Gray-washed tobacco barns commingle with pristine thoroughbred stables. Paddock fences frame rolling pastures along rural lanes. Ghostly white rick houses stand sentinel-like around distinctive bourbon distilleries, each telling a unique story through land, architecture, and tradition.

With every mile clocked on these winding country roads, we’re more enamored with Kentucky. Two words: It’s authentic.

From rubbing elbows over a biscuits-and-gravy breakfast with a who’s who of the horse world at Keeneland’s scruffy Track Kitchen to grabbing a tumbler of whiskey at Bourbon on Rye in downtown Lexington, Kentucky lives what it is—fun and full of wonder—and we love it. Two more words: Immerse yourself.

Lexington

Keeneland

There’s nothing like a perfect spring or fall day spent at this internationally renowned race track and National Historic Landmark in Lexington, Horse Capital of the World: live edge-of-the-seat horseracing, gorgeous grounds, food truck tailgating on “The Hill,” Bluegrass music, perhaps a backstretch tour to watch a racehorse get new shoes. For us, Keeneland connects the two things Kentucky is most famous for–horses and bourbon–in a very personal way, one reflected on our Pinhook labels.

View

Tolly-Ho

Bite into a perfectly greasy Ho-Burger, served with a pile of fried mushrooms and fried egg topper. Wash it down with an Ale-8-One, the citrusy-gingery soft drink invented in Kentucky. This 24-hour old-school spot is Lexington’s favorite last stop of the night. Ours, too.

View

Bluegrass Tavern

Yeah, it’s a dive, but Lexington’s Bluegrass Tavern didn’t become home to Kentucky’s largest bourbon selection by trying to be another pretty face. Instead, it sticks to its roots: cheap drinks, live music, dark corners, and an obsession with pickled eggs. What’s your mood? The bartenders will match a whiskey or wine to it. Lots of bars have crazy-huge whiskey selections; this place remains a step ahead of them all.

View

Columbia Steak House

The house special at this downtown steakhouse was named for Lexington rock ‘n roll DJ Tom Kindall, better known as the Nighthawk. It’s an impeccably plated beef tenderloin, broiled in garlic butter and served with a massive baked potato and signature Diego salad, and clocks in rather amazingly at under $20. The dining room here has been graced over time by a who’s who of Kentucky luminaries, from senators and sports figures to writers and artists. Also, regulars like us.

View

Old Frankfort Pike

These 15.5 miles of National Scenic Byway unspool through the heart of Kentucky Horse Country between Lexington and Woodford County. Take in the historic farms, dry-laid stone walls, and rolling hills, the vista around each bend more scenic than the last. Keep an eye out for the beautiful new statue of Triple Crown legend Secretariat, standing in the traffic circle at Alexandria Drive and perfect for snapping selfies. 

View

Lexington and Louisville

Justins' House of Bourbon

Everybody needs friends like the Justins – as in bourbon collectors Justin Sloan and Justin Thompson, the owners behind Justins’ House of Bourbon, with locations in both Louisville and Lexington. They've curated a collection of special and rare bourbons and are perpetually seeking out vintage bottlings from beloved distilleries. (They also offer a unique bourbon concierge service.) There’s something here for everyone: You can spend $30,000 on a rare, historic bottle, but you can also find a good bourbon for $20. We recommend sampling a tipple or two at the tasting bar.

View

Louisville

The Pine Room

Southern-inflected cuisine, cocktail artistry, live piano music lilting across an airy dining room. Find these delights at the Pine Room, off the beaten path in Louisville’s Harrods Creek neighborhood. The restaurant's friendly, welcoming vibe, unbelievably tasty food, and exquisite cocktails combine accessibility and quality in a way that reminds us of what we do at Pinhook.

View

Bardstown 

Willett Distillery

In Bardstown, known as the Bourbon Capital of the World, the family-owned and operated Willett Distillery produces a boutique, small-batch collection of whiskeys with cheeky tasting notes such as “vanilla lemon cake,” “Fun Dip candy,” and “Christmas.” Mmm. A visit to the distillery will not be complete until you've settled into a table at the on-site Bar at Willett.

View

Frankfort

Castle & Key Distillery

We love a fairy tale come to life, especially one with a whiskey pedigree that reaches back to 1887 and one of the fathers of the modern bourbon industry. The castle-inspired architecture of the formerly abandoned Old Taylor Distillery was brought back to life in 2014, when the owners of the future Castle & Key Distillery set about restoring the property. The first whiskey distilled and aged here in nearly 50 years? Pinhook’s own Flagship Rye, released in 2020.

View