Meet Lilly Pray: Our 2025 Chief Judge for the Hilton Head Island Concours d'Elegance & Motoring Festival

We’re thrilled to announce that the 2025 Hilton Head Island Concours d'Elegance & Motoring Festival will be graced by the one and only Lilly Pray, our Chief Judge! With over two decades of experience in the world of concours judging and a deep passion for all things motoring, Lilly brings unparalleled expertise and an infectious enthusiasm to our event. Here’s a glimpse into the fascinating story behind our esteemed Chief Judge.

A Passion That Started in the Garage

Lilly’s love for cars didn’t begin in a boardroom or a classroom—it started in the garage, with her father, Malcolm Pray, a noted collector from Greenwich, Connecticut. Growing up, Lilly learned the ropes of the car world from the best. Whether she was lending a hand working on his collection or accompanying him to concours events, her fascination with classic and vintage cars was clear from the start. If you wanted to find Lilly as a child, you’d have to head to the garage where the magic happened.

Her early exposure to the world of concours d'elegance shaped her path and led her to become one of the most respected judges in the U.S. For 24 years, Lilly has judged at some of the most prestigious automotive events across the country, and now, she’s bringing her wealth of knowledge, passion, and energy to our festival!

Not Just a Judge—A True Car Enthusiast

Lilly isn’t just a judge—she’s an owner and passionate driver of many vintage cars. Whether rain or shine, you’ll find her cruising "topless" in her beloved convertibles, embracing the freedom that comes with the open road. As a true enthusiast, Lilly has a keen eye for what makes a car truly special, and that’s exactly what we’re excited to have her bring to the Concours d’Elegance & Motoring Festival in 2025.

A Career with Heart and Service

Beyond her car passion, Lilly’s professional career is equally inspiring. As a Registered Nurse at Boulder Community Health, she specializes in Emergency, Orthopedics, and Neurology. But her journey didn’t start in healthcare. Lilly spent over 20 years in the fire service, engineering fire trucks and serving as a Firefighter/Paramedic. Her commitment to helping others didn’t stop there—she also volunteers with the Boulder Police Department as a Victim Advocate.

Her spirit of service extends to her involvement with several boards, including the Turtle Invitational, the Russell Maguire Foundation, and the Malcolm Pray Achievement Center. Through these organizations, Lilly works to guide and inspire young people, helping them to chase their dreams and find their own path to success.

A Family Affair

Lilly’s love for cars is a family affair. She shares her passion for vintage vehicles with her 25-year-old daughter, Portia, who is also a concours judge at many prestigious events. Together, they enjoy driving classic cars, hiking in the mountains, and soaking up time by the sea. It’s clear that motoring runs in the family’s veins!

From Her First Car to Her Favorite Ride

Lilly’s first car may not have been a speed demon, but it holds a special place in her heart. It was a 1973 Audi diesel—an unremarkable car in terms of speed (with a 0-60 time measured in days), but it was her introduction to life on the road. In fact, Lilly started driving at just 10 years old in the family’s 1968 Dune Buggy. The Dune Buggy wasn’t just a fun toy; it was a family heirloom of sorts. Over the course of 40 years, Lilly’s father taught four children and five grandchildren to drive in that very car. Today, that Dune Buggy is on display at the Malcolm Pray Achievement Center, a tribute to the many cherished memories it helped create.

As for Lilly’s favorite car? That honor goes to her 1959 Porsche Convertible D, affectionately known as “Alfred.” She’s owned Alfred since 1996, and the car has been a loyal companion, bringing Lilly countless miles and smiles. Whenever she’s out on the concours show field, she can’t help but remember the sage advice her father gave her all those years ago. His influence is still with her every time she takes the wheel.

Why We’re Excited to Have Lilly as Our Chief Judge

We couldn’t be more excited to welcome Lilly Pray as our 2025 Chief Judge for the Hilton Head Island Concours d'Elegance & Motoring Festival. Her lifetime of experience in the car world, her dedication to service, and her unbridled enthusiasm make her the perfect leader for this prestigious event. We’re sure that under her watch, the 2025 festival will be an unforgettable celebration of motoring excellence.

Be sure to join us and experience the excitement, passion, and Southern hospitality that Lilly, and all of us, are proud to share with you!