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 19, 2025
This Louisville bicycle tour is part of the Kentucky Derby Festival. The open course (meaning streets are not closed for the event) offers 20-miles, 35-miles and 62.1-miles (Metric Century) distances. The tour begins and ends at NuLu Marketplace on Main Street in Louisville’s NuLu neighborhood. 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. The Metric Century route even takes you into Indiana. Check out more about Tour de Lou and how to register for the event.
Bluegrass Mountain Cup Duffield XC & Enduro
April 25-27, 2025
Set in a favorite local mountain biking destination south of Louisville in West Point, Ky. the Bluegrass Mountain Cup includes a cross-country mountain bike loop and Enduro stage races. Find out more on registration and details about the Bluegrass Mountain Cup.
3 Steeples Bike Ride
May 17, 2025
This ride based in Floyds Knobs, Indiana, has been going strong for 11 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 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 26, 2025
This annual event takes place Memorial Day Weekend. Participants can choose from a hiking course at the waterfront, a closed-course cycling ride throughout Louisville that includes multiple Frederick Law Olmsted Parks 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 14, 2025
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.
Le Tour de Pork
August 2, 2025
Le Tour de Pork is a fundraising ride supporting the efforts of the Ohio River Greenway. The 26-mile and 50-mile routes take cyclists through the rolling countryside of neighboring Harrison County, Indiana. It starts and ends at Turtle Run Winery, in Corydon, Ind. The event becomes a festival of sorts with food trucks, live music, and wine available for tastings and purchase. Get all the details on Le Tour de Pork.
My Old Kentucky Home Bicycle Tour
August 9, 2025
The 45th My Old Kentucky Home Bicycle Tour begins and ends at 3rd Turn Oldham Gardens in Crestwood, Ky., east of Louisville. OKHT offers four routes: 20, 40, 50 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
August 17, 2025
The IRONMAN returns to Louisville in August! It is the premier triathlon event. IRONMAN is also a great spectator sport. Find a spot along the cycling, running or swimming course to cheer on the endurance athletes. Take a look at the IRONMAN schedule.
Bike to Beat Cancer
September 13, 2025
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-, 65-, or 100-mile supported ride, or a virtual ride. Find out more about Bike to Beat Cancer.
Harvest Homecoming Bicycle Tour
September 27, 2025
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 66-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.
