The hats... the stars... the betting... the scene...

...and then there's the race

Email|Print| Text size + By Tina Cassidy
Globe Staff / February 1, 2004

LOUISVILLE, Ky. -- My trip to the Kentucky Derby last spring began in a Boston millinery studio. The hat had to be special, and I settled on a coral-colored, wide-brimmed topper, trimmed with horsehair and ribbon, a creation the hat designer said she would contort in the back as a final flourish.

"It's all about the exit," she said.

As if on cue, I'm on a US Airways flight from Boston, hurtling toward Kentucky via Charlotte, N.C., with my hats -- I am going to need more than one for all the parties and the Kentucky Oaks race the day before the Derby -- stuffed in the overhead bin.

It was on the Charlotte to Louisville leg when the excitement kicked in. Hatboxes replaced laptop cases as the carry-on item of choice among those joining the flight. I was seated next to a guy who said -- in a Brooklyn accent as thick as his gold bracelet -- that he was headed straight for the VIP area at Churchill Downs. He called himself Ira, wore a sparingly buttoned Hawaiian shirt, said he had named a horse Meadow Soprano, and pulled out a wad of $50 and $100 bills to buy Bloody Marys for the women sitting around him. We were all strangers, but not for long. After one drink, the women were already comparing hats. One passenger had sewn bar essentials -- nips of Jack Daniel's, etc. -- onto her straw number.

The Derby was shaping up to be the spectacle that devotees said it was, and it was only Thursday morning, two days before two of the most exciting minutes in sports.

In fact, with attendance regularly hitting 150,000 on race day, the merriment surrounding the Kentucky Derby extends for days before and after the event. Wednesday night: Bob Dylan concert downtown. Friday, brunches and betting at the track for the Kentucky Oaks, an event that used to be populated by locals but has become just as big a deal as the Derby, with men and women dressed to the nines and drawing on mint juleps well before noon.

There are art shows, festivals, and a Six Flags hulking on the horizon, offering so much to do that you realize it's no sprint to the finish line, it's a marathon.

When it comes to walking, pace yourself. When it comes to drinking bourbon, pace yourself. When it comes to eating Derby Pie, pace yourself. When it comes to placing bets, pace yourself. Because come Derby Day, your feet will be sore, you'll be hung over, bloated, and broke -- and you'll be loving every minute of it.

Forty-five minutes after stepping off the plane, I was at the finish line at Churchill Downs, where on Thursdays it costs just $2 to get in. Attendance was light and we could stand at the rail petting horses as they walked by from the paddock, something children, and a few grown-ups, were delighted to do.

I scanned a program and picked a horse named City Desk, ridden by Jerry Bailey, a living-legend jockey. The air was perfumed with cigar smoke and in a flash, I went from feeling like a winner to becoming a certified loser. On the next race, a horse with 10-to-1 odds stole the show. This must be why mint juleps are so necessary here.

It was a great introduction to the next two days of racing because the Downs was not yet packed with people. There were no lines for the restrooms; it was easy to get a program listing all the race statistics; and you could move around the park freely without security guards making sure you had the right ticket to proceed beyond a certain point.

Later that night, at a hotel known to be a prerace hangout, we spotted jockey Gary Stevens, who played George "The Iceman" Woolf in the movie "Seabiscuit." Stevens was riding Atswhatimtalkinabout in the Derby, and he confidently doled out a tip: His horse would win the Run for the Roses.

Feeling privileged to have this information, we decided to leave. On our way out, we noticed that the hotel's hat shop was still open despite its being nearly midnight. The boutique was almost as crowded as the bar, with women squealing as they tried on monstrous creations: one with ostrich feathers followed by another with tulle and beading followed by a big straw number with a giant bow.

The next morning, we got dressed as if we were attending a British wedding. Hats, dresses, heels, lipstick. Over brunch at a friend of a friend's, we fortified ourselves with country ham, biscuits, and grits and headed to the Downs, already packed by 11 a.m. In fact, the Oaks will draw a crowd as big as 120,000 people, just shy of Derby Day attendance.

"It's become a phenomenon in its own right," Redmon Lair, a deputy secretary in the state cabinet that oversees the racing commission, said moments after entering the park.

Indeed it has.

Thursday night offers the biggest party, which last year was packed with the likes of Kid Rock, Anna Nicole Smith, Troy Aikman, and Tara Reid. The black-tie party, hosted by the twin sisters who used to be in the Doublemint gum commercials, draws so many celebrities and gawkers to the leafy residential street where one of them lives (the other lives in LA) that police have to put up barricades. Tickets are $500 each and the proceeds are earmarked for charity. The party is private, and by invitation. Christmas-style lights set up on the rolling lawn clinch the carnival atmosphere.

Saturday morning, we dress up all over again -- dress, hat, pumps --and head to the historic Pendennis Club, which claims to have invented the old-fashioned, for more country ham, biscuits, and grits amid a sea of seersucker suits. Then everyone piles onto a bus, the best way to get to the Downs because the hackneys receive preferential lane treatment (in other words, no traffic), and sings "My Old Kentucky Home" along the way. The main parking lots fill quickly and many residents who live around the Downs will let you park in their yards for about $20. On our way in, we notice two things. First, there are tickets to be had -- at face value. Apparently the scalping laws are strict here. Second, local custom -- completely illicit -- dictates that you must smuggle alcohol into the track. In fact, one year, an able-bodied woman rode a wheelchair in, hiding bottles of bourbon under her legs. So in the parking lot, well-heeled, proper Southern women stuff bourbon nips into their cleavage. It's all part of the spectacle.

One of the first people we spot after passing through the security checkpoint is Ivana Trump. She's standing next to Susan Lucci, who's standing near the guy hawking mint juleps in collectible glass cups (the equivalent of Mardi Gras beads here) for $7, the way they sell Budweisers at Fenway.

The rest of the day goes something like this: Stand in line to place wager. Watch the race. Lose. Eat. Drink. Pick out a hat in the crowd to discuss. Repeat.

Things start to get more focused just before the big race. The air is electric. The call to post blares and the crowd noise -- think Gillette Stadium during a playoff game times two -- reaches a fever pitch. Then they're off. And they're moving so fast you can't tell which horse is which. Doesn't matter. Women teeter on chairs, men choke on their cigars. Beverages go flying. Then a nose breaks the finish line. On this day, it's a horse that wasn't on anybody's radar screen, Funny Cide. The race's reputation for derailing favorites proves true. Handicapping seems a futile science.

All the more reason to focus on the hats.

Tina Cassidy can be reached at

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