Big Hats, Bigger Fun

Pequot Library's Derby Day, 2024

By Jessica McEntee | Photos by Jarret Liotta

Q: What beloved Fairfield County program features al fresco revelry, fascinators, and colorful tailgates?

A: Pequot Library’s beloved Derby Day Celebration, a fundraiser dating back to 2008. Derby Day attracts upwards of 600 partygoers, many of whom show up in flossy attire. Pastel-hued sundresses and seersucker suits abound, and each year sees at least one bright jockey outfit.

The library’s volunteer judges, neighbors Marlene Sheehan and Butzi Moffitt, confer Best Dressed awards to a lady and a gentleman. Last year’s ladies winner Olivia Charney donned a showstopper outfit: a fuchsia pantsuit with ruffled sleeves. Her coordinating foot-tall fascinator called to mind an abstract peony surrounded by undulating feathers in varying shades of pink. Other guests take a less traditional approach. One local musical legend/stalwart library supporter came dressed in a beige linen three-piece suit with a white silk flower boutonniere and a humble straw hat. His wife, also a world-renowned musician, sported an elegant broad-brimmed black hat topped with a coral silk ribbon.

Marlene and Butzi also give an award for the category of Best Tailgate. Tailgates have been part of the scene straight out of the gates (apologies for the bad pun). In the early years, this meant participants paid extra to park their cars on the library’s expansive Great Lawn, and they propped open their trunks for serving cocktails and nibbles. As the event evolved, tailgates have become increasingly creative, with some groups planning months in advance. Last year’s winner showcased a nautical theme with an actual Sunfish sailboat and a hand-painted sailcloth. This group converted the cockpit into an ice trough. Other years have seen a Veuve Clicquot theme with life-sized chess pieces in the signature golden hue; carved ice sculptures (a horse’s head and a frozen luge for delivering shots); a Lily Pulitzer tent straight out of Palm Beach; and walls of faux roses set against boxwood greens. Some tailgaters set up lawn furniture to create chic outdoor rooms. The prevailing mood is a friendly one in spite of the competition, and guests can travel from tailgate to tailgate, mingling and making new friends. They can also enjoy food and cocktails set up in a central tent. In recent years, guests can also choose from two bar carts that serve mint juleps plus signature cocktails.

The main tent houses a silent auction for one-of-a-kind experiences such as an evening cruise from Southport Harbor and a jaunt in a private plane. Guests can also purchase mystery bottles from a bourbon wall and vote for their favorite horses, as true betting is a no-no. Inside the library’s historic auditorium, a large TV broadcasts the race. Finally, Derby Day draws local sponsors eager to capitalize on this lively crowd. Funds raised during this lovely event provide crucial support for the library’s annual operating budget. Put May 3, 2025 on your calendar and come see the magic for yourself!

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