Win, Place, or Show: Rating Kentucky Derby Parties at Chicago Bars

While I’m delighted to know that people outside my hometown of Louisville find the Kentucky Derby exciting enough to celebrate, even hundreds of miles away, I’m skeptical as to what outsiders think a Derby party looks like—and today’s Cinco de Mayo bashes haven’t exactly eased my anxiety. Premixed Mint Juleps? No thank you…

While I’m delighted to know that people outside my hometown of Louisville find the Kentucky Derby exciting enough to celebrate, even hundreds of miles away, I’m skeptical as to what outsiders think a Derby party looks like—and today’s Cinco de Mayo bashes haven’t exactly eased my anxiety. Premixed Mint Juleps? No thank you. Also, please note: There is a fine line between a garish Derby getup and an elegant trackside ensemble. Seersucker suits are not a joke; on the flip side, Kentucky is not a landlocked Martha’s Vineyard.

After receiving an avalanche of e-mails promoting Kentucky Derby parties at Chicago bars this Saturday, May 7th, I decided to hold a little race of my own and sent a questionnaire to several local watering holes. Who wins by a nose? Take a gander at the field, which I’ve scored by horse lengths, Derby-style:

 

REAL-LIFE DERBY EXPERIENCE

Bull & Bear: Laura Faith, the bar’s director of marketing and production, says: “We went every year in college and sat in the infield for the total action. It was not the classiest but definitely action-packed.” The infield is no grandstand spot on Millionaire’s Row, but it’s fun in a nudity-welcomed/Mardi Gras kind of way. (+ 1 length)

Frontier: Nope, says Charlie Barrone, Frontier’s general manager. (- ½ length)

The Pony: General manager John Gurgone has been to the infield “for the past couple of years. One year, it rained all day, and the infield turned into a huge mud fight!” Oh, dear. (+ ½ length)

The Red Canary: Owner Jamie Uhlier has also sat in the infield. (+ ½ length)

South Branch: One of the bar’s owners, Nate Hilding, has been twice: once in the infield and once with a seat in a skybox—highfalutin! (+ 1 ½ lengths)

 

MINT JULEP EXECUTION

Bull & Bear: Woodford Reserve signature Mint Juleps for $9. (+ 1 ½ lengths)

Frontier: Agave Mint Juleps for $6 (an interesting-sounding twist); Grandstand champagne cocktails also $6. (+ 1 length)

The Pony: Maker’s Mark Mint Juleps for $5. “We’re using a down-home Kentucky recipe with fresh mint.” (+ 1 length)

The Red Canary: The classic version (bourbon, simple syrup, mint, and soda water), plus a variation named after the legendary 1920s horse Man o’ War, who never won the Derby but ran his heart out just the same; $5 each. (+ 1 length)

South Branch: The bar will be serving several drinks named after past Derby winners: the Smarty Jones Julep, plus the Manhattan of War, Mine That Old Fashioned Bird, and Secretariat’s Apple; $6 each. (+ 1 length)

 

PARTY FAVORS

Bull & Bear: Two guests will win limited-edition Kentucky Derby bottles of Woodford Reserve. (+ 1 length)

Frontier: “We will have tons of programs on hand for the day,” Barrone says—downloaded from the Internet, mind you, not originals. (+ 1/2 length)

The Pony: Official Derby glasses listing all past winners and Maker’s Mark Derby hats. (+ 2 lengths)

The Red Canary: “Wish I would have thought of that,” Uhlier says. (- 1 length)

South Branch: Custom South Branch Derby programs, with unique Derby cover art, a classic racing form inside, and the lyrics to . . . (+ 2 lengths)

 

PLANS FOR THE CHASER’S FAVORITE DERBY DAY MOMENT, THE SINGING OF “MY OLD KENTUCKY HOME”

Bull & Bear: “I’m sure we can make some arrangements,” Faith says. (+ 1/2 length)

Frontier: N/A (“Whaaat?” moans The Chaser.) (- 2 lengths)

The Pony: “Our DJ will definitely lead the bar through the song.” (+ 1 ½ lengths)

The Red Canary: “We’ll be playing it!” (+ 1 length)

South Branch: The lyrics will be printed in the bar’s custom program, and a DJ will play bluegrass and Kentucky-themed music throughout the party. (+ 3 lengths)

 

DRESSING THE PART

Bull & Bear: “Derby dress encouraged: flowing summer dresses, oversized hats, seersucker pants, polos, croakies, and boat shoes.” Croakies? The Chaser thinks not. (+ 1 length)

Frontier: “We’re encouraging patrons to pull out big hats and seersucker suits.” (+ 1 length)

The Pony: Winners of the Best Dressed and Best Hat competitions will win $100 each. (+ 2 lengths)

The Red Canary: Sundresses, linens, and headwear for both sexes are encouraged (we assume the sundresses part is for women). (+ 1 length)

South Branch: Prizes will be handed out for Best Dressed and Best Hats; the staff will be outfitted in Derby attire. “The men will resemble cast members from the movie Seabiscuit,” says general manager Bart Vivian. (Multiple mentions of “floppy hats” for ladies worries The Chaser. Hats should be sculptural works of art.) (+ 2 ½ lengths)

 

A LEG UP

Bull & Bear: Betting cards let partiers pick their favorite horses for the chance to win prizes. (+ 1 length)

Frontier: Chef Brian Jupiter is making chicken-fried steak with “all the fixins.” Note: The Chaser considers country ham on butter buns a more authentic Derby protein but cannot deny the appeal of chicken-fried steak. (+ 2 lengths)

The Pony: The party is a fundraiser for Equestrian Connection, which serves people with disabilities through therapeutic horseback riding. Also, The Pony is a University of Kentucky bar. (+ 3 lengths)

The Red Canary: The Red Canary’s leafy patio reminds The Chaser of the paddock where they parade the horses at Churchill Downs—a biggie, since being stuck inside all day is not very Derby. (+ 4 lengths)

South Branch: The party is a fundraiser for Friends of the Chicago River. (+ 2 lengths)

 

POST TIME (LOGISTICS ONLY: NO POINTS AWARDED)

Bull & Bear: The party will be in full swing from 5 to 7 p.m.; arrive early for your best shot at a seat. No cover.

Frontier: Starts at 11 a.m., no cover.

The Pony: Starts at 11 a.m., no cover, $10 Southern buffet.

The Red Canary: Starts at 11 a.m., no cover.

South Branch: The party runs from 3 to 8 p.m. Tickets are $12 and include a Southern-style buffet.

 

THE CHASER PLACES HER BET

Win: South Branch. Custom programs? Great idea.

Place: The Pony. It’s a Kentucky bar. It’s embarrassing if they don’t do Derby well.

Show: The Red Canary. If the weather’s good, this bar could edge closer to the wire.

Fourth: Bull & Bear. Woodford Reserve is a Chaser favorite.

Also ran: Frontier. But it’s their first-ever Derby party, so they’re still a little green.
 

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