Historic Festival 44 welcomes Donald Osborne, ASA, as a Special Guest this Labor Day Weekend at Lime Rock Park.

An automotive expert, accredited senior appraiser, and one of the most engaging storytellers in the collector car world, Osborne has built a career around helping people understand not just what cars are—but why they matter. Whether advising collectors, evaluating historically significant automobiles, or bringing stories to life on screen, his perspective is rooted in knowledge, curiosity, and a deep appreciation for the art of the automobile.

That appreciation began early.

Growing up in New York City, Osborne didn’t come from a car-owning family. Instead, his introduction to the automotive world came through books and magazines—hours spent studying Road & Track and AutoWeek, absorbing everything he could. His first auto show, at the New York Coliseum in 1964, left a lasting impression. Even at a young age, he was drawn not to the familiar, but to the distinctive cars like the Citroën DS, Lancias, Abarths, and, most notably, Alfa Romeos.

That early fascination became a lifelong connection.

As Historic Festival 44 celebrates Alfa Romeo as its Featured Marque, Osborne’s presence carries special meaning. His admiration for Italian design—where engineering meets artistry—has shaped both his personal passion and professional work. From the elegance of coachbuilt bodies to the racing heritage embedded in the brand, Alfa Romeo represents something enduring: performance, beauty, and emotion in equal measure.

“It seems I cannot recall a time that I have not had a great passion for Alfa Romeo, and the opportunity to drive and own many examples of the marque has only increased that feeling. Alfas are, and will always be, very close to my heart!”

Osborne’s career has taken him across every corner of the collector car world. As the principal of Automotive Valuation Services, he has advised collectors on acquisitions, correctness and market positioning, often serving as a trusted set of eyes for cars located across the United States, Canada and Europe. His philosophy is simple—understand the client, understand the car, and bring the two together with clarity and confidence.

Donald Osborne participated in the Mille Miglia in 2015 driving a 1956 Alfa Romeo Giulietta Sprint. His drive is part of a long-standing appreciation for this historic event, which he has participated in multiple times.

Beyond consulting, he has become a familiar presence to enthusiasts through his television work and collaborations with fellow car collector Jay Leno, where his knowledge and enthusiasm have helped bring automotive history to a broader audience.

He is also a respected voice in concours judging and curation, serving in leadership roles with major automotive events and institutions, including the Audrain Automobile Museum. Recently named FIVA North America Representative, his approach remains consistent: cars are not static objects, but living pieces of history shaped by design, competition, and time.

Donald Osborne in his 1950 Crosley Gardiner Special at HF22 in 2005—a fitting nod to Crosley’s unlikely competition history, including a nearly stock Crosley Hotshot that went on to a class win the inaugural six-hour endurance race at Sebring International Raceway in 1950.

“For me, the icing on the cake of this weekend is being back at Lime Rock Park, where I first learned to drive a car on a track at a Skip Barber session and spent many days here as a member of the VSCCA, as a corner worker, in race control and behind the wheel in a race car. Lime Rock is very much my ‘home track’”

At Historic Festival 44, Osborne will join a distinguished group of guests and participants as Lime Rock Park once again becomes a gathering place for some of the most significant historic race cars and automotive stories in the world.

His presence adds another layer to a weekend defined by heritage, performance, and the people who keep these machines—and their stories—alive.

For tickets and more information on Historic Festival 44, click here.