Louisville is best known as the home of the Kentucky Derby, but this eclectic city on the shores of the Ohio River deserves another accolade: top weekend trip destination for a girlfriend getaway or romantic escape. Attractions abound, from bourbon distilleries to hip shopping districts to buzzy restaurants. Even better: from most East Coast cities, it's a direct flight of just a few hours.
Take off in the afternoon to arrive in time for cocktails (preferably bourbon-based) at your downtown hotel, 21C Museum Hotel, which doubles as an actual modern art museum, and was a Fodor's 100 Hotel Award winner in 2011. The hotel's founder is a Jack Daniels heir, and her permanent collection is worth a tour whether or not you stay here. Even better: you can tour the collection with a cocktail in hand.
Keep it local with dinner at the hotel's award-winning American restaurant Proof on Main for creative American standouts like an addictive bison burger, and the locally raised bone-in pork chop with seasonal sides. Don't miss the truffle fries. After dinner, saunter across the street to the popular St. Charles Exchange, a bar known for cocktails like gingery Bourbon Buck and Admiral Dawson's 1772 Punch.
Arrange for a car service like Mint Julep Tours to do the driving today. First stop: the newly opened Please and Thank You, which opens at 9 am. This cafe-cum-record store is the spot for stellar coffee and habanero egg-cheese rolls, or just-made muffins. That's the fuel you'll need for the drive out to Makers Mark on the Bourbon Trail. Makers Mark is one of the closest distilleries to Louisville (the drive is just over an hour), and offers the most memorable tour-and-tasting experience.
At Makers Mark, you'll explore every step of the production process, from grain blending and fermentation to distillation and bottling. Then you'll do a tasting of their signature bourbon and second-expression, the rich, spicy Makers 46. Visitors can even sign and hand-dip their own bottle of bourbon in the brand's signature red wax seal. The pastoral grounds of Makers Mark are stunning—the perfect place for a picnic. Fortunately, you can pick up those supplies right on the campus, at the Toll Gate Cafe (get the pulled pork sandwich).
After lunch, feel free to sip bourbon on the way back to the city (Mint Julep Tours makes it easy with ice and water stocked in the car). Freshen up at 21C then head out to the stylish NuLu neighborhood, chockablock with hip restaurants and stylish boutique shops. Browse the neighborhood, before stopping into Garage Bar for drinks and snacks. The best way to start is with thin-cut country ham served with crusty bread, red-eye gravy mayo, and carrot marmalade (unexpected and totally delicious). If the weather is favorable, you'll be sitting outside in an astro-turfed yard with Louisville's hip crowd.
For dinner, head a block in any direction and you'll land in the farmer-owned and sourced Harvest, the Yucatan-inspired Mayan Cafe, or the inspired American Decca, with its expansive outdoor garden. Regardless of where you dine, after dinner you'll go subterranean at Decca's Lounge for live music and serious cocktails.
Downtown is quiet on Sunday mornings, so you need to head to where the locals go. For brunch, cab it up to the Highland neighborhood to Highland Morning for their locally renowned Baja Benedict—corn cakes topped with eggs, chorizo, and salsa. Their fresh berry-studded pancakes are also worth the trip.
Walk off the gargantuan portions by browsing shops up and down the retail strip on Bardstown Road. You'll find locally-made gifts at Consider, vintage clothing deals at Urban Attic, and souvenirs at WHY Louisville. To ease into your trip home, end on a mellow note with a local microbrew on the patio of O'Shea's Irish Pub.
21C Museum Hotel courtesy of Kenneth-Hayden/21C Museum Hotel; Proof on Main courtesy of Magnus Lindqvist; Makers Mark Distillery courtesy of Erica Duecy; Garage Bar courtesy of Magnus Lindqvist/Garage Bar; Highland Mornings courtesy of Erica Duecy
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