A frontier trail in North America opened by Daniel Boone in 1775 across the Allegheny Mountains. It ran for nearly 482 km (300 miles) from western Virginia through the Cumberland Gap to the upper Kentucky River at Boonesborough. It was commissioned by the Transylvania Company, an association of land speculators, to encourage settlement in Kentucky, Tennessee, and the Ohio valley. For 50 years it was a major route into the eastern Mississippi valley.