Housed in a historic 19th-century building, The Jockey in Lexington, KY, unfolds over multiple spaces, each offering a unique experience: The Starting Gate, The Clubhouse, and The Paddock. Celebrated for its distinctive blend of horse racing heritage and modern bar culture, The Jockey has become a beloved destination.

In The Starting Gate, lively camaraderie sets the tone. The Clubhouse offers a refined escape for cigar enthusiasts, while The Paddock provides an open-air, street-side retreat. At The Jockey, it's not just about blending two worlds; it's about creating a one-of-a-kind experience in every space.

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The building at 131 Cheapside in Lexington, KY, constructed in 1895, stands as a significant landmark in the city's Central Business District. It was built by W. J. Loughridge, a noted hemp and tobacco broker. It was designed by Henry Hobson Richardson, a prominent architect known for his Richardsonian Romanesque style. This architectural style is known for its striking and sculptural shapes. 131 Cheapside is one of only two such buildings in downtown Lexington, the other being the Fayette County Courthouse. The property has a rich history, housing Cheapside Bar and Grill for 38 years and then The Horse and Jockey Pub and Kitchen. It became home to a bar, The Jockey, in 2024.

The Jockey evolved from the Horse and Jockey Pub and Kitchen, a beloved local Irish gastropub. In 2023, Jimmy McSweeney, one of the original founders of the gastropub, purchased the establishment and transformed it into The Jockey. This change marked a shift in focus from a traditional gastropub to a bar that celebrates Lexington's rich horse racing heritage. It also provided a place for community and hospitality at the heart of Kentucky's roots. The bar stands as a testament to this legacy. It offers an unparalleled blend of high-quality drinks, a vibrant atmosphere, and a nod to horse racing's storied past.

Today, The Jockey stands as a vibrant hub in Lexington, blending horse racing thrills with an exceptional bar experience. Patrons are welcomed into a space where the racetrack legacy is alive in every corner. From meticulously crafted cocktails inspired by legendary racehorses to a selection of local and international beers, each drink pays tribute to the sport's rich history. The bar's lively atmosphere is well-suited for both casual evenings and special events. This makes it a go-to destination for those who appreciate Kentucky's deep-rooted horse racing culture and spirited nightlife.