Kentucky Derby Party in Fire Island Pines: A 30-Year Tradition

2023 Derby Hat contest winner Chris Mai (left, as Mary Poppins) with husband Matthew Markoff
Kentucky Derby Hat Winner 2023, Chris Mai with with husband Matthew Markoff.
Photo by Mike Borowski.
IN REAL TIME: Attendees at Sip N Twirl watching a live broadcast of the Kentucky Derby on the nightclub’s center screen.Photo by Mike Borowski

Spring is in the air and so is the Kentucky Derby this weekend! Businesses are reopening, the Harbor’s cherry trees are flowering and the ferry schedule keeps expanding. Another major sign of the new season is its first big-themed event: the annual Derby Party, which is being held on Saturday afternoon, May 4 at Sip N Twirl.  Featuring a live, nail-biting telecast of the Kentucky Derby (“The Most Exciting Two Minutes in Sports”), the celebration will feature partygoers dressed to impress for its increasingly competitive hat contest.


Hosted by beloved resident drag queen Bubbles d’Boob, it also features a raffle to benefit the Fire Island Pines Chamber of Commerce.  (Full disclosure: yours truly is a resident Pines DJ and spins this party each year.)


“As the first official party in the Pines, it’s so fun to see everyone showing up in full force,” enthused Bubbles to me. “Everyone loves a dress-up party, and the variety and creativity here in the Pines is astounding.”


This year’s race will be its milestone 150th and is the first leg of horse racing’s Triple Crown.  The Pines edition itself has an over three decades history, stretching back to the early 90s,  when former resident, the late Allan Masur (fondly remembered for founding our community’s Congregation B’nai Olam,) began the yearly tradition as a private party at his Bayfront home.


But when Masur passed away in 2005, the party was on the verge of being lost forever.  Pines businesses owner and longtime resident PJ McAteer, President of the FIP Chamber of Commerce, kept it alive. It was his idea to move the event the following year to his then-recently purchased club Sip N Twirl, where it’s continued since.


“I love this community and my priority is always to preserve its traditions,” McAteer said.  “The Derby party is extra special, not only because it’s the kickoff to the new season, but because it brings together homeowners, renters and visitors of all ages.”


In addition to rooting for this year’s odds-on equestrian favorites Fierceness and Sierra Leone, what else can you expect?  Mint juleps will be flowing, while a free buffet will feature tasty faves like Bourbon Meatballs and Brown Kentucky Sliders.


Cutie ginger bartender Rich Heaton reveals his secrets for the perfect mix: “Don’t over-muddle the mint, and best over crushed ice.”


Stay tuned for more Kentucky Derby coverage in Fire Island Pines as well as neighboring Fire Island communities. The 150th Kentucky Derby takes place Saturday, May 4, 2024 with coverage beginning at 2:30 p.m.

As for tips on the perfect Derby “Lewk,” we turn to last year’s Derby Hat winner: Chris Mai, who dazzled in a spot-on recreation of Mary Poppins’ full outfit at the races. Here are his three suggestions for making a splash:


  1. “Dress it Up! Go for an upscale, traditional look. When do you get to dress up nowadays?


  1. “Get creative. Think of your Derby Hat like a school diorama on top of your head. Choose a storyline and build your hat. Super Glue, Gorilla glue and Duct Tape are your best friends here!


  1. “Go Big! What about a full costume? Think of the context of the Derby and any relatable references that you can attach to the theme. Go obscure and get your creative juices flowing!”


And we’re off!  The party kicks off this Saturday at 5 p.m., with race post time scheduled for 6:57 p.m. There will be no cover charge at the door. Enjoy!