OWLS HEAD — The Pine Tree Jamboree makes its museum debut September 11–13, entering a new chapter at the Owls Head Transportation Museum in Owls Head, Maine. The three-day event celebrates the craftsmanship, ingenuity, camaraderie and racing traditions surrounding early hot rodding and flathead-powered vehicles.

Pine Tree Jamboree is a period-correct celebration of traditional hot rodding, flathead-powered vehicles, vintage racing traditions and the community surrounding them. Beginning in 2026, the event is hosted at the Owls Head Transportation Museum in partnership with Traditional Speed and Custom, LLC.

The event highlights two- and four-wheeled flathead-powered vehicles from 1953 and earlier, with an emphasis on authentic, period-correct builds. Throughout the weekend, visitors can experience the sights, sounds and atmosphere of a traditional vintage racing gathering while exploring the Owls Head Transportation Museum’s collection and interactive exhibits.

"Pine Tree Jamboree is about more than the cars—it celebrates the people who build them, the history behind them and the community that keeps these traditions alive," said an OHTM news release. "Bringing the Jamboree to Owls Head creates an opportunity to connect this unique automotive culture with the museum’s mission of preserving and sharing transportation history. At its heart, the Jamboree is a collaborative celebration rather than a competition, with no prizes on the line, just the opportunity to participate, connect and earn some bragging rights."

A Weekend of Vintage Racing and Hands-On Activities

Pine Tree Jamboree offers a full weekend of activities for both participants and spectators. Friday includes technical inspection and time trials, while Saturday features a full day of racing traditions. Sunday brings vintage auto cross competition and an awards ceremony.

Beyond the track, visitors can explore a variety of activities throughout the weekend, including:

● Flathead-powered vintage vehicles and hot rods

● Vintage racing traditions and demonstrations

● The Hot Rod Teeter-Totter Challenge

● Swap meet

● Vintage car rides

● Biplane rides (weather-dependent) 

● Interactive exhibits throughout the Owls Head Transportation Museum

● Opportunities to meet drivers, builders and fellow enthusiasts

● Comedy show & music at Friday night’s Welcome Party

Friday Night Welcome Party Features Live Music and Comedy

Pine Tree Jamboree weekend officially kicks off Friday evening, September 11, with the Welcome Party, an evening of live music, food, drinks and comedy at the Owls Head Transportation Museum.

The evening begins with Clyde Bisbee & The Wheelhouse Revelers, performing from 6 - 7:30 p.m. The band brings together swing jazz, western swing and era-inspired music, setting the tone for a night celebrating the sounds and spirit of an earlier era.

At 7:30 p.m., the evening shifts to comedy featuring Mitch Stinson, Tony V and headliner Jimmy Dunn.

Mitch Stinson, a former U.S. Navy aircraft-carrier aviator, brings stories drawn from his military aviation career and transition to civilian life. Veteran Boston comedian and actor Tony V has appeared in television and film productions including Seinfeld, The Town, The Heat and Rescue Me. Headliner Jimmy Dunn is known for his role as “Moose” on Paramount+’s Frasier reboot and appearances on Conan, The Late Show with David Letterman, and Comics Come Home.

Food and a cash bar will be available during the evening.

The Welcome Party is an 18+ event. Separate tickets are required for the Welcome Party, and admission is not included with Pine Tree Jamboree event admission or museum membership. Welcome Party tickets are available separately for $25 in advance and at the door while space permits.

This event is made possible with additional support from Wisscasset Speedway. For tickets, schedules and additional event information, visit www.owlshead.org.

Owls Head Transportation Museum is a nonprofit educational organization dedicated to collecting, preserving, exhibiting and operating historically significant aircraft, ground vehicles, engines and related technologies. Through its collection, exhibits, educational programs and special events, the museum connects visitors with the evolution of transportation through hands- on experiences and opportunities to explore the people, technology and ingenuity behind it.