10 Classic Harley

These classic Harley-Davidson motorcycles are some of the most important ones in the brand's history, and their price tags today reflect exactly that.

In the motorcycling world, there aren't a lot of names bigger than that of Harley-Davidson. Over the course of 120 historic years, Harley-Davidson Motorcycles has built some of the most powerful, iconic, and legendary motorcycles the world has ever seen. As such, the brand has rightfully earned its place in the two-wheeler hall of fame. In fact, Harley-Davidson is one of the strongest pillars of this hall of fame itself. Harley wouldn't have been the name it is today without some of the greatest, best-selling, and most impressive motorcycles over the course of their history, and these Harley motorcycles from the past are still just as important, not just to the American manufacturer, but motoring enthusiasts across the world.

Over Harley-Davidson's history, motorcycles like the Twin, engines like the 'Panhead' and the 'Knucklehead', have always been coveted, so much so that they command a fortune at auction. These old motorcycles are classic icons today, and are well worth the arm and leg they cost today. Everybody wants to own a Harley, and while some Harley motorcycles are quite cheap today, there are those iconic models which cost an arm and a leg. With that said, here are 10 classic Harley-Davidson motorcycles that are worth quite a fortune today.

We've compiled historic and pricing data from official sources like Mecum Auctions in order to best provide an account of some of the most expensive classic Harley-Davidson motorcycles today.

Harley-Davidson only built 158 E-Model units, owing to the war effort. Armed with the legendary Knucklehead engine displacing 61 cubic-inches, this 1943 Harley-Davidson E-Model ran on a four-speed transmission. In fact, the war effort channeled most of Harley's resources, leaving civilian motorcycles to cut corners.

As such, even this '43 E-Model from Harley didn't have stainless steel, with its front fender lamps absent, and even the seat itself had to be made of horsehair inside. For the 1943 model year, Harley built 158 Model-E units, which makes it one of the rarest Model-E Harley-Davidson motorcycles. Mecum auctions displays this 1943 Model-E as sold for $220,000 at the 2021 Las Vegas Vintage and Antique Motorcycle Auction.

In 2014, this 1912 Harley-Davidson 8A Twin surprised auctioneers when it went up from its expected auction price of $100,000+ to a whopping $236,500. One of the first-ever twin-cylinder motorcycles with a belt driver and Idler wheel. Armed with a 61 cubic-inch air-cooled V-twin engine, this 1912 8A Twin made all of 8 horsepower.

Sure, that isn't a lot today, but it was pretty damn impressive over a century ago. Understandably, not a lot of models of this classic Harley-Davidson motorcycle are left today, which is why it cost an eye-watering amount of $236,000 when it was sold almost a decade ago.

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Now, the Harley-Davidson 7D Twin, back in 1911, was more of a promotional motorcycle rather than a proper commercial machine for Harley-Davidson. Equipped with a 811cc V-twin engine, the 1911 7D Twin laid the foundations of the iconic V-twin tradition that Harley motorcycles, to this day, continue to follow.

Only four models of this 1911 Harley motorcycle are known to have existed, one of which was sold in 2014 for a whopping $284,000. If you're trying to compare, well, this 6-7 hp motorcycle cost almost six times the price of the most expensive Harley-Davidson motorcycle on the market today.

Displayed and auctioned at the 2021 Las Vegas Vintage and Antique Motorcycle Auction, this 1907 Harley-Davidson Strap Tank cost its new owner a whopping $297,000. In fact, even after being set back by nearly $300,000, this classic Harley is for display purposes only, and its Nevada owner can't actually ride it on the highway or public roads.

What's most impressive about this 116-year-old motorcycle, however, is that it retains its original factory engine, down to the original gas tank, the carburetor, and even the belt tensioner. If that wasn't enough, the 1907 Harley Strap Tank, sold in 2021 for $297k, even retains its original wheel hubs, front forks, and the very seat, too. It stands as a testament to the early motorcycles that made Harley-Davidson the world-famous motorcycle brand it is today.

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A true classic produced by Harley-Davidson back in the '50s, the FHL is world-renowned for its great power (for its time), all thanks to the 74-cubic-inch motor it ran on. Its stylish yet functional fairing aside, there was something far bigger that made this 1959 Harley FHL significant enough to net over $350,000 on the auction block. Its looks also make it one of the best-looking and most badass Harleys ever, too.

This Harley-Davidson FHL was a gift to 'The Killer', Jerry Lee Lewis himself. Presented as a gift, this classic Harley motorcycle actually managed to spark a friendly rivalry between Lewis and Elvis Presley himself, since the latter claimed it was actually him that Harley was supposed to gift the motorcycle to. It is this history that makes the '59 FHL worthy of its $358k price tag.

One glimpse at the 1909 Harley-Davidson Model 5D Twin, and you'd fall in love. We wouldn't blame you, either. A pretty remarkable machine built for performance, the Model 5D Twin was Harley-Davidson's first-ever twin-engine bike. Harley only ever built 27 models of the 5D Twin, and one such model stands beautifully in a museum in Milwaukee.

Valued at a whopping $550,000, this classic Harley-Davidson motorcycle from 1909 is, of course, quite worthy of its half-million price tag. Interestingly enough, the rear wheel of this Model 5D twin was powered by a leather belt of all things!

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The Strap Tank is decidedly one of Harley's most famous early motorcycles. Harley-Davidson only ever made 150 of these classic motorcycles, and each one seems to be more valuable than the last. Built in 1907, the Strap Tank was armed with a 42 cubic-inch engine making 7 horsepower. In fact, it is the Strap Tank's exterior that makes it look so p[leasing to the eye, with curved handlebars and a leather saddle.

This particular classic Harley-Davidson motorcycle spent eight decades in the possession of a family, before collector E.J. Cole took it off their hands, and displayed it at the National Motorcycle Museum and Hall of Fame in Sturgis, South Dakota. This classic American motorcycle sold for an eye-watering $715,000, and looking at its history and significance to the Harley brand, it's well worth its three-quarter-million evaluation.

One of the latest and most expensive Harley-Davidsons ever sold, this 1908 Strap Tank sold for nearly a million dollars. This classic Harley was a 1941 barn find, where it was restored expertly in Indiana. With its original tank, wheels, engine belt pulley, seat cover, and muffler sleeve intact, this 1908 Harley-Davidson motorcycle is just one of a dozen.

In fact, even fewer than a dozen are considered to be in a correct condition. There's a reason the Strap Tank is as sought-after as it is, and so popular on the auction block - all the prototypes from Harley that preceded it are long gone today, which means that this classic Harley is truly the earliest of Harleys you could find. A truly exceptional machine in all ways, this 1908 Harley-Davidson Strap Tank sold for a staggering $935,000 at the 2023 Las Vegas Vintage and Antique Motorcycle Auction.

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This classic Harley-Davidson is renowned for its high-performance. Powerful, fast, and agile, the Harley 8-Valve Racer is actually a pretty enjoyable 107-year-old track toy. The 998cc engine was a twin, of course, and boasted 8 valves, which helped the motor take the bike to high speeds, and get there quicker, too.

The lightweight chassis of this million-dollar Harley helped the motorcycle remain agile and stable at higher speeds as well. The 8-Valve Racer from Harley had its merits proven all the way back in 1916, when it helped Irving Janke win America's most prestigious race, the Dodge City 300. As such, this Harley-Davidson racer has been one of the most expensive Harley-Davidson motorcycles ever, known to go for $1 million, and rightly so.

2014 was most certainly a big year for Harley-Davidson auctions, wasn't it? Adding to the list of mind-bogglingly expensive classic Harley motorcycles sold in 2014, is the 1969 Harley-Davidson 'Easy Rider' Captain America motorcycle. If you're wondering why this motorcycle looks faintly familiar, you might have caught it in the popular 1969 road movie 'Easy Rider', being ridden by Peter Fonda himself.

Not only is this classic motorcycle one of the most iconic Harley motorcycles, but it's also significant because of its showbiz roots. In fact, the significance doesn't end there, as this Easy Rider Harley-Davidson is believed to have paired a '52 H-D Hydroglide with '62 Pinheads. One thing is certain, though - they don't come any more special than this. As such, this classic Harley rightly fetched a $1.35 million price in 2014.

If it has wheels and an engine, Samarveer Singh is going to be obsessed with it. He is a budding Indian motorcycle racer, competing at the national level in his country in his very first year, chasing his dream around every corner of the racetrack. A touring enthusiast, Samarveer is forever stuck between the urge to constantly redline his bike, or save its clutch plates for longer.