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Kentucky itineraries

I returned home to my family, with a determination to bring them as soon as possible to live in Kentucky, which I esteemed a second paradise, at the risk of my life and fortune.
– Daniel Boone

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Little Black Book

Kentucky Derby: Lexington Essentials

by Aimee Lynne

Kentucky Derby: Lexington Essentials
And they're off! Photo: boboroshi / Flickr

The famous horse race isn't the only thing to do in Kentucky. Artist and designer Aimee Lynne gave us the Louisville-to-Lexington lowdown.

LEXINGTON, Kentucky – I'm a transplanted New Yorker living in Lexington, Kentucky. My birthday is May 5. It falls on Kentucky Derby day often, which results in a love/love relationship with the races.

THE SCENE

Once or twice a season, I go to Lexington's race track, Keeneland, which runs throughout April. I wear a nice dress, have lunch in the dining room, and sit in a friend's box. Boxes and membership are reserved primarily for horse owners. The Keeneland Clubhouse is a treasure with beautifully preserved interiors. The bathrooms on the second floor are fitted in crisp green-and-white wallpaper from the 1960s. The attendant in charge wears a perfectly starched uniform, hands out drying cloths and mints, and always helps with an odd zipper.

Keeneland is even prettier than Churchill Downs, home of the Derby. (Sorry, Louisville!) That's why they filmed most of Secretariat here. But the Derby and the Oaks are the coveted tickets. I've been three times, and each was completely different. (One was a nightmare. I can laugh at it now, but DON'T GO TO THE INFIELD. It is like Frat Week in Panama during spring break.) There are a million and one fabulous charity parties the night before Derby, and you just need to keep your ear to the ground to figure those out.

Kentucky racing really is a treat. The weather is gorgeous, the crowds are spirited but civil, and you get to wear heels and drink juleps and old-fashioneds. Last summer, I went to the races outside Stockholm and, though the track was pretty, it was nothing like the beauty of the Bluegrass.

Jockeys

THE BEST BETS

My betting style confirms I am the least reliable person to ask for a tip of the day. My strategy: a) put three dollars on a pretty horse that has a nice, high bum 2) or a jockey with the best colored silks or 3) bet according to the craziness of the name. No, I don't ever win because I still don't understand the furlong, trifecta, or odds, but that is the joy of it. Everyone tries to teach me, but I don't want to learn.

WHERE TO STAY

I love the 21C, a fine art hotel. They have a great collection and a great curator, so the rotating shows though small are internationally important. And they also have a great restaurant I love, Proof. The other charming hotels in Lexington are Seelbach Hilton and The Brown Hotel.

WHERE TO EAT

Regarding food, fitting it all in and going to the races is impossible. There are many fantastic restaurants down here, but these are the ones I'd prioritize. Jack Fry's is a trusty standard with great steaks, old photos on the walls, and fantastic ambience. Rye is the brand-new restaurant that everyone is talking about. Lilly's serves a fantastic lunchtime burger, has a sunny atmosphere, and is convenient for exploring the small shops on Bardstown Road. 610 Magnolia specializes in delicious, all-organic, and mostly local food and terrific wine pairings. And I can't wait for St. Charles Exchange, the chic new restaurant opening in May. (My friend David McGuire, who wrote Fathom's Derby Diary, is one of the founders.) Table Three Ten is a chic spot that serves the very best casual upscale bistro fare. Pastry chef Stella Parks was voted one of Food & Wine's best new pastry chefs of 2012.

Science Hill

WHAT TO DO

Visit Wolford Reserve
No one should come all this way and not go to Woodford Reserve for a tour. It's a short drive, but you have to rent a car anyway to get around, so why not?.

Buy Old Things in Shelbyville
if you're interested in antiquing, stop in Shelbyville. Making Ends Meet is three full floors of gorgeous bolts of discount designer textiles and trims, but you have to be on a mission or you will get sucked in and never come out. (Their trim room is like heaven.) The sandwich shop around the corner, McKinleys Bread Shop & Deli, serves the best pimento cheese on white bread for next to nothing.

If you are shopping with the ladies, a good tea lunch treat is Science Hill, an old historic girls school that's now houses the Wakefield-Scearce antiques gallery (one of the bigger antiques shops in the area), an inn, and a restaurant that serves outstanding Southern comfort food. My order is fried chicken with green beans drowned in butter, mashed potatoes, and apple crisp cobbler.

Have a Midway Meal
For a true taste of old Kentucky, have a meal at Holly Hill Inn, located in an historic old mansion in Midway. Chef Ouita Michel, an avid Kentucky culinary and cultural historian, excels in her use of locally grown produce and locally raised meats and dairy.

Have an Arty Drink
Once I'm food-and-fabric'd out and nearly down for the count, I'd rally and head back to 21c for one (okay, several) of their special cocktails like Hard Thyme at the very white long marble bar. Don't miss the little portraits in the bar. They're great and modern and, though there are hundreds, each feels unique. And it's nice to recognize the subjects, like Jim Gray, Lexington's current mayor and huge art collector.

On the way to the 21C bathrooms, be sure and catch your shadow projected large on the wall by the elevators. It's a true attraction: an amazing, large wall with a video work called Text Rain by Camille Utterbach and Romy Achituv. Everyone stops for photos of scrolling "raining" letters that move with you.

Derby Hats

Hit the Road
Louisville to Lexington is a scenic, hour-and-a-half drive past along US 60. You'll pass gorgeous horse farms whose formerly all-white fences are now painted black (but are no less glorious), Old Frankfort Pike, Keeneland Racetrack, and the famed Calumet Farm. For another beautiful road trip, take route 25 north of Lexington to Iron Works Pike and the Kentucky Horse Park.

THE ESSENTIAL ACCESSORY

What have I left out? Of course, the hats! You want a fabulous one, because that's what Derby is for as far as I'm concerned. Dee's has them, as does the Kentucky Museum of Arts and Craft. I'm in love with an Etsy shop that carries fascinators made by hand in Copenhagen by Flora Amelie, so I'd arrange my outfit according to what she's got going. And that's about everything.

BUT WAIT, THERE'S MORE

My Derby Diary
Little Black Book: The Master Blender's Derby Circuit

Photos in story, from top: David Paul Ohmer / Flickr; Courtesy of Science Hill Inn; L. Burchfield/ Flickr

Aimee is an artist and designer (and New Yorker!) currently living in Lexington, Kentucky. She travels for the simple reason that the only place that could be better than where she is now is where she is going next.

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