Benjamin Cutbirth, Sr was born about 1740 in either Augusta Co., VA or Pennsylvania. In 1761, he married Elizabeth Boone Wilcocksen, a niece of Daniel Boone, in the Yadkin Forks region of North Carolina, where he had located a year earlier. Daniel Boone Cutbirth, the first of their four children, was born in 1763. Ben, Jr was born about 1765, Mary in 1771 and Sarah in 1772. All the children were born in the Watauga area of North Carolina.

Cutbirth was reputed to be a longhunter with Daniel Boone, the two saving each other's lives several times. In Clark's Kentucky: A Land of Contrast, "Longhunting was not an unknown pastime for Daniel Boone. He had hunted with such seasoned woodsmen as Benjamin Cutbirth for game and land along the Watauga in Eastern Tennessee." Believed to be the one who introduced Daniel Boone to the Kentucky wilderness, only Cutbirth's illiteracy kept him from becoming as famous as Boone himself. Cutbirth and three others are considered to be the first white men to reach the Mississippi River overland in about 1767, viewing the river from the Missouri Boot Heel area. They took the pelts they had collected south to sell them in New Orleans and returned through the Indian Territory of present-day Mississippi and Alabama, only to be robbed of their earnings by a band of Indians.

Cutbirth is shown as a resident of Tennessee in 1794, in Johnson County. In 1799, he sold his lands in East Tennessee and left for Middle Tennessee, where in 1807 he was one of the signers on a petition to form Maury County. He lived briefly in the Shoal Creek area of Alabama in the Cherokee Nation and then moved back to Maury County, where he shows up on a tax list for 1811 with his son, Daniel. (The August 25, 1814 issue of The Columbia Chronicle includes his name among petitioners who were forced off the Cherokee land.) Cutbirth died about 1817 and is buried in Major Howell Cemetery in Giles County. His wife Elizabeth died in 1819 and is buried beside him.

Listed by the DAR as a Revolutionary patriot, Cutbirth was once held hostage in his own home by a band of Tories. His exploits have been honored by a marker in Kentucky, which commemorates the service of all those who helped cut the Wilderness Road. The marker reads (in part): "In testimony of the gratitude of posterity for the historic service of cutting the Transylvania Trail �the first great pathway to the West, March - April 1755, from Long Island of � Holston River, Tennessee, to � Otter Creek in Kentucky, by a gallant band of axemen, pioneers and Indian fighters, who � opened the doors of destiny to � Kentucky and the West."