Louisville, KY

Classic Americana – A Weekend In Louisville

Amber Gibson

There’s more than bourbon and horses in Derby City

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Kentucky’s largest city is where the bourbon trail begins and Main Street is like a walkable Napa Valley of urban distilleries, but there’s much more to do in Louisville than distillery tours. The 19th century cast iron facades along Main Street are beautifully preserved while the restaurants and boutiques in the NuLu neighborhood are your best bet for local shopping and independent restaurants. Butchertown is another hip destination just east of downtown Louisville, a former meatpacking district that’s now home to Butchertown Market, Play Dance Bar for drag shows and dance parties and a 24-hour skate park. Here’s your guide to a perfect weekend getaway.

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Bet on horse racing at Churchill Downs

There’s horse racing at Churchill Downs every week during the spring and fall meets, typically April through May and October through November. Outside of the Kentucky Derby, it’s pretty easy to get tickets the day of at the box office. Entry is just $5, and you can ask for the seats closest to the finish line. During summer, there’s Downs After Dark night racing too. Even if there isn’t a race on during your visit, you can learn about the history and heritage of Churchill Downs at the Derby Museum, before sitting down for dinner at the stadium’s first year-round restaurant, Matt Winn’s Steakhouse, overlooking the track. The modern steakhouse has an extensive bourbon selection and equally impressive wine list. American wagyu beef comes from nearby Blackhawk Farms and is cooked to perfection but even vegetarians will be satisfied with hearty sides like wild mushroom gratin, crème fraîche whipped potatoes and haricot verts with garlic chips and caramelized shallots. Plus, three roving carts tempt diners with elaborate cheese and charcuterie platters, seafood towers and desserts. Pro Tip: Bourbon pairs especially well with country ham.

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Enjoy horses, bourbon and farm-to-table fare at Hermitage Farm

A working thoroughbred farm since 1936, Hermitage Farm recently opened to the public as an agritourism destination combining Louisvile’s star attractions – horses and bourbon. Begin with a tour to see the inner workings of a horse farm before visiting Barn8 for a tasting of some of Kentucky’s best bourbons including vintage options and single barrel selects from small craft distilleries. You can even meet the famous racing studs once they’re back from their winter vacation in Florida. Enjoy brunch or dinner at Barn8, where you can dine in an original horse stall and most of the produce comes from the greenhouse next door.

Walk off a decadent meal while enjoying public art installations along the art walk and if you’ve had too much bourbon to drive back to Louisville, you can even spend the night in the five-bedroom guest house on property.

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Visit Muhammad Ali's grave and museum

Muhammad Ali is Louisville’s most famous son, and the Muhammad Ali Center in downtown Louisville is an invitation to explore the world champion boxer, artist and activist’s inspiring life story and core values. You can even visit Muhammad Ali’s grave at historic Cave Hill Cemetery and sit on the granite benches while paying respects for a moment of reflection. The Victorian era cemetery also doubles as an arboretum and features impressively ornate burial sites for some of Louisville’s most prominent historic figures. Entry is complimentary and visitors can drive through or take a walk along the meandering paths.

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Take a walk across the Big Four Bridge

Another great place for a stroll is across the Big Four Bridge, a former railroad bridge that crosses the Ohio River. You can walk from Kentucky to Indiana across the half mile bridge and access is limited to pedestrians and cyclists, so it’s a great way to squeeze in exercise and iconic views of the city. At night, the bridge is lit up in seasonal colors and during summer there are often free concerts and other outdoor events in the adjacent waterfront park.

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Have a nightcap at a speakeasy

There are several speakeasy-themed bars in Louisville, but Hell or High Water is the most upscale and a personal favorite. Tucked behind Whiskey Row right next to the convention center, the unmarked storefront has vintage sheet music ephemera on the walls, an innocent and nondescript facade for the sexy cocktail lounge below. You’ll need a reservation to get in, and the speakeasy is full of private rooms and alcoves for absolute discretion. Pin + Proof at a Omni Louisville is another fun opttion, a bowling and speakeasy hybrid hidden in a swanky hotel.

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Where to Stay

21c Museum Hotel is the city’s most prominent boutique property, the original hotel in an irreverent brand that now has nine hotels throughout the South and Midwest. Founded by contemporary art collectors Laura Lee Brown and Steve Wilson, each 21c property combines a contemporary art museum with a hotel and chef-driven restaurant for a new approach to hospitality. The museum is free to the public and worth visiting even if you aren’t a hotel guest, with regularly rotating exhibits that are always provocative and beautifully curated.

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Hotel Distil, part of Marriott’s Autograph Collection, is Louisville’s newest luxury property, located on historic Whiskey Row. They embrace the whiskey theme wholeheartedly – Repeal Day, when Prohibition was repealed, is celebrated nightly with free drinks for hotel guests and Bitters End is the only rooftop bar in the neighborhood, specializing in craft cocktails with house-made bitters.

The Omni Louisville is another comfortable choice, a larger LEED Silver certified hotel with a full-service spa, fitness center and pool. The lobby is elegantly designed to look like a deconstructed bourbon barrel in a cheeky nod to Louisville’s past.

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Amber Gibson specializes in luxury travel, food, wine and wellness. Her work has appeared in Travel + Leisure, Conde Nast Traveler, National Geographic Traveler, Robb Report, Departures, Hemispheres, Saveur, Bon Appétit, Fodor's, NPR, NBC and more. Champagne, dark chocolate and gelato are her biggest weaknesses.

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