Sign up for fun cycling rides, tours and races in the Southern Indiana and Greater Louisville area.
Southern Indiana is the center of the region’s best cycling. This year is packed with must-go cycling events, from road to mountain bike and cyclocross. Let’s highlight a few of the big cycling rides, tours and races held in the Southern Indiana and greater Louisville area that you’ll want to register for and plan a trip to participate in. These rides vary from urban road cycling to riding through the Indiana countryside and into the Indiana Knobs, plus single track racing in the Kentucky hills.
This is by no means a definitive list. There are numerous local rides and races taking place in the area throughout the year. I’ve compiled a list of highlighted area cycling events perfect for a trip to SoIN. Plan your next getaway to Clark and Floyd counties to attend one, or many, of these great cycling events:
Tour de Lou
April 12, 2026
This Louisville bicycle tour is part of the Kentucky Derby Festival. The open course (meaning streets are not closed for the event) offers 25-miles, 35-miles and 62.1-miles (Metric Century) distances. New in 2026, the tour will offer a 12-mile ride, perfect for those new to cycling. All routes for 2026 begin and end at Big Four Bridge. This is the perfect way to experience Louisville, Kentucky by bicycle. You’ll ride through Downtown Louisville, historic Old Louisville, through multiple scenic Olmsted Parks, and get an exclusive opportunity to cycle through Churchill Downs, home of the Kentucky Derby. Check out more about Tour de Lou and how to register for the event.
3 Steeples Bike Ride
May 16, 2026
This ride based in Floyds Knobs, Indiana, has been going strong for 12 years. Cyclists can expect a scenic ride through the rolling hills of the Indiana Knobs. You can choose from a family-5.5 miles, 26 miles, 40 miles or 50 miles. The 5.5-mile family ride features a SAG stop with activities for kids. The tour is also known for homemade treats and local strawberries at its SAG stop. Learn more about the 3 Steeples Bike Ride and registration information.
Mayor’s Hike, Bike & Paddle
May 25, 2026
This annual event takes place Memorial Day Weekend. Participants can choose from a hiking course at the waterfront (Hike #2 crosses into Indiana!), a closed-course cycling ride throughout Louisville that includes Frederick Law Olmsted-designed Shawnee Park or a kayaking route that takes paddlers through the McAlpine Locks. The ride starts and finishes at the Great Lawn in Louisville’s Waterfront Park. The event kicks off with fun, music and free fitness activities, like Yoga, Tai Chi, Zumba, Fitness classes, and workout circuits. Learn more about the Mayor’s Hike, Bike & Paddle.
Juneteenth Solidarity Ride
June 13, 2026
The 6th annual Juneteenth Solidarity Ride marks the Juneteenth holiday that commemorates the emancipation of enslaved people in the U.S. It starts and stops at Shawnee Park, a cornerstone of the Frederick Law Olmsted park system located in West Louisville. There are 3 route options: 13, 24, and 50 miles. The open course ride takes cyclists along the Southwestern Parkway and Ohio Levee Trail and into the Highlands to either Willow Park, Cherokee Park or Seneca Park, depending on your ride option. Explore more about the Juneteenth Solidarity Ride and how to register.
My Old Kentucky Home Bicycle Tour
August 8, 2026
The 46th My Old Kentucky Home Bicycle Tour begins and ends at 3rd Turn Oldham Gardens in Crestwood, Ky., east of Louisville. OKHT offers three routes: 20, 40 or 62.1 miles and takes cyclists through the rolling hills and farmland in Kentucky’s Oldham County. Explore more about My Old Kentucky Home Tour.
IRONMAN 70.3
Paused in 2026
The IRONMAN 70.3 is Louisville's premier triathlon event. The event is on pause in 2026 as the city undergoes major infrastructure improvements. IRONMAN is also a great spectator sport. Even if you're not a participant, you can find a spot along the cycling, running or swimming course to cheer on the endurance athletes.
Bike to Beat Cancer
September 12, 2026
This fundraising ride supports Norton Cancer Institute’s and Norton Children's Cancer Institute’s mission to cure cancer and eliminate suffering. The ride starts and ends at Norton Cancer Institute (Brownsboro) in Louisville’s East End. Participants can choose from a 5-, 15-, 35- or 65-mile supported ride, or a virtual ride. The event includes a 1-mile Fun Walk and a Celebration of Courage, featuring food, live music, bounce houses and fun activities for all ages. Find out more about Bike to Beat Cancer.
Harvest Homecoming Bicycle Tour
September 26, 2026
A part of the Harvest Homecoming Festival in New Albany, Ind., the bicycle tour offers cyclists scenic fall views of the Indiana countryside and Ohio River Valley. The ride starts and ends at the Lanesville Heritage Site. There are 5-, 28-, 40- and 69-mile routes. Learn more about the Harvest Homecoming Bicycle Tour
Don’t wait for a bicycle event to visit Southern Indiana for a cycling getaway. Check out Cycling in Southern Indiana — A Bike Ride for Every Cyclist for ideas of where to ride.
