been cycling until you've done so in the Bluegrass, my friends say. I have to agree, as my rides elsewhere have never measured up to the sheer beauty I've experienced right here at home.
The best way to take it all in is--by far--the Bluegrass Cycling Club's annual Horsey Hundred, held on Memorial Day weekend. Rides leave from Georgetown (after Buddy from Keeneland racetrack bugles the "Call to Post") and range from 25 miles to the century at 103 on Saturday. Some routes allow you to decide your distance once you see how you're feeling. The surroundings are absolutely stunning, from the stone fences and stately horse farms to the wandering creeks and exposed-limestone-studded hillsides. After refueling Saturday afternoon in Georgetown, Ky., with burgers and barbecue, volunteers host a festival in quaint Midway on Saturday night.
Last year I dined with friends al fresco at Heirloom, my favorite Midway restaurant, prior to sauntering down to the festival (make a dinner reservation, though). Savor the beef tenderloin and purple potatoes.
Sunday the BCC offers a metric century (and also shorter rides), allowing a variety of vistas for your enjoyment in Bourbon County.
The scenery and well-stocked rest stops, plus the hundreds of friendly volunteers (and thousands of eager participants), make this a bucket list item for any cyclist. Wear a jersey that represents your region/hobbies/club/personality (or purchase a commemorative jersey) and pedal away!