The Kentucky Derby – you may have heard – is decadent and depraved. So too shall you be. Here's your guide to proper parties, proper attire and (most importantly) how to squeeze a couple of bucks out of this thing.

  • Maysville
    17 W. 26th St.
    b/t 6th Ave. & Broadway
    (646) 490-8240


    Maison Premiere

    298 Bedford Ave.
    b/t S. 1st & Grand St.
    (347) 335-0446

    The Parties

    NYC newcomers Maysville have deep Bluegrass State love – the ceiling’s a glowing vellum relief map of the Kentucky town for which they're named. On Saturday they’ll park a massive BBQ smoker out front to dish out rib plates and pulled pork alongside $8 juleps while the race is projected large format on the resto’s wall.

    Meanwhile, in Williamsburg, absinthe-and-oyster specialists Maison Premiere will be serving up eight specialty juleps made with a litany of house-made syrups, bitters and Four Roses bourbon. And at MP you don’t watch the Derby, you listen: the race is broadcast old-school via vintage radio.

  • J. Press York Street

    304 Bleecker St.
    b/t Barrow St. & Grove St.
    (212) 255-6151

    The Gear

    Two goals with derby duds: be the guy who doesn’t look like he’s wearing a costume, and get stuff you’ll actually wear again. Your three must-have items from J. Press York Street, the West Village collab between the legendary prepsters and designers du jour Ovadia Brothers:

  • Twin Spires

    $2 and up
    twinspires.com

    The Wagers

    Vice advice courtesy Richard Eng, official handicapper/columnist for The Las Vegas Review-Journal and author of Betting on Horse Racing for Dummies (that would be you).

    Know the Odds
    Seventeen of the horses will have double-digit odds. Two horses that have a good chance to run well: Normandy Invasion, 12-1, and Goldencents, 15-1.

    Bet Across the Board
    straight bet (win, place or show) is $2. So a $2 across-the-board bet on any one horse is $6.  To build a betting bankroll, pool your money with friends. You can add more long shots while spreading the risk.

    Vet the Ponies
    If a horse finished 1st or 2nd in a Grade 1 final prep race (which means they ran very well) but still has high odds, he’s a smart long shot bet.

    Sleep Well
    Should you make it down to Dixie, stay at The Brown Hotel. Richard's been to 15 Derbies and swears by it.