5 Old Pickup Trucks That Are Worth Serious Money Now

Everybody wants a cheap pickup truck, but here's the thing, they're extremely hard to find — even the cheapest pickup trucks on sale today all cost north of $30,000. The problem is that we as consumers demand too much from trucks today. Everything has to offer two rows of comfortable seating, the latest in technological wizardry, and it has to handle as well as the sedans, hatchbacks, and SUVs it's ultimately replacing. Wind the clock back a few decades and, as long as it had a practical bed and perhaps an AM radio, you were good to go.

While you might think that buying an old and simple truck would be heaps cheaper, as it turns out, some of those old-time favorites are now worth pretty much the same as brand-new models, if not more. That's because collectors now scramble to find rare examples that have escaped the trappings of hard work. This article explores five such models. We sourced the prices from a variety of reputable third-party resources, and we arranged the trucks from oldest to newest.

Some of these trucks are worth serious money, due to their obscurity and exclusivity, while others are poster models with loads of performance goodies from days gone by. Either way, all are probably more expensive than you may expect, and several command sums north of what you'd pay for a new '25 base model Maverick with 0 miles on the odometer.

The classic Hudson is a truck that fits into that obscure and exclusive category we mentioned above. It was actually a pretty capable pickup for the time, equipped with 14-leaf rear and 10-leaf front springs, a ¾-ton rating, a seven-foot bed, plus a sturdy, reinforced chassis. The Hudson was more than just a smart sedan with a bed grafted onto the back, it was a genuinely well-engineered product.

Power came courtesy of a 212-cubic inch engine, which fed 96 hard-working horses exclusively to the rear wheels. Later models sported a 6 horsepower advantage, and two wheelbase options were available. Buyers could opt for the standard 117-inch version or the 124-inch Big Boy. Yes, it really was called that — perhaps the best name a pickup has ever had, aside from Dodge's Li'l Red Express.

If this slick pickup from almost 90 years ago takes your fancy, then prepare to delve deep into your wallet. You may also need to wait a while, as they're exceptionally rare. Classic.com – a site that collates auction data from around the world — shows us that it's not unusual for smart examples to command figures north of $50,000. Sure, it might not boast Apple CarPlay or adaptive cruise control, but it certainly looks cool, and you're unlikely to come across another.

This brutish pickup truck certainly leans on the heavier-duty side of things. Dodge built the original Power Wagon from 1946 to 1968. While many older trucks are fit only for lugging small loads or for polishing up and parking at local car shows, the Dodge Power Wagon Type-D — also known as the Military Type or Flat Fender Power Wagon, thanks to its wide, flat wheel fenders and broad running boards — was built tough and engineered to last. So, even in 2025, the pickup is perfect for getting some serious work done.

When it first debuted, Dodge dubbed the Power Wagon as "the truck that needs no roads," which speaks volumes about this gargantuan pickup's capability. It was also one of the first four-wheel drive trucks on offer, but where it falls short is its engine — a humble inline-six. As you can easily imagine, plenty of enthusiasts have upgraded the Power Wagon with larger engines over the years, and it's these customized examples that can really command the big bucks. While, according to Classic.com, a stock model in good condition typically fetches between $50,000 and $100,000, modified examples can cost north of $250,000. The original Power Wagon, therefore, is a prime example of an old pickup truck worth serious money in 2025. It may be one of the more practical options, too. Well, more practical for hard work, that is — we're not sure how ideal it would be for a highway commute or for zipping around city centers. 

Hailing from the famous Task Force series, the Apache 3100 was produced during the last half of the 1950s, and when it comes to looking good, these are some of the most stylish classic trucks available on the market anywhere. The chrome-clad pickup trucks are very much products of their era in the sense that they look fabulous, although their tech is very much out of date. However, their simple construction and spacious engine bays make the Apache 3100s prime candidates for the resto-mod treatment, adding things like luxury interiors, fancy paint jobs, and powerful engine swaps.

Models in good condition can cost upward of $45,000. However, for a sharp resto-mod with heaps of power and plenty of modern conveniences, you can easily spend triple that figure. Earlier this year, we asked our readers what they thought the best-looking pickup trucks ever sold were, and the Chevy Apache earned a well-deserved spot. So, while a modern truck might be more practical and capable, the timeless style of a '50s Chevy is always in vogue, even if it costs a pretty penny to make one yours. 

The GMC Syclone is another old pickup truck that's worth serious money in 2025. Imagine being able to tell someone you drive a Syclone. That's worth the financial outlay alone. However, it's not just the name that's cool, as the Syclone hails from an era in which performance trucks were just finding their feet. As such, there was a 280-horsepower, 4.6-liter turbocharged V6 under the Syclone's hood. Those angry American horses were sent to all four wheels, albeit with a 65% rear bias, which surely encouraged a little lunacy on wet roads. That's some serious firepower for an old truck.

It's pretty easy to see why someone would want to own a Syclone, but, sadly, the barrier to ownership is quite high. Classic.com shows that the average sale price at auctions during the last five years was just over $45,000, with models in exceptional condition commanding figures in the region of $100,000 and beyond. Sure, the Maverick Lobo might be a beast, and buying one of those would be a lot cheaper, but would it be half as cool?

As far as old pickup trucks go, this one is pretty special. While it doesn't sport chrome bumpers or pre-date the seatbelt, having first arrived in the 2004 model year, this beast is now over 20 years old. 

If you're unfamiliar, the Dodge Ram SRT-10 paired a regular or quad-cab Dodge Ram truck with an 8.3-liter Viper-sourced V10, which kicked out an astonishing 500 horsepower. However, only the regular cab models were equipped with six-speed manual transmissions, so that's where you want to put your money. After all, if you're buying a 500-horsepower V10 truck, why not go all out and get a stick shift?

A quick perusal on Bring A Trailer reveals that the desire for these trucks is quite high right now, with prices sitting around $40,000 to $70,000 for a well-maintained model with average miles. Ignore the fact that this will net you a very nice Ram truck with 0 miles on it in 2025, because the truth is we may never see a truck like this produced again.