One of the first settlers to the area was John Swinson, who received a large tract of land from the Earl of Granville, the last Lord proprietor in 1761.

Many of the early settlers were farmers whose principal crops of cotton and corn were sold in towns along the Tar and Roanoke Rivers.

Sheep, cattle, and hogs were also raised in large numbers and farmers often supplemented their income with shingle making, woodcrafts, and the production of tar and turpentine from the area's abundant forests.

The community's development was hindered by it not being located along a navigable stream or on either of the railroad lines traversing Martin County.

Records are limited, complicated by the fact that Bear Grass businesses were listed in directories with Williamston addresses because that was the nearest post office.

But by the turn of the century, the community consisted of several legal distilleries, cotton gins, sawmills, grist mills and blacksmith shops.

Reuben H. Rogerson's two story steam-powered sawmill and cotton gin was one of the area's largest before being destroyed by fire in November 1908.

[citation needed] Local artist Henry C. Cowen created two statues that enliven the Bear Grass School campus.