Derby Day

A Harbor View hat parade and ‘the most exciting two minutes in sports.’


It was a dark and stormy night in Louisville for a muddy 144th running of the famed Kentucky Derby, but it was a beautiful sunset evening at the Harbor View Hotel, with nary a raindrop to be seen. The 40 or so guests at the Harbor View party roared with excitement during the 1¼-mile race when the 3-year-old colt Justified shot far into the lead in the deep stretch to win this first leg of the fabled Triple Crown in 2 minutes, 4.2 seconds. But the Martha’s Vineyard festivities before the race were just as entertaining.

Upon entering you could sidle up to the bar for, besides the regular offerings, one of two signature drinks, the traditional Mint Julep or, in honor of Cinco de Mayo, a Highland Cup, concocted of chili-infused tequila with cilantro, fresh lime, topped off with club soda, and served over shaved ice. You could snag delectable Derby-inspired hors d’oeuvres created by Executive Chef Richard Doucette as waiters went around, or you could visit the elaborate fruit-and-nut-decorated cheese table at your leisure. DJ Bluto (a.k.a. Jarrett Campbell), who does the hotel’s parties and special events, kept the place lively with upbeat music that didn’t intrude upon the animated conversation.

But hands down it was the visual array of colors, patterns, and designs that were the most delightful entertainment. The Kentucky Derby is a wonderful excuse for ladies to express their inner Southern belle, adorned in their spring fashions. The big question of the evening was whether the women chose their headgear or outfit first. With only one exception, it was their festooned bonnets that the women began with in putting together their ensembles. A table of seven ladies who all knew each other since childhood had dubbed themselves the “Fabulous 55 Tour” because they were there to celebrate on May 5th the fact that they all were turning 55 years old this year. When posed the question, they all cried, “Hats first!” Asked what was the deciding factor for their ultimate decision, there were cries of “color,” “style,” “size,” and finally, “a glass of wine!”

At another table, Jeanne Madormo and Eileen Clanci, who’d been friends for 26 years, came to the Vineyard for this year’s annual getaway. They found out about the party on the hotel’s website, and decided it would be a great place to celebrate the Kentucky Derby. The Vineyard had been on their bucket list for years.

A foursome of two couples, Sasha and Dough Ruggieri and Michelle and Scott Milne, had also come for the weekend. They loved the Harbor View because it “had such a vintage feel, and we felt it would be fun. It was a last-minute decision to come, and we’re so glad to be here.” Sasha had bought her hat in town that day, while Michelle’s was a genuine antique she’d acquired some time back. The men were wearing fedoras and splendid complimentary, Derby-appropriate attire. Other guests, some local and some additional visitors, wore pastel-colored suits, or bold separates that coordinated with their Derby headwear and accessories.

If you happened to come unadorned, Tania Tilton and Stephanie Rossi of Dreamboat Hats provided plenty of distinctive, wide-brimmed and veiled hats decorated with flowers, feathers, beads, bows, and ribbons in many colors from which to choose to express your inner creativity.

For men, they offered bow and neckties, and pocket squares for the extra-dashing gentleman. The sisters had done a lively business in the hotel’s lobby earlier that day, and plenty of the guests tried on their displayed offerings, particularly the smaller fascinator, a small, lightweight ornamental headpiece that fits on the head using an Alice-band-type base, or even a small comb or clip.

Bets were called in after the race, and the party wrapped up around 8 pm, by which time everyone was fully sated from “Derby Madness 2018.”