Things to do in Kentucky

About 150,000 racegoers will flock to the Churchill Downs track in Louisville, Kentucky, to watch the 136th running of the world's most famous horse race. But more than that, the crowds will enjoy the week-long party that surrounds the two-minute spectacle. Partying spills over into the pageantry of the genteel south in the form of preposterous hats, marching bands and industrial quantities of mint julep.

Beyond the pro forma hangover that overindulgence brings, though, Kentucky does offer some surprises. While everyone knows it for the Derby, in the past few years, the Bluegrass State — and Louisville, in particular — has been positioning itself as the US's latest cultural centre, with art galleries, a state-of-the-art museum dedicated to the greatest boxer of all time and America's "best" hotel.

Here's our pick of the best of old and new Kentucky:

1. Diners and drive-ins

By Churchill Downs sits Wagner's, a family-run diner and pharmacy since 1922, with banquettes and stools — and refreshingly brassy staff in the land of southern hospitality. It's where the jockeys dine and the history of the race is written all over the walls, with pictures of past winners and famous figures who have graced the pharmacy's fountain over the years. Breakfasts are waffles and pancakes, eggs over-easy and crispy meat. For lunch, there's the Derby sandwich: honey-glazed meat, melted Swiss cheese and mayo. For the 1950s drive-in experience, there's the Parkette Drive-In in Lexington, an hour to the east, which still has tailgate parties and car-hops. Park the right side of the intercom! Inside this all-American diner, which was opened in 1951, there's a jukebox and chessboard floor, a sweeping counter and a menu that features fried chicken, chicken-shrimp fish boxes, Poorboys (double-decker burger) and milkshakes

www.wagnerspharmacy.com; www.theparkette.com.

2. Old Louisville

Louisville grew up on the Ohio falls, where travellers disembarked for the rapids. It's where Lewis and Clark set off for the Pacific and was once home to meat-processing, distilling and barrel-making industries. West Main Street sports the most iron-facade buildings outside of New York's SoHo district while Old Louisville — especially at St James's Court, Belgravia and Central Park — features street upon street of fine Victorian mansions (no two houses, no two porches, appear the same), some with gas lighting. The more bohemian Germantown, Butchertown and Smoketown, and the Highlands area flanking Bardstown Road, feature post-civil-war pastel-painted "shotguns" ("fire a shotgun through the letterbox into the garden and you won't hit a wall"), "camelbacks" (shotguns with a second storey at the back) and "double-barrel shotguns" (homes sharing walls). For some literary and criminal history, visit the Old Seelbach hotel, a setting for the Great Gatsby and where Al Capone would dine and escape the cops through a secret door (the now not-so-secret door is still there). Download a self-guided walking map at www.mainstreetassociation.com.

www.seelbachhilton.com

3. NuLu New Louisville

Wrecked by prohibition and blighted by 1960s redevelopment, Louisville is a town steering a clever course between old and new, its historic downtown is fast regenerating and looking to an arty, trendy and ecofriendly future. Whiskey Row is now Museum Row, with the 21C hotel, the Mohammad Ali Centre, the Louisville Slugger Museum (home of the fabled baseball bat — you can't miss it, there's a six-storey-high bat outside), the Frazier History Museum and the award-winning interactive Louisville Science Centre. For art, head to East Market and East Main (visit FirstFridayTrolleyHop.com to see what's new). Galerie Hertz offers contemporary art, as does the Art Ecology Gallery and the Green Building Gallery, housed in a stunning eco-building. The area is fast becoming a foodie haven too. Try Social 732 (Green Building) for "American tapas" with a gastropub feel or The White Oak, where food and art collide, tastefully, at the smart Artemisia Gallery.

4. 21C Museum Hotel

Voted America's best hotel by Conde Nast Traveler's readers, the 21C Museum is a 91-room luxury boutique hotel and art gallery set in five historic warehouse buildings on West Main Street. Billed as "North America's first museum dedicated solely to collecting and exhibiting contemporary art of the 21st century", it has its own art curator and arts foundation and the sweeping gallery space in its lobby atrium features work by New York photographer Andres Serrano, Brit Sam Taylor-Wood and Nigerian-born Turner Prize-finalist Yinka Shonibare. It is owned by Kentucky philanthropists and art collectors Steve Wilson and his wife, Laura Lee Brown, both prominent sponsors of the ground-breaking Ali Centre.

www.21cmuseumhotel.com

5. Mohammad Ali Centre

It took a long time for the city to honour its most famous son, the "Louisville Lip" but the $80 million (Dh294 million), state-of-the-art Mohammad Ali Centre was worth the wait. An interactive museum, it is the first cultural space in America dedicated to the man widely regarded — not least by himself — as the greatest of all time. You can shadow-box with Ali and have his boxer daughter Laita teach you dad's shuffle, in the ring. But best of all, grab a ringside seat for Ali's most dramatic bout — the Rumble in the Jungle against George Foreman in 1974 in Zaire — rerun, on video, in its entirety.

www.alicenter.org

6. Bluegrass

Bluegrass is Kentucky's official state music and Bill "Big Mon" Monroe's Blue Moon of Kentucky, along with Stephen Foster's My Old Kentucky Home, are the official state songs. Both drop the perfect soundtrack for driving through the rolling pasturelands of, er, Kentucky bluegrass and the eastern Appalachian mountains, where the scenery shouts BANJO, albeit with a twang! Bill Monroe pioneered the genre in the Forties with his Bluegrass Boys, playing speeded-up banjo and fiddle-led, foot-tapping country music, which drew on traditional Celtic and English music brought over by the Protestant Irish (the Scotch-Irish, as they say here). There's live bluegrass music at The Bluegrass Brewing Company in Louisville and the annual River of Music Party in Owensboro in July, featuring bluegrass legends such as Doc Watson and Lance LeRoy. For background on all things bluegrass, visit the International Bluegrass Music Museum at Owensboro.

www.bluegrass-museum.org

7. Keep Louisville Weird!

Adopted from the highly successful Keep Austin Weird campaign established to fend off the march of conglomerates and promote small businesses in Austin, Texas, so Louisville has managed to retain a refreshingly chain-free metro area, with scores of indie boutiques, bookstores, bars and restaurants. For vintage clothes at retro prices, try Nitty Gritty on Barret Avenue. Next door is Deal selling "mid-century furniture" (translation: 1950s). Have lunch and refreshments at the mad but family-fun Lynn's Paradise Café. For a local dive bar, head to the Nachbar in Germantown, with live music and an international beverage menu.

www.keeplouisvilleweird.com

8. Scenic drives

Lexington's horse country boasts endless vistas of rolling grass hills, with manicured stud farms criss-crossed by white fences or dry-stone walls, dotted with old barns and steepled wooden baptist churches, all presided over by the colonels' mansions. The Old Frankfort Pike is perhaps best, an undulating, 30-mile twisting drive on smooth, empty roads through quiet countryside which bursts into life in spring with redbuds and cherry blossom. At Midway stop for "sides and soups", burgers and pies in the clapperboard railway station, the Wallace Station Deli Bakery. Queues punch through the door at lunch and if you can't park in a booth or a bench, head out back (looks like a charming pub garden). Bizarrely, for the dearth of traffic, there's a lot of roadkill — so much so you can't help but play "roadkill bingo": Tick off the possums, squirrels, racoons and deer as you go. It's game over when you see a dead skunk, with windows and sunroof open.

www.wallacestation.com