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Click on the event title for more information on the events listed below:


PNC Tour de Lou
April 16th, 2023
Louisville, KY

Tour de Lou logo

The Derby Festival's annual cycling experience, the PNC Tour de Lou, is a unique way to tour Louisville on two wheels and celebrates its 10th year in 2023. The event has moved to a Sunday and cyclists will once again have the opportunity to ride through the home of the Kentucky Derby. In addition, the Metric Century course encompasses two states, Kentucky and Indiana. A virtual alternative is also available for those who prefer to log their miles on their own. Riders who participate in the virtual option can still choose to complete the 20, 35 or 62.1 mile distance. Participants can ride at their own pace, and even their own route, over multiple days.

Redbud Ride
April 22nd, 2023
London, KY

Redbud Ride logo

Register Today! Join us for one of the most beautiful rides in Kentucky. Experience the beauty of Spring in bloom with hundreds of other riders of all ages! This ride is a rite of spring.

Limestone Cycling Tour
April 29th, 2023
Maysville, KY

Limestone Bicycle Tour logo

The Limestone Bicycle Tour is back in 2023 after a year's hiatus. The Tour offers routes of 26, 44, 67 (3400 feet climbing) and 100 miles (5400 feet climbing). Mason County, KY has rolling hills, and the longer routes include some 9-10% (or more) climbs. The ride benefits the 2022 Eastern Kentucky flood relief fund.

Pedal Putnam
May 6th, 2023
Greencastle, IN

Pedal Putnam logo

Pedal Putnam is a chip-timed cycling event that offers three routes of different lengths (62, 40 & 12 miles), designed for families and cyclists of all abilities to enjoy Putnam County's covered bridges, waterfalls, public art, and stunning countryside. Roads will be marked noting every turn, fully stocked SAG stops await riders on each route, and all participants will receive a custom soft-style event t-shirt. Stick around after the ride for music, food and drink, vendors, local shopping, and an awards presentation to the top three finishers in each age group.

Horsey Hundred
May 26-28, 2023
Georgetown, KY

Horsey 100 logo

The Horsey Hundred is the premier cycling event in Kentucky and the signature event of the Bluegrass Cycling Club. We've come a long way since the inaugural Horsey Hundred was held at the Kentucky Horse Park (Lexington, KY) in 1978. The first event featured 50-mile routes on Saturday and Sunday with an optional Century ride on Saturday. No records exist of how many participated the first year, but the next year (1979) had 65 participants. The event now hosts some 3,000 riders.

Old Kentucky Home Tour
June 17th, 2023
Yew Botanical Gardens
Crestwood, KY

Old Kentucky Home Tour logo

The OKHT will again explore scenic Oldham County in 2023 with ride lengths of 62, 40 and 20 miles. The "World Famous Cookie Stop" returns again. The 62-mile route includes parts of Louisville, and all 3 routes traverse the rolling hills of Oldham County. Routes also visit historic LaGrange.

July 22-29, 2023


RAGBRAI--The Register's Annual Great Bicycle Ride Across Iowa--celebrates its 50th anniversary in 2023. Event organizers are offering a Golden Jersey giveaway to celebrate. The route is still pending, but is usually about 500 miles with around 10,000 to 15,000 feet of climbing. RAGBRAI has a 10,000-rider limit, and that number usually includes a sizeable contingent from SIW. For more information, contact Joe Gutmann.

Bluegrass Century
August 26th, 2023
Owensboro, KY

Bluegrass Century logo

The Bluegrass Century offers routes of 100, 62 and 30 miles. Earliest registration ends January 31st, with several other discount periods available. Online registration deadline is August 23rd. If you register before July 16th, you are guaranteed a t-shirt and swag bag. The Bluegrass Century benefits Young Life.