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The Kentucky Derby's majestic image as one of America's premier sporting events—to say nothing of its reputation as being decadent and depraved—is well deserved. The 11th race at Louisville's Churchill Downs on the first Saturday in May (in 2011, it's May 7), Derby is almost as well known for big hats, mint juleps, and hometown boy Hunter S. Thompson's first foray into gonzo journalism as for being the United States' premier horserace. But the Derby experience in Louisville doesn't stop at Churchill Downs's finish line. Whether you're visiting The 'Ville for the run for the roses or at any other time of year, here are five ways to get more out of "the most exciting two minutes in sports," gonzo style.
5… At the track
Since it opened 137 years ago, Churchill Downs (700 Central Ave., 502-636-4400, www.churchilldowns.com) has run the Kentucky Derby, now the first leg of the triple crown of thoroughbred racing. The Kentucky Oaks, the marquee race held the day before Derby and featuring fillies, offers almost the same pomp and circumstance. Oaks Day use to be the big draw for locals, but its increase in popularity has made the Thursday before Derby the go-to race day for many Kentuckians.
Also popular are Friday night races throughout the spring and fall seasons (generally a week before Derby through July 4th weekend and late October through late November)—if you go, know the typical attire falls in between the big hats and seersucker suits of Derby and the jean shorts and tank tops of Thursday mornings at the track.
Among the more important things to keep in mind is not to buy the mint juleps at Churchill, where they cost $9 and can be weak; instead head downtown after the track and try them out at the Brown Hotel's ornate Lobby Bar (335 W. Broadway, 502-583-1234, www.brownhotel.com). And if the libations inspire you to bring home a souvenir, know that you can find the commemorative Derby glasses on the cheap all over town. Almost any day there's racing at Churchill you have a good chance of seeing three-time Derby-winning jockey Calvin Borel on a mount at his home track. Churchill merits a visit even if the track is dark: year-round it's home to the Kentucky Derby Museum ($13).
4… At the tables
While you'll have a difficult time finding horse meat in Louisville, plenty of restaurants have connections to the sport of kings—and not in that cheesy NASCAR cafe sort of way. Wagner's Pharmacy (3113 S. 4th St., 502-375-3800, www.wagnerspharmacy.com), an 89-year-old drug store across the street from Churchill's backside, attracts jockeys and horsemen to its lunch counter (a scene in "Secretariat" also was filmed here). Those Derby-winning horses pictured on the walls? They're former colleagues to some of your fellow diners. Food like patty melts and burgers are what you expect from a greasy spoon, but you'll be hard pressed to find another pharmacy that sells jockey silks.
On the other end of the dining spectrum there's Jack Fry's (1007 Bardstown Road, 502-452-9244, www.jackfrys.com), a cozy upscale steakhouse in Louisville's Highlands neighborhood. Its connection to horse racing lies not with the jockeys or horsemen, but rather with the gamblers: its namesake and original owner was bookmaking (and bootlegging) out of the back room in the 1930s. The restaurant's extensive list of wines by the glass provides plenty of pairing options for its traditional steakhouse entrées.
3… At the stables
Kentucky didn't become home to America's premier horse race out of happenstance. Soil in the state's bluegrass region is high in protein and minerals, causing horses that graze there to be stronger. Louisville is just on the cusp of the area; to get to the marquee stables, you'll need to make an hour's drive east through rolling farm country, where that thoroughbred grazing just off the road very well may be a retired or future Derby winner. Lane's End (1500 Midway Road, Versailles; 859-873-7300; www.lanesend.com) offers tours on Thursday mornings at 10 a.m. except during the breeding season (approximately February through mid-July) and its January, September, and November sales (although there's no reason you can't pose as a prospective buyer). It's most famous resident is Zenyatta, the 2010 horse of the year who retired with a 19-1 record after losing by a head in last year's Breeders' Cup at Churchill Downs. WinStar Farm (3001 Pisgah Pike, Versailles; 859-873-1717; www.winstarfarm.com) is the home of Super Saver, the winner of the 2010 Derby. It gives public tours year round on Mondays, Wednesdays and Fridays at 1 p.m. Feeling down seeing horses living a posher life than you, even if they have earned more money? Treat yourself to a hearty sandwich before returning to Louisville at the nearby Wallace Station Deli and Bakery (3854 Old Frankfort Pike, Versailles; 859-846-5161; www.wallacestation.com).
2… At the stills
In addition to strong horses, what's in the ground has made Kentucky world famous for its bourbon: its superior whiskey results from a limestone aquifer that adds calcium to the water, which mixes well with yeast. Woodford Reserve's distillery (7855 McCracken Pike, Versailles; 859-879-1812; www.woodfordreserve.com; $5) reflects both pursuits. One of six distilleries on Kentucky's Bourbon Trail, Woodford Reserve is the official bourbon of Derby and is used in the $1,000 mint julep sold at Churchill around race day to raise money for charity (ingredients vary each year, but have included mint grown near the Euphrates River, organic sugar from Australia and ice from the Arctic Circle). If the hour-long tour that features the only copper stills used in a bourbon distillery and the longest barrel run in the United States—topped off by a few samples—doesn't quench your thirst for bourbon knowledge, Woodford Reserve also offers day-long academies ($150). Held about once a month, master distiller Chris Morris leads you through a primer on bourbon, a series of tastings, and a tour. A gourmet lunch also is included.
Back in Louisville, Brown-Forman, which owns Woodford Reserve, offers tours of its cooperage in collaboration with Mint Julep Tours (866-986-8779, www.mintjuleptours.com, $59, reservations required). The white oak barrels manufactured here also are used by Jack Daniel's, Old Forester and Early Times (the whiskey used in Churchill Downs's mint juleps).
1…At the inns
If you're planning to visit Louisville on Derby weekend, reserve your room early or you'll be vying for space in a manger (which also can be booked that first weekend in May, with all the horses in town). With North America's first museum devoted exclusively to 21st century art and the chic restaurant Proof on Main on its first floor, downtown's boutique 21c Museum Hotel (700 W. Main St., 877-217-6400, www.21chotel.com) attracts celebs and high-rollers for Derby weekend. Stay at 21c almost any other weekend though and you'll get the same luxury experience but at a more affordable cost (leaving you more money to gamble at the track). And if you're all ponied out, 21c is near museums for two of Louisville's other sports icons: Louisville Slugger (800 W. Main St., 502-588-7228, www.sluggermuseum.org, $10) and Muhammad Ali (144 N. 6th St., 502-584-9254, www.alicenter.org, $9).
On Derby Eve 1889 Jesse James's outlaw brother Frank stayed at what's now Bashford Manor Bed and Breakfast (2227 Bashford Manor Lane, 502-295-9005, www.bashfordmanor.com); the next afternoon he turned $5,000 into $55,000 on the 10–1 Spokane. Four years later, this former thoroughbred racing and breeding farm owned the Derby-winning horse, Lookout. (Some fella name Lincoln visited here too, but alas it was 35 years before Churchill Downs opened and it's a safe bet he wasn't too fast on a mount).