For the last week or so, our collective social media feeds have been clogged up with delightfully elegant photos of vintage racing cars, unbelievably rare collector cars, and some truly inspiring concepts, all in impeccable condition. Every August since 1950, car collectors, spectators, and connoisseurs of all things fancy have been gathering in the tiny beach town of Monterey, CA for what has become known as the Monterey Car Week.

The week is packed with vintage races at the nearby Laguna Seca Raceway, cruise events, and concludes with the legendary Pebble Beach Concours D’Elegance, where the 200 finest collector cars in the world compete to see which one is the best of the best. Serious congratulations go to Bruce McCaw and his stunningly gorgeous 1929 Mercedes-Benz convertible for taking this year’s coveted Best of Show award.

Additionally, several auction houses hold car sales which consistently set records with their staggeringly high gavel prices earned by some of the finest collector cars in the land. While perusing the result sheets, I noticed that the auctions were largely devoid of off-road vehicles, save for a funky little 1970 Meyers Manx offered up by Southeby’s.

This got me to thinking: what do you do if you’re a fan of vintage vehicles but you’re also really into off-roading? Certainly, driving in the dirt is not a new concept so there has to be vaguely historically significant vehicles designed around these ideals and are, theoretically, sound financial investments.

Undeterred, I jumped over to everyone’s favorite internet auction site, eBay Motors, to see what I could turn up. While I wasn’t able to find anything nearly as extravagant as the 1956 Aston Martin DBR1 that took the podium at Nürburgring in 1959 and went on to change hands for a cool $22.5 million at Pebble Beach last week, I did stumble on a few neat old off-roaders that are certainly worthy of adding to one’s collection.

Military-Spec Off-Road Collector Cars: 1942 Dodge WC52

This particular example is looking fairly rough but the seller seems fairly confidant in the condition of the engine internals but not so much with the brakes. These trucks were manufactured by Dodge for the military during WWII and came in various configurations, with this one being a ¾ ton model fitted with a sort of wooden pickup bed that appears to have gone rotten. Weighing in at around 5,550 lbs. and motivated by a 99 hp inline six with the valves in the block, these things weren’t exactly quick. Nonetheless, with a two-speed transfer case and a massive winch on the front, they aided the allies with their second World Championship by handling duties too substantial for the Willys MJ and requiring more finesse than the M4 Sherman could muster.

Upon returning from the war, enough servicemen noticed a general lack of all-terrain utility vehicles on the market and started saying things like, “Hey, those WC’s were the bee’s knees. I wish I had one for my [insert manly trade] business.” Dodge listened and brought this model to the market as the legendary Power Wagon, which led to the development of the 4×4 D-series pickup, which led to the Ram pickup as we know it today. Now you can order up a new Ram 2500 Power Wagon with a heated steering wheel, a motorized sunroof, and a touch screen on the dash that displays apps from your smart phone. Oh, how times have changed.

The Original Off-Road Collector Cars: 1948 Willys-Overland CJ-2A

On the other end of the condition spectrum, this particular Jeep was rescued from a field and treated to a rather thorough restoration over a period of some time. While a post-war civilian version, this one has been finished in olive drab with (I assume) Army-spec markings on the hood to give it that “ready to storm the western front” appeal. A fun rumor about the early models is that, due to a design flaw in the steering linkage, they had a terrifying habit of pulling hard to the left under heavy braking, however retrofitting a link from a later model is said to correct this. Hard braking is, of course, relative as these early Jeeps were powered by a 60 hp flathead four banger and weren’t geared very tall.

Introduced in 1945, the Willys-Overland CJ-2A is interesting in that it was the first regular-production, civilian-spec Jeep (Jeep, by the way, was only a nickname at that point). Developed from the venerable MB series that was the runabout of choice for generations of GI’s, the CJ (for “civilian Jeep”) was also the general public’s first taste of a mass-produced 4×4 vehicle, with the above-mentioned Power Wagon going on sale shortly thereafter. The CJ line soldiered on through several generations and parent companies until it was replaced by the Wrangler some 41 years later. With a legacy like that, it’s no surprise that they’ve developed a status as collector cars. The vehicle is so iconic that the design of the vertical grill slats with adjacent round headlights is a trademarked design. ollllo for life!

Alternative Off-Road Collector Cars: 1964 Toyota Land Cruiser FJ45

Hailing from across the western pond, this Toyota pickup is exceptionally rare in North America despite being based off of the popular FJ40 SUV. It is, in fact, a US-spec model and seems to have only managed to accumulate a little over 28,000 miles in its 53 years of service. Aside from an older repaint and some fresh upholstery work, this truck remains largely original and an awesome investment on that fact alone. Not that mileage is a huge deal on these things as the GMC-derived F-series inline six that powers them can easily take ten times that mileage with proper maintenance. Being an early 4×4, however, its interior appointments are comically Spartan and there isn’t a whole lot going on in the safety department. Speaking of safety, you’ll notice that the fuel tank is located under the seats so an early FJ’s may not be the best collector cars for someone who is a heavy smoker.

Yet another WWII derivative, legend has it that when the Imperial Japanese Army occupied the Philippines, they found an allied Jeep and sent it home for reverse engineering. While the resulting prototype was completely different from the production version, it was the design of the original military Jeep that set the ball rolling for the first Japanese off-roader and Toyota’s longest-running nameplate. The Land Cruiser evolved into its own product line, offering multiple shapes and sizes with the 40-series shown here carrying on into the eighties. Stateside, our current Land Cruiser selection is limited to a large and luxurious Range Rover alternative but overseas, there are several models offered, including the Land Cruiser Prado which is the basis for our Lexus GX as well as sharing the basic chassis with the FJ Cruiser. The classic FJ40, though, was the model that put Toyota on the map as a producer of some of the most durable trucks on the planet. There’s a reason why the Land Cruiser is the official car of “I own several thousand acres of wildlife preserve in a third-world country. Care to take a tour?”

Gentlemen’s Off-Road Collector Cars: 1966 Land Rover Series IIA

This one isn’t as old or early production as some of the other trucks we’ve looked at but I wanted to include something from Europe and I couldn’t find a Series I or an old Unimog. Nonetheless, this one isn’t that much different from the original model aside from a slightly longer wheelbase and an updated powertrain. It’s also equipped with the optional Tropical Roof which diverts airflow to vents installed into the ceiling of the car. Normally, I’m a little leary of older British vehicles with holes in the roof but this one seems to be in Albuquerque so I doubt it’s had much of an opportunity to experience rain leaks. It also appears to be largely original, with just enough of that survivor patina that collectors adore and lets you know that it’s been treated to a healthy maintenance regimen without any heavy restoration work. Personally, I always dug the hood (bonnet?) mounted spare wheel but I wonder how much it hinders getting at the engine since it’s old and British and you’re going to be in there a lot.

Much like the other vehicles on this list, the OG Land Rover traces its roots back to the years immediately following WWII as well as the original, military-spec Jeep. In post-war Europe, hoards of Jeeps were left behind by the US and many of them rode out their retirement serving farm duties. Unlike the United States, most of England was busy trying to rebuild itself so construction materials like steel were scarce and heavily rationed. In the meantime, the Rover car company was looking to drone up some cash to re-start their luxury car production in the wake of their factory being bombed. Conceived to bridge the functionality gap between a tractor and a Jeep, the first prototype rode on a MB Jeep chassis and featured a power takeoff fitting to run agricultural equipment. The production version, however, featured a unique and fully boxed frame and an aluminum body to circumvent the steel shortages. It stayed in production, receiving evolutionary updates, through the mid-80s when it was replaced by the Defender. It, however, was effectively another update to the original line and that car stayed in production until last year. It also served military duty for many armies as well as the UN. It’s success ultimately afforded the development of the upmarket Range Rover so the next time some pumpkin latte-slurping suburbanite cuts you off in a Rangie, you have the Land Rover Series trucks to thank.

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