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
9 Plotted EventsBike MS: Bluegrass Bourbon Ride
📅 Jun 13, 2026Take in the beautiful rolling hills and countryside of the Bluegrass State as you join a community of riders dedicated to changing the world for people affected by multiple sclerosis.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Jun 13, 2026 |
| Starting Venue | My Old Kentucky Home State Park |
| Location | Bardstown, KY, KY |
| GPS Coordinates | 37.80835, -85.461343 (Google Maps ↗) |
| Organizer | National MS Society ↗ |
| Entry Fee | $300 |
| Registration | Direct Registration Link ↗ |
Bourbon Country Burn
📅 Sep 25 – 27, 2026A three-day, fully-supported bicycle tour of the bourbon distilleries and Thoroughbred horse farms of Kentucky.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Sep 25 – 27, 2026 |
| End Date | 2026-09-27 |
| Starting Venue | Kentucky Horse Park |
| Location | Kentucky Horse Park, KY |
| GPS Coordinates | 38.155, -84.5177 (Google Maps ↗) |
| Organizer | Bourbon Country Burn Organizing Committee ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Horsey Hundred
📅 May 22 – 24, 2026The Horsey Hundred features five route choices ranging from 26 miles to the iconic Century (103 miles) through the Bluegrass region, with beautiful scenery, horse farms, stone fences, rivers, streams, lush pastures, historic towns, and bourbon distilleries.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map (2) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 May 22 – 24, 2026 |
| RWGPS Telemetry | Interactive Route Map (2) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| End Date | 2026-05-24 |
| Starting Venue | Charles Brooking Park |
| Street Address | 1080 Cincinnati Rd |
| Location | Charles Brooking Park, Georgetown, KY, KY 40324 |
| GPS Coordinates | 38.211712, -84.556179 (Google Maps ↗) |
| Organizer | Horsey Hundred & Bluegrass Cycling Club ↗ |
| Entry Fee | Early Bird Price SOLD OUT, Snooze Button Rate SOLD OUT, Procrastinator’s Special SOLD OUT, Sunday Only Ride Ticket $50 |
| Registration | Direct Registration Link ↗ |
Limestone Cycling Tour 2027
📅 Sep 11, 2027Follow this link to learn more about sign in and things to do while attending the Limestone Cycling Tour. https://limestonecyclingtour.com/while-you-are-at-lct/
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Sep 11, 2027 |
| Street Address | 150 Limestone Street, Maysville, KY |
| Location | Maysville, KY 41056 |
| GPS Coordinates | 38.647278, -83.762445 (Google Maps ↗) |
| Organizer | Limestone Cycling League and Maysville Rotary ↗ |
| Entry Fee | $55 - $80 |
| Registration | Direct Registration Link ↗ |
Old Kentucky Home Bicycle Tour
📅 Aug 08, 2026Experience a Kentucky Summer and choose the best route for you and your group. This ride will feature three distance options, a 62.1 mile (100 K), 40 mile or 20-mile all riding through scenic rolling hills of Oldham County.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Aug 08, 2026 |
| Starting Venue | 3rd Turn Oldham Gardens |
| Street Address | 6300 Old Lagrange Rd |
| Location | 3rd Turn Oldham Garden, 6300 Old Lagrange Rd, Crestwood, KY 40014, KY 40014 |
| GPS Coordinates | 37.839333, -84.270018 (Google Maps ↗) |
| Organizer | Louisville Bicycle Club ↗ |
| Organizer Contact | [email protected] |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
PNC Tour de Lou
📅 Apr 11, 2027A 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.
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Apr 11, 2027 |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| Starting Venue | Big Four Lawn |
| Location | Big Four Lawn, KY |
| GPS Coordinates | 38.2612, -85.7424 (Google Maps ↗) |
| Organizer | Kentucky Derby Festival ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Red Fondo
📅 May 08, 2027Welcome to the Red Fondo. We'd love for you to join us in this beautiful region of the Bluegrass State for our event. See Q&A below for more info. What kind of event is this? This is a Gran Fondo with all paved roads. See the Red Fondo Instagram for more details of what the course looks like. It will be mass start group event. Results based on finish line placing. First person across the line wins and so on. What...
⚡ Event Details & Specifications ›
| Dataset Population | 2027 Forward Calendar |
| Qualified Distances | ⏱️ Metric Century (62 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 May 08, 2027 |
| Street Address | 5099 Campton Rd |
| Location | Stanton, KY 40380 |
| GPS Coordinates | 37.831849, -83.783769 (Google Maps ↗) |
| Organizer | True Grit Cycling ↗ |
| Entry Fee | $75 |
| Registration | Direct Registration Link ↗ |
RedBud Ride
📅 Apr 18, 2026 (7:00 AM – 5:30 PM)A fun-filled day of music, food & local shopping will be available for spectators at the London-Laurel County Farmer's Market. Downtown London offers many retail & food/beverage options a short walk from the Market.
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | 🏔️ Imperial Century (100 mi)⏱️ Metric Century (62 mi)🗺️ RWGPS Map |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Apr 18, 2026 (7:00 AM – 5:30 PM) |
| RWGPS Telemetry | Interactive Route Map (1) → • Send to Wahoo/Garmin ↗ • GPX ⬇ • TCX ⬇ |
| End Date | 2026-04-18T17:30:00 |
| Starting Venue | London-Laurel County Farmer's Market |
| Location | London-Laurel County Farmer's Market, KY |
| GPS Coordinates | 37.101605, -84.097498 (Google Maps ↗) |
| Organizer | Redbud Ride Organizing Committee ↗ |
| Entry Fee | $0 |
| Registration | Direct Registration Link ↗ |
Robertson County Classic
📅 Nov 15, 2026Welcome to the final event of 2026! Come give it one last rip before you bury yourself in the pain cave for winter. Due to the cancellation of the Jenny Wiley event this has been created in an affordable sustainable manner so that we can move forward with the INKY Regional TT Championship and wrap up our season. This event will require no minimum number of racers and will carry on regardless of racer...
⚡ Event Details & Specifications ›
| Dataset Population | 2026 Verified Census |
| Qualified Distances | ⚡ Half Century (50 mi) |
| Event Type | Cycling Century |
| Event Status | Scheduled |
| Attendance Mode | In-Person (Offline) |
| Date | 📅 Nov 15, 2026 |
| Street Address | 207 N Main St |
| Location | Mt Olivet, KY 41064 |
| GPS Coordinates | 38.534329, -84.035228 (Google Maps ↗) |
| Organizer | Kentucky Road Racing ↗ |
| Entry Fee | $15 - $50 |
| Registration | Direct Registration Link ↗ |