Win the 1948 Willys Jeepster Sweepstakes!
- $2518 Entries+8 Promo
- $5040 Entries+16 Promo
- $10090 Entries+36 Promo
- $200200 Entries+80 Promo
- $500650 Entries+260 Promo
- $7501150 Entries+460 Promo
- $1,0001750 Entries+700 Promo
- $2,0004000 Entries+1600 Promo
Enter to Win a Classic!
Your Chance to Own a 1948 Willys Jeepster Convertible
Cruise into summer with timeless style! One lucky winner will take home this beautifully restored 1948 Willys Jeepster—finished in rich burgundy with gleaming chrome in all the right places. A smooth-running 4-cylinder engine and “three-on-the-tree” column-shift manual transmission make every drive a nostalgic joyride. Pop the top on sunny days and enjoy open-air motoring the way it was meant to be.
Originally introduced after WWII, the Willys Jeepster blended rugged Jeep heritage with the flair of a postwar convertible. Only 10,326 were built in 1948, and surviving examples like this one are rare treasures of American automotive history. Willys-Overland, second only to Ford by 1912, built this beauty as a symbol of peace, prosperity, and good old-fashioned fun.
Don’t miss your chance to win a piece of true Americana—a classic convertible perfect for summer drives, car shows, or just turning heads on Main Street. Enter now and make this Willys Jeepster yours!
- $10,000
- Close DateFeb 16, 2026
- Close Time11:59 PM EST
- Drawing DateFeb 25, 2026
- Drawing Time12:00 PM EST
- Drawing LocationOwls Head Transportation Museum
Flash Contest Winners
Illuminating the rich history of transportation's earliest pioneers and technologies!
For 50 years, the Owls Head Transportation Museum has been a premier vintage automotive and aviation destination, serving communities throughout New England with education and entertainment that ignites America's passion for the science of transportation.
Owls Head Transportation Museum has emerged as an experiential learning center in Maine, for teaching science, technology, engineering and mathematics (STEM), where visitors, exhibitors, students, teachers and volunteers can share their knowledge, tools, experience and designs — and participate in creating transportation innovations for the future. OHTM offers educational programming, camps and outreach activities throughout the year.
OHTM welcomes more than 40,000 visitors each year to explore an unprecedented collection of more than 1,000 rare and restored ground vehicles, aircraft, bicycles, motorcycles, engines, and artifacts. OHTM offers the largest operational antique vehicle collection in New England, with onsite workshop facilities that turn regular maintenance activities into unique learning opportunities. Offering year-round family programs, OHTM is dedicated to curating interactive experiences for visitors of all ages.