It probably all started with simple log rollers.
The oldest known archeological evidence of the wheel dates from around 3500 B.C., and was found in Mesopotamia. The wheel and axle is a simple machine which is more efficient because the larger diameter wheel covers a longer ground distance for each turn of the axle than a single diameter log roller. The invention of the wheel was likely based on the observation that log rollers with worn down centers were easier to use than new ones.
Add the domesticated horse to the wheel, and you not only have the technology for a war chariot, but also the horse and wagon, a technology so suitable to the needs of men that it would remain the peak of land transportation technology for millennia. At some point early men also developed large dugout canoes which could move heavy loads over long distances on water, and small hide or reed boats which were good for fishing or crossing narrow bodies of water. After the horse and cart, most of the advances, until the steam engine would provide a new kind of horsepower, would be in water transport.
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