The 10 Best Road Races in Kentucky!

Kentucky is a great place to run a marathon if you like running on flat ground and paved surfaces, but it’s an even better place if you want to challenge yourself by running up and down hills, along unpaved trails, and even over mountains. From major marathons that qualify runners for big races like the Boston Marathon to smaller gatherings designed for people looking for more challenge and less glory, the 10 best road races in Kentucky offer something for all types of running personalities.

1. The Kentucky Derby Festival Marathon, Louisville, KY

Every year as part of the festivities leading up to the annual running of the Kentucky Derby, the Kentucky Derby Festival hosts the Kentucky Derby Festival Marathon and Minimarathon races. The Marathon is a 26.2-mile race, and the Minimarathon is a 13.1-mile race. Both take participants through the streets and parks of Louisville, Kentucky, and spots sell out every year.

2. Ironman Louisville, Louisville, KY

Ironman hosts a triathlon every year in Louisville, Kentucky, bringing some of the top triathletes in the region to downtown Louisville to compete. The triathlon begins with a 2.4-mile swim in the Ohio River. After that, competitors take to their bikes for a 112-mile cycling course through the rolling hills of the Louisville Metro and Oldham County. The final leg of the race is a 26.2-mile marathon.

3. Hatfield McCoy Marathon

The Hatfield McCoy Marathon is an intense race that takes runners through the mountains of western Kentucky and eastern West Virginia. Hosted annually, the race offers three different lengths to cater to runners of every level: a full 26.2-mile marathon, a 13.1-mile half marathon, and a 5K race. Elevation changes are significant in this marathon—at one point runners run up and back down a mountain.

4. Land Between the Lakes Trail Run, Grand Rivers, KY

Each year, runners converge in Grand Rivers, Kentucky, for the annual Land Between the Lakes Trail Run. This event features both a 26.2-mile marathon and a 50-mile ultra-marathon for serious runners. These marathons have some elevation changes, but for the most part they’re relatively flat. Runners enjoy scenic views of the lakes, sailboats, and the Land Between the Lakes National Recreation Area.

5. Iron Horse Half Marathon, Midway, KY

The Iron Horse Half Marathon is a 13.1-mile race run every year in Midway, Kentucky. The race takes participants through rolling fields and past horse farms that are unique to Kentucky’s horse country. The race has been the recipients of many honors: it was named as one of the top half marathons in the U.S. by Runner’s World and one of the top races worth traveling for by TripAdvisor’s FlipKey.

6. Run the Bluegrass, Lexington, KY

The annual Run the Bluegrass half marathon race in Lexington, Kentucky, bills itself as “America’s prettiest half marathon.” Runners follows a 13.1-mile trail through Keeneland Race Track and past some of the most idyllic horse farms in Kentucky. Rolling hills, flat lands covered in Kentucky bluegrass, and romping horses are some of the sites you can expect to take in while participating in this annual race.

7. Big Turtle 50 Miler, Morehead, KY

Visitors to Morehead, Kentucky, can participate in the annual Big Turtle 50 Miler races. Two race lengths are offered for participants: a traditional 26.2-mile marathon and a 50-mile double marathon. Runners traverse the northern section of the Sheltowee Trace National Recreation Trail. Runners of the 26-mile marathon double back halfway through the course while 50-milers run up and back the 25-mile trail.

8. The Backside Trail Marathon, Louisville, KY

The Backside Trail Marathon and Half Marathon races are run annually through Cherokee and Seneca parks in Louisville, Kentucky. Both a full 26.2-mile and a half 13.1-mile course are available to participants. Because these races are run on trails that traverse several hills, they are more difficult than typical flat-ground or pavement races. Marathon runners run the 13.1-mile trail twice for completion.

9. Horse Capital Marathon, Lexington, KY

Runners interested in qualifying for the Boston Marathon can do so by running in the Horse Capital Marathon in Lexington, Kentucky. Two races are offered as part of event: a 26.2-mile full marathon and a 13.1-mile half marathon. Both the full and half marathons takes runners through scenic bluegrass country and past dozens of horse farms, and the entre course is on paved surfaces.

10. BG26.2, Bowling Green, KY

The BG26.2 is an annual road race in Bowling Green, Kentucky, that allows participants to run either a full 26.2-mile marathon or a half 13.1-mile marathon. This race is popular for individuals aspiring to compete in the Boston Marathon because its recognized as a qualifying race. Runners follow a paved path through downtown Bowling Green and the Western Kentucky University campus.

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