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We Went to the Gambler 500. It Was Awesome.


What is the Gambler 500? That’s kind of like asking what the meaning of life is. The response is kind of complicated, but overall actually very simple. Essentially, the Gambler 500 involves navigating vehicles to and from waypoints over about 500 miles. It’s not a race. It’s not a competition. It is, however, an awesome time.


The Gambler 500, which brought in 744 official entries, started from Portland Meadows racetrack and wound its way through highways, back roads, and forest service trails across northwest and central Oregon. The goal? To have a great time.

WARN Cherokee
The WARN recovery Cherokee

Warn was the official recovery sponsor, and thus, I brought my 2001 Jeep Cherokee, equipped with a WARN ZEON 8-S,  Epic hook and Epic shackles, and full recovery kit, in case we had to help some Gamblers back onto the trail. We did have some WARN employees take part in a Lincoln Continental, Volvo 240, Subaru Legacy, and a Ford Explorer.

Kevin’s Volvo 240 Gambler 500 entry. Kevin is an engineer here at Warn.

Gambler 500 organizers suggested you will have more fun in a lower-priced oddball vehicle than a built up 4×4. Many people took that advice as there were scads of highly customized, low-dollar vehicles including things like subcompact Subaru Justys and Ford Festivas; scads of cheap, old AWD Subarus; cut-up Ford Crown Victorias; mountains of ancient minivans; and several vehicles we’d throw into the land yacht category. We also saw no fewer than three lifted limousines and one articulated city bus with a hot tub in the back. No lie. We have pics below to prove it.

Lifted Limo at Gambler 500
One of several lifted limos. This one has a straight axle swap up front, WARN Premium Hubs, and a 460 V8 under the hood.

Whether it was tackling the Barlow Trail on Mt. Hood, rolling down the highway towards Bend, Oregon, or zooming through the forests near Hoodoo, everyone had a great time and lent a helping hand to those who broke down.

The end point for day one was the parking lot at Hoodoo Ski Area outside of Sisters, OR. There we camped, conversed, and had an awesome night. Then it was back on the road in the AM for day two.


At the end of day two, Gamblers met up again at Portland Meadows that evening for The Final Waypoint, where there were bands, food, and drinks waiting. We had a booth, and even gave away some product, including a WARN VR8-S.

WARN Booth at Gambler 500

The Gambler organizers awarded the WARN VR8-S to the “recovery hero.” This was the person who was the most helpful out on the trails, too.

Winner of the WARN VR8-S winch at the Gambler 500.
The winner of the VR8-S winch. He and his Hummer were instrumental in helping others on the trail during the event.

While we didn’t personally pull anyone out of a ditch, we did help a Subaru straighten out an A arm on the trail. He’d hit a large rock and the vehicle was immobile. I hooked my ZEON 8-S to strap and shackle, and with the help of a big hammer and huge wood block, we were able realign the control arm. This got the driver back onto the trail so the rest of the pack could get by. Rumor has it he was able to get to town that evening, get another control arm, and “gamble” the next day!

Winching a Subaru's A Arm.
Getting set up to help straighten out a bent A arm on this Subaru so we could get the owner back onto the trail.

The whole thing isn’t just one big rolling rally, either. There was a competition to see who could pickup the most trash along the trails and shooting pits. A total of 30 yards were brought in, which included the massive amount of shells you see below.

Picked up shell casings

Additionally, several Gambler cars were auctioned off, with 100% of the money raised going to the Children’s Cancer Association—$3,200 total. Now that’s doing some good!

Crazy cars, crazy cool people, and a crazy good time. The Gambler 500 proved to be awesome, and we look forward to gambling again in 2018. Until then, as organizer Tate Morgan would say, “always be gambling,” and here are some more photos.

“Stinkbug” from the guys at the Off Road Podcast.
Behold: The Blue Waffle!
Yes, you’re seeing correctly. This is an articulated city bus. It may or may not have had a hot tub in the back.
You saw a little bit of everything at the Gambler 500, including Tom’s Explorer. Tom is a product manager here at Warn. The Honda wagon is also on point.
Corolla on mud tires? You betcha!
These guys helped to pick up a ton of trash during the event, including a ton of shell casings. They were rewarded with a new AR15. Great job, and nice beer bottle costume, sir!
Toyota Hilux diesel with a WARN bumper and winch
This messaging should’ve been standard on all entrants. Bonus for WARN decal.
Speed Racer’s other ride …
Long travel Miata driven by Jessi Combs!
Mustang on mud terrains? Uh huh!
Three out of four fenders ain’t bad.
This M8274-equipped 6×6 Pinzgauer was gambling!
Now this WARN-equipped VW Rabbit is a hatchback we can really get behind!
One of several Suzuki Samurais at the event. This one had an M8 winch, too.
Pake’s Lincoln Town Car, complete with roof-mounted bathtub. Pake is a machinist here at Warn, and he had an VR winch on a Multi Mount.
Chevy Tracker dog wagon
The Shaggin Wagon has met it’s match. Under all that fur is a Chevy Tracker.
Gambler Ford van
Truly vantastic.
Volvo S60
WARN-equipped Volvo. No, we don’t offer that mounting system.
Another fine WARN-equipped rig. Apparently this one is a six cylinder, automatic, as evidenced by the stickers. Note the two spares. #GOPREPARED!
It wasn’t 4WD, but who cares: this Toyota van was rad.

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