For guests arriving early, staying through Sunday, or looking for something to enjoy beyond Keeneland, Castle & Key is one of the most beautiful distilleries in Kentucky. The historic grounds are stunning, and it’s located near other favorites like Woodford Reserve, making it a great addition to a day of exploring the Bourbon Trail. Tour tickets often book well in advance, especially over holiday weekends, but you can still enjoy the property without a reservation. Visitors are welcome to explore the grounds, browse the gift shop, and relax with a cocktail at the onsite bar.
Keeneland is one of Kentucky’s most beloved traditions and a must-see for first-time visitors. Known for its historic charm and beautiful grounds, this iconic race track hosts live thoroughbred racing every April and October. It’s a classic Kentucky experience, whether you’re stopping by on Friday before the wedding, joining the bride and groom at the races on Saturday, or exploring on Sunday. Guests can watch the races, stroll the paddock, place bets, enjoy food and drinks, and take in the atmosphere that makes Keeneland so special. Even those who aren’t deeply into horse racing will love the scenery, excitement, and sense of tradition. Tickets are sold in advance through the Keeneland website, and popular days often sell out quickly during the fall meet. We recommend purchasing early if you plan to go.
It wouldn’t be fall in Kentucky without cheering on the Cats. We don’t yet know if it will be a home or away game that weekend, but we’ll be rooting for Kentucky either way. If it’s a home game, the action is at Kroger Field, and tickets are sold online. There’s nothing quite like an SEC tailgate, and if you wear blue, you’ll fit right in. If it’s an away game, we recommend watching with the locals at Tin Roof, where Dylan bartended his first year in Lexington. Stapleton’s go-to order there is the loaded tater tots and a John Wall shot.