Century Rides in Kentucky
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Kentucky.
Cycling in Kentucky: Terrain & Route Overview
Cycling through the Commonwealth of Kentucky is an idyllic sensory experience, featuring pristine wooden fences lining manicured Thoroughbred horse farms, historic stone bourbon distilleries, and steep, forested hollows. The Bluegrass region around Lexington and Louisville delivers rolling, rhythmic terrain with smooth pavement and low traffic, while the eastern section of the state climbs into the rugged Cumberland Plateau and Appalachian foothills for serious vertical gain. Century events like the Bourbon Country Burn and Red River Gorge tours combine world-class road cycling with rich cultural heritage. Spring and autumn offer ideal temperatures and radiant foliage. With welcoming southern hospitality, historic town squares, and scenic country lanes, Kentucky is an unforgettable century cycling destination.
Terrain Characteristics: Bluegrass horse country rolling pastures, bourbon trail corridors, and Appalachian mountain foothills.
Riding Season & Weather: April through June & September through November.
📍 Kentucky Century Rides Map
10 Plotted EventsBike MS: Bluegrass Bourbon Ride
JuneJoin us on a one-day loop ride in the heart of bourbon country, taking in the beautiful rolling hills and countryside of Kentucky.
Bike to Beat Cancer 2026
SeptemberJoin the community and help save lives through the Norton Cancer Institute and Norton Children’s Cancer Institute, affiliated with the University of Louisville School of Medicine. The funds raised will help with prevention and early detection initiatives, advanced treatments, survivorship programs, and clinical research.
Bourbon Country Burn
SeptemberA three-day, fully-supported bicycle tour of the bourbon distilleries and Thoroughbred horse farms of Kentucky.
Cave Country Caper
AugustRolling routes past sinkholes, karst topography, and rural roads surrounding Mammoth Cave country.
Horsey Hundred
MayThe Horsey Hundred is a premier cycling event in Kentucky that offers five route choices, ranging from 26 to 103 miles, through the beautiful Bluegrass Region, featuring horse farms, stone fences, rivers, and historic towns.
Limestone Cycling Tour
SeptemberThe Century, the Metric Century, the 40-mile, and the 25-mile courses are each appropriate for a different level of rider.
Limestone Cycling Tour 2026
SeptemberJoin Limestone Cycling League and Maysville Rotary for a scenic ride through the countryside.
Old Kentucky Home Bicycle Tour
AugustExperience a Kentucky Summer and choose the best route for you and your group. This ride will feature three distance options: 62.1 mile (100 K), 40 mile or 20-mile all riding through scenic rolling hills of Oldham County.
PNC Tour de Lou
AprilThe PNC Tour de Lou is a unique way to explore Louisville on two wheels while passing through some of the city's scenic parks, neighborhoods, and historic sites with cyclists from all across the country.
Redbud Ride
AprilChoose from 4 beautiful routes, including a scenic metric century and a challenging 100-mile route, and enjoy a fun-filled day of music, food, and local shopping in downtown London.