Bourbon, bluegrass, and betting constitute Kentucky’s own Triple Crown of activities and attractions, and there is no finer place to experience the last of these than at Churchill Downs and Keeneland in the spring. The echoes of galloping hooves ring out through these hallowed racing complexes, nearly drowning out the cheers of those wagering on ponies and sipping tall mint juleps.

The Southern–style julep features spearmint and Kentucky’s spirit of choice: bourbon. It makes sense that Kentuckians should favor this barrel-aged whiskey, as 90-percent of the nation’s supply is produced within driving distance of Lexington. The Bourbon Trail stops off at most of the distilleries in the region, including Four Roses, Woodford Reserve, and Jim Beam. It also winds along sites important to the history of bluegrass music. The unmistakable rolls of live banjos can be heard at events such as the Southland Jamboree’s Tuesday bluegrass nights and the annual Kentucky Bluegrass Music & Burgoo Festival, which pairs live music with local preparations of spicy burgoo stew.

Kentucky may seem like the ideal place to spend a rowdy weekend, but the Bluegrass State also offers attractions that cater to a slower pace of living. Bourbon Country shares territory with scenic vineyards that once produced half of the country’s wine, and historical sites such as the Revolutionary battlefield at Blue Licks State Park offer a look back at the country’s past. One of the bloodiest battles of the Civil War took place on the Perryville Battlefield, which is now the site of a museum and a reenactment every October that rates among the best of its kind.

For an even deeper look back in history, venture into Mammoth Cave National Park. The park’s more than 350 miles of caves make it the longest cave system in the world. It certainly had an effect on early guide Stephen Bishop, who described it as a "grand, gloomy and peculiar place.”