Are you itching to get out to the weekend car show and swap some stories with your pals? Do you want a new project for your garage? Explore some unique choices for the best classic pickup trucks on the market. We’ve highlighted a special truck from each decade that helps to tell the story of the automotive industry and evolving car culture.

1926 Ford Model T Convertible Pickup

While the standard Model T was designed as a simple two-person transport, adding the pickup box turned it into a more functional member of your home or business. There is no mistaking the iconic early design with wood wheels and high suspension. This baby will always be a hit at the parade!

1931 Ford Model A

After the proven success of the Model T, Ford rolled out the Model A in 1927, and they continued to fly off the factory floor until 1931. With more than five million produced, it remains a viable option for modern-day rat rodders and custom truck enthusiasts. If you love cars, you will recognize their large sculpted front fenders and high nose from local classic car shows and museums.

1948 International Harvester

Early versions of the pickup had a hard time competing with teams of draft horses in hauling goods to market. The 1948 International Harvester serves as a hallmark in a more robust design ready for heavy hauls around town. Its frame grew out of the post-war experience while the half-moon white walls, brush guards, and the six-cylinder engine makes a strong show at the mill.

1955 Chevrolet 3100

If you ever watched a cops-and-robbers Saturday matinée in the 50s, the good guys were likely piloting a Chevrolet. The 3100 pickups featured that same oversized nose, muscular wide fenders, and a 180-horsepower V8 small block. The big engine enabled its roomy bed to haul more products while the cab left plenty of space for three workers.

1960 Chevrolet C10

Drivers of pickup trucks in the 60s wanted a ride that looked more like their family sedan and less like something parked at the depot. The 1960 Chevrolet C10 delivered on that desire in spades. Its wide square grille sported a pair of wild eyebrows that doubled as marker lights. Long fenders lent it an air of elegance. At the same time, the long-wheelbase option served up a full eight-foot bed. While future generations would lose that wild grille design, the rest of the C10 set the stage for the next 40 years of light-duty trucks.

1972 Jeep CJ-5

After the end of WWII, the General Purpose vehicle left the army, but it kept rolling off factory floors and earned the brand name Jeep. For decades, it served as a rugged little workhorse, best suited to off-road exploration. Come 1972, the Jeep CJ-5 earned international recognition as the ride driven by Mindy on the TV show Mork and Mindy. And now everybody wants one! It is still a popular classic car due to its indestructible nature and readily available parts supply.

1986 Dodge Ramcharger

Just imagine a full-size, short wheel-base pickup with an enclosed bed. It looks an awful lot like our modern SUV. But back in 1986, they called it a Ramcharger. While Detroit saw a limited number of the trucks originally ordered, they remain popular with today’s collectors. They take well to customization and are always a rare find on any lot. Was the Ramcharger attractive? Well, beauty is in the eye of the beholder, so they say.

1990 Dodge Dakota Sport Convertible

Just when we thought pickup trucks were big enough for weekend adventures, the market started exploring the options of downsizing. The Dodge Dakota found popularity in the niche mid-size market. In 1990, Dodge decided to mix it up even more by issuing a special edition Dakota Sport Convertible. Only 3,700 were sold, which makes this a desirable and valuable collector car that is sure to score some trophies at your local show.

2000 Toyota Tundra

For years, the Japanese and Korean carmakers tried to elbow their way into the North American markets. Toyota finally managed to take a bite out of the pick-up truck segment with the debut of the 2000 Toyota Tundra. Now over twenty years old, if you have a pristine early Tundra in your garage, it is positioned to become an important representative of the changing light-duty pickup market in the twenty-first century at future classic car shows.

As you can see, the best classic pickup trucks can be a best-selling, special editions, or breakthrough models that helped to change the shape of automotive history. Which one belongs in your garage depends entirely on your desire to invest, restore, or customize a classic pickup truck.

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