21c Museum Hotel Louisville
Begin your journey here, with this unique hotel stay. Set in five restored 19th-century warehouses, it offers stylish rooms, immersive art installations that are open 24/7, and a stone's throw from Proof on Main restaurant - a great local spot.
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BookWhiskey Thief Distilling Co. Louisville
Whiskey Thief Distilling Company sits on a 127-acre farm in Franklin County, KY, where they grow their own grains to make single-barrel bourbon. They serve their bourbon uncut and unfiltered, letting the full flavor shine through. Visitors can try the unique “thieving” experience—sampling and filling bottles straight from the barrel using a traditional whiskey thief. It’s a hands-on way to connect with the craft and taste bourbon at its purest.
See MoreRabbit Hole Distillery
The Overlook Bar sits atop Rabbit Hole Distillery in Louisville, offering sweeping views of the skyline and the Ohio River. Designed with mid-century flair and original artwork, the space pairs sleek style with a standout cocktail menu created in collaboration with the team behind NYC’s Death & Co. Drinks spotlight Rabbit Hole’s bourbon, rye, and gin, and the small food menu includes thoughtful pairings like charcuterie, snacks, and seasonal bites served with a view.
See MoreEvan Williams Bourbon Experience
ON3 Bar, perched on the third floor of the Evan Williams Bourbon Experience in Louisville, is a bright, loft-style space with exposed brick, big windows, and a city feel. It’s known for creative cocktails, bourbon flights, and the occasional rare pour from the Heaven Hill lineup. Mixologist Karla Plott runs the bar, adding her own spin to the classics. Depending on the day, you might even catch a Kentucky-only bottle behind the bar.
See MoreMichter's Fort Nelson Distillery
Housed in a restored 1800s building, Michter's is a working micro-distillery for small-batch experiments, plus guided tours and tastings. The real highlight? The Bar at Fort Nelson—a spot for seriously good cocktails made with renowned attention to detail.
See MoreThe Café
Grab a hearty lunch here on your way out of town. The shrimp and grits and their fried chicken come highly recommended.
See MoreBulleit Distilling Co.
Bulleit Distilling Co. in Shelbyville, KY, is known for its bold, high-rye bourbon and rye whiskeys that lean spicy and smooth. The distillery, opened in 2017, blends cutting-edge distillation with a strong focus on sustainability. Visitors can take tours, explore sensory tastings, and enjoy cocktails at the bar. Though the brand launched in 1987, its roots trace back to the 1830s with original distiller Augustus Bulleit.
See MoreHeaven's Door Distillery
Heaven’s Door Distillery, founded by Bob Dylan and located in Pleasureville, KY, blends history, art, and sustainability across its 160-acre site. The distillery features two stillhouses in old horse barns, an 18th-century grist mill, and cabins, all powered by underground aquifers and geothermal systems. Visitors can taste small-batch whiskeys in the Visitor Center overlooking Six Mile Creek, while Dylan’s artwork appears on select bottles. They also run The Last Refuge, a historic Louisville church turned whiskey gallery.
See MoreCastle & Key Distillery
Castle & Key Distillery sits on the restored grounds of the Old Taylor Distillery, built in 1887 by bourbon pioneer Col. E.H. Taylor Jr. The site blends European-style architecture—a castle, sunken garden, and springhouse—with modern distilling. Using Vendome stills and locally sourced grains, Castle & Key produces bourbon, gin, and vodka. Tours and tastings walk guests through the striking setting and layered history, offering a look at how the past shapes their present-day approach to spirits.
See MoreWoodford Reserve Distillery
Woodford Reserve Distillery in Versailles, KY, has been making bourbon since 1812 in a historic, National Landmark building dating back to 1838. Known for its triple-pot distillation and careful attention to flavor, it uses a balanced grain recipe, limestone-filtered water, and a unique fermentation process. The distillery blends history and craft, preserving its classic architecture while producing distinctive Kentucky bourbon that honors its roots.
See MoreThe Stave
A great stop for a bite along Glenn’s Creek that draws a mix of locals and Bourbon Trail travelers. It’s known for hot browns, bourbon bread pudding, a solid bourbon list with tasting flights, and a covered patio that looks out over the water. Perfectly located during your stops at Woodford Reserve and Castle & Key. Locking in a reservation is a good idea for this spot.
See MoreThe Delegate Hotel, Common Bond Hotel Collection
Based in downtown Frankfort, The Delegate Hotel is a converted warehouse with great character, including original, brick-walled rooms and a clean, modern look. Just enough character here without trying too hard. There’s an on-site restaurant, Cypress & Oak, and you’re a short drive from several Bourbon Trail distilleries.
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