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The first Clevelands were built by the American Cycle Manufacturing Company of Hartford, Conneticut. They shared with the American, and several other marque labels, configuration nearly identical to the first Indian motorcycles. Which actually came first remains a matter of dispute.
The more recognizable and distinct Clevelands were made by the Cleveland Motorcycle Manufacturing Company in Ohio. The 220cc two-stroke engine was mounted transverse to the frame, with a worm drive to power the countershaft sprocket for final chain drive. The shaft exited the two-speed gearbox and extended past the rear downtube to drive the magneto, hung just forward of the rear wheel.
In 1920 the machine grew larger, adding footboards, incorporated fuel/oil tank and wider fenders. The weight went up again the following year with a larger fuel/oil tank and seat and a battery. To offset the additonal load, the engine displacement was enlarged to 270cc. For 1923 the company offered a sport solo Model E, with battery and electric lights.
Although the Cleveland two-stokes appeared a little flimsy compared to some motorcycles of the period, their light weight and moderate power combined for easy riding. When heavy weather and nasty terrain slowed heavier machines, the Cleveland was more apt to plug on regardless. The two-strokes set several lightweigh endurance records and routinely won their division in 100- and 200-mile races.
So their was a market for a $150, 150-pound motorcycle of moderate power and few pretensions. The Cleveland Light served a wide market of working stiffs who couldn't afford a Flying Merkel ($275), and women riders who appreciated the light weight and handling ease. Indian also offered a two-stroke single at the same price, but their K model was a heavier and taller machine.
The two-stroke was in production until 1925, when it was superseded by a 350cc four-stroke single designated the F-25. Also a two-speed, the F model was heavier, slower and destined for a brief production run. Then in a lavish burst of Lake Erie optimism, Cleveland hired automobile engineer L.E. Fowler and built a four-cylinder motorcycle.
The 600cc T-head four was a single-valve, with the intake cam on the left and exhaust cam on the right. Cleveland retained the perimeter cradle frame design with the four-cyclinder engine hung in the middle. Additional tubing connected the frame's mid-section to the rear axle, and a leading link spring fork graced the front end. The engine, patterned on the Pierce four, had a three-speed transmission. But the 600cc four was well off the performance pace set by Henderson and Ace, and the next engine was a 750cc F-head four designed by former Henderson engineer Everett DeLong. The engine was a four-pot monobloc casting, with the cylinder head and intake manifold in a single casting. The three-speed transmission could be removed without removing the engine. The new chassis featured a traditional split-downtube cradle frame and no rear suspension.
In 1927 the displacement went to 1000cc, and the Cleveland was no longer sucking wind behind the Henderson and Ace fours. The engine was rubber-mounted and the motorcycle was the first on the market with a front drum brake. The four's finale came with the Tornado in 1929. A new frame dropped the seat by 2.5 inches, and light alloy pistons and more compression increasing power. For 1930 Cleveland announced the Century model guaranteed good for at least 100mph, with a brass plaque to certify it had been pretested at that speed.
But as the Century entered production, the Wall Street stock market collapsed and the Cleveland Motorcycle Manufacturing Commpany soon followed suit.