By 1702 a bridge had been built across the Tuckahoe River, thus the original name Tuckahoe Bridge. The name of the area was later changed to Hillsboro (see Hillsboro). The first bridge across this area was built at a ford or "wading place" along the road between Ridgely and Greensboro, then called "St. Joans Path."
The first mention of the Tuckahoe bridge was in an Act of the Maryland Assembly dated 1706. In 1775 the court agreed to "make Tuckahoe Bridge passable." An Act dated 1781 stated the bridge was nearly impassable and authorized construction of new bridge at the same site. A later Act dated November 1794 states, "...that the bridge over Tuckahoe creek [located opposite a place formerly known as "the Old Rolling House"] is in ruinous and almost impassable condition..." The act states the original bridge was authorized after petition by Queen Anne, Talbot and Caroline Counties to the Maryland General Assembly and that the same three counties paid and maintained same. But this 1794 Act called for the counties to be levied 150 pounds and to built the new bridge "about 300 yards below the place of the old bridge" which would shorten the distance for travelers. This bridge was built 300 yards south of the old bridge. Both bridges were apparently used for an unknown period of time after the new bridge was built. A scow was reputedly visible at low water just above the bridge in the late 1980s.