The Gambler 500 is an annual event started by Tate Morgan with his friends in 2014. The original idea was a race between friends where they took $500 cars and saw how far they could travel offroad in Oregon. Today, it has evolved into an event with thousands of participants from around the world who take all sorts of vehicles, and build them in ways you would never think of. Gambler Town, the “homebase” of the event, holds live music, a huge car show, camping, racing, and more activities. The event’s main purpose is to participate in a public land clean up, where participants explore the public or national lands around wherever it is held. This year, 220,000 pounds of trash, a dozen RVs, 15 cars and a boat was cleaned up from the Crooked River National Grassland outside of Madras, Oregon, over the span of two days.
One of the custom Gambler cars showing off during the car show in Gamblertown. The Gambler 500 was held on the weekend of June 27 in Madras, Oregon with thousands in attendance.
Photo Gallery: Gambler 500
Andreas Shypertt, Photographer
July 14, 2025
Gamblers surrounding the stage to hear the founder of the event, Tate Morgan, speak about the weekend and give out awards. The Gambler 500 was held on the weekend of June 27 in Madras, Oregon.
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