As a visual artist, I’m drawn to the fringes in a lot of ways— constantly aware of the weird, intriguing, and special things that lie below the surface or beyond the bulk of the crowd. What follows is a guide to some of my favorite creative experiences in Lexington. If you are an artist, creative-type, or just looking to have your curiosity piqued while you’re in town, I think you’ll find this list mighty helpful.


  • 21c Museum Hotel: If you love art, you can’t not stay at 21c. The hotel doubles as a contemporary art museum, with world-class art bathing the spaces throughout, from the lobby, to the hallways, hotel rooms, and more.

Lexington influencer, Ciara LeRoy in 21c Hotel room.

21c Museum Hotel 


  • The Parachute Factory: The Parachute Factory is a non-profit art gallery located on the Northside of downtown Lexington. The space houses rotating exhibitions by regional artists and also serves as a multi-use space for community events and other artistic endeavors.
  • Lexington Art League: The Lexington Art League, located inside of the historic Loudoun House, is stunning and inspiring from the inside out. LAL is home to an engaging and diverse series of rotating exhibitions, artist’s studios, and frequent public events.
  • Josephine Sculpture Park: The 30 acre sculpture park is home to nearly 70 works of art. Sure to level up your typical walk in the park.
  • Henry Clay Estate: This historical home sits on beautiful, sprawling grounds that are perfect for picnics, jogs, and creative photo shoots.

Exterior of Parachute Factory with Ciara LeRoy sitting on steps.

The Parachute Factory


  • Lockbox at 21c: Lockbox is the house restaurant for the 21c Lexington hotel. This is one of my favorite spots to eat because of all of the art eye candy and the artful plating of every dish.
  • Middle Fork: Whenever I’m at Middle Fork, I feel like I’m dining in NYC. Some of the most unique and thoughtful dishes I’ve ever had, have come out of the Middle Fork kitchen.
  • Favor: Favor is tucked behind Arcadium Bar, slinging a combination of comfort and higher concept dishes.
  • Arirang Garden Korean BBQ: The thing I love about Korean BBQ is that it feels like a collaboration— the restaurant provides raw meats and a variety of yummy sides and condiments, and you get to cook tabletop and dress your meal however you’d like. Arirang elevates dinner to a cultural and creative experience.


Ciara LeRoy enjoying a drink at Lockbox.



  • Bar Ona: Walk too fast, and you’ll miss this gem. Ona is my forever favorite spot to get an expertly crafted cocktail and a dimly lit corner to enjoy it in.
  • Lussi Brown: Located right next to Bar Ona, Lussi Brown slings amazing hand-crafted espresso beverages, teas, and boozy drinks (after 4pm).



  • Sqecial Media: Located near the University of Kentucky, Sqecial Media is my place to find interesting new & used art books, and a ton of other unique gifts to treat yourself and others, like candles, an impressive incense selection, journals, accessories, decor, and more.
  • Street Scene Vintage: Street Scene has an expertly curated selection of fine vintage clothing and homeware, along with new items sourced from independent artisans and other small businesses.
  • The Domestic: The Domestic is another one of my favorite places to shop vintage in Lexington. This huge, warehouse style spot is primarily focused on vintage home decor, but they also have an impressive room filled with rad vintage clothing.