Early Roads  In Obion Co, TN The first roads in northwest Tennessee were Indian Trails running generally from the east to the Mississippi bluffs. An early Mississippi river bluff stop, Mill's Point, is now known as Hickman KY.   Early settlers followed these narrow trails into the territory and cut trees and undergrowth to allow the first wagons to pass.  Rivers, sloughs, and creeks overflowed the bottom lands and while Native American Indians hunted the territory, few were permanent dwellers.

After white men came, the county court was quick to set up a tax plan and appoint men to lay out roads, many following Indian trails.   It isn't known, but suspected that the men appointed were also grant holders of land the road crossed or were members of that settlement.

Very soon, roads were widened to accommodate two or four horse stage coach carrying mail and passengers. Prior to 1830, one known mail route came from through the northeast corner of the county from Dresden to Totten's Wells near Harris Station, and on to Troy.   By 1840, Totten's Wells in Obion County was the mid point of the road between Dresden and Mills Point (Hickman, KY).  From Dresden the road went northeast to Paris and crossed the Tennessee River at Reynoldsburg and on to Nashville.

Another road ran from Jackson, through Trenton and Yorkville, entered Obion County at Mason Hall.  In Gibson County it was called Base Line Road and in Obion County the first section was called the Turnpike Road and followed an old Indian trail.   Crossing the Obion River, the road passed through Troy and continued west and north toward Hickman.  The section beyond Troy going north was later called the Troy-Hickman Road and much of it is still used today.

"Turnpikes" were dirt-filled roads financed by tolls and named for the gates across the road and the sharp pole or pike on the gate allowing it to open or close. These were chartered by the state legislature, but privately owned. In 1870 the General Assembly repealed a charter for a turnpike across the North Fork of the Obion and released the owners from the obligation of keeping the road passable or collecting tolls.

In 1841, a second bridge was built across the Obion River by the Obion and Gibson county Turnpike Company.  this bridge stood until about 1900 and was replaced with a steel bridge.  In 1978 some of the old concrete pilings were still standing.

From Dyersburg a road crossed the Obion River at Sharp's ferry, passed through Glass and Mt. Moriah and onto Troy. Later a connection was made between Troy and Totten's Wells and to Dresden. At one time a road ran from Troy to the Obion River south of Rives and on to Dresden.