Come Kentucky Derby week, thoughts turn to Louisville, Kentucky, and burgoo and Mint Juleps and Derby-Pie. It’s not fair. There is a lot of very good food in Louisville. In fact, there may be more quality restaurants per capita than in any midsize American city, and that includes Portland, Seattle, and other current culinary scene-stealers.

Proof on Main

Myriad’s restaurants (Tribeca Grill, Mai House, Nobu, and San Francisco’s Rubicon among them) are very good. And it turns out that Nieporent’s Proof on Main is very good, too, though not the best food in Louisville. The fancy, arty vibe that can be a lot of fun in downtown New York can feel a little much somewhere else.

The interest right now in regional cuisine and local ingredients means smaller towns not only have a fighting chance against New York and Los Angeles, but also that they’re actually serving some of the most satisfying food in the country. In Louisville, you see this in things like a breakfast menu at North End Café with tasty but light grits, fluffy cornmeal pancakes, and Nueske’s artisanal (Kentucky) bacon; or dinner at the charming Lilly’s Bistro, with small plates including smoked trout mousse and rich rabbit croquettes with bourbon sauce.

But it’s not just regional cooking that’s good in Louisville. A popular strip mall spot, Havana Rumba, packs the crowds into two big rooms for the best Cuban food this side of Miami; Seviche is a popular not-entirely-specific Nuevo Latino restaurant; and Mayan Café is a recently relocated favorite for Yucatecan and Guatemalan food. (Everybody still calls it by its old name, Mayan Gypsy.) Try the Cochinita Pibil (pork in banana leaves) and surprisingly irresistible lima beans.

Lilly’s Bistro

No. Turns out he opened Proof on Main, a fancy place in the contemporary-art-filled 21c Museum Hotel in downtown Louisville, because the owners asked him to. “We went to the locale, and it looked just like Tribeca,” Nieporent says. “It’s in a neighborhood of cast iron buildings. Five of these small buildings were connected to house a restaurant and the hotel. We liked the people; we liked the idea that we could do something in that part of the country. The stars lined up a little bit. It’s been a healthy marriage.”

Proof is a sleek, modern restaurant, with high ceilings, white walls, lots of the hotel’s contemporary art (like a rhino head made of matchsticks), and extravagantly rich, fancily plated, high-priced Tuscan-influenced food (roasted scallops for $26, bison rib-eye for $32). Tuscany-meets-Kentucky, really: The baked octopus appetizer, a small pan of blackened octopus chunks, is outstanding, but so is the Proof Burger of Kentucky bison. There’s a good, not great, wine list, but the bar is outstanding. It makes flawless classic cocktails and some interesting signature drinks, like the Darkened Manhattan, a mix of bourbon, coffee liqueur, and sweet vermouth.

Which brings us to bourbon. It is to Louisville as Cabernet Sauvignon is to Napa. You can get all kinds here that you won’t find anywhere else. One of the best places to sample it is Bourbons Bistro, a restaurant and bar that’s got a list of around 150 bourbons, including, sometimes, the elusive Van Winkle Special Reserve 12 year and the not-too-expensive yet wonderful Four Roses Single Barrel, virtually unavailable in the United States outside Kentucky. Just let the knowledgeable bartenders guide you through.

L & N Wine Bar and Bistro

The best meal I had was a tie between Lilly’s Bistro, the restaurant owned and run by much-lauded chef Kathy Cary featuring a seasonal menu that you pretty much can’t go wrong with (for vegetarians, there’s a changing-with-the-market God Bless Our Local Farmers Plate), and L & N Wine Bar and Bistro, a newer place with a lot of wines by the glass and fairly straightforward American food (fried green tomatoes, lamb chops, and “fish & chips” made with pan-seared snapper) done very well.

But if you want Derby-Pie, try the frozen dessert case at Liquor Barn (multiple locations). And burgoo (accent on the bur), that legendary stew of road kill and okra, is, like haggis, better a memory than a meal. That said, you can try it at Bourbons Bistro or the sentimental favorite, Moonlite Bar-B-Q in Owensboro, Kentucky, which also sells canned burgoo online.

Where to Stay

There are lots of chains in Louisville, but two unique options are the Brown Hotel and the 21c Museum Hotel. The Brown is a little fusty in a not-fashionable 1940s style (like an unrenovated department store); my choice—despite expense and a few kinks in service—is the 21c, the hotel that houses Proof on Main. (Rooms start at $279 if you book through the hotel, but far better deals can be found on the travel websites.) Its lobby is a gallery of contemporary art, part of the amazing collection of the owners, with pieces by Andres Serrano, Chuck Close, Red Grooms, and others. The rooms are stylish, the touches are there—like big flat-screen TVs and art posters on the walls—but the 21c suffers from the same problem that seems to afflict a lot of superstylish hotels in medium-size cities: crazily uneven service. (Sometimes the room is cleaned, sometimes it’s not; sometimes there’s soap; sometimes there’s a fire drill.) Still, it’s comfortable and at times exciting. There’s even art in the public restrooms!

21c Museum Hotel
700 W. Main Street, Louisville, 502-217-6300 / 877-217-6400

The Brown Hotel
335 W. Broadway, Louisville, 502-583-1234

Where to Hang Out

There are a number of music venues in Louisville, but one that you might not find in the regular listings is the Pour Haus, a dive bar–cum–cool club in a sketchy part of town. Shoot some pool or check out the every-other-Wednesday spelling bees.

Pour Haus
1481 S. Shelby Street, Louisville