Cultural Resources include: r landing and early bridge site along Tuckahoe River, colonial brick public tobacco warehouse, tannery, shoe factory, cannery sites, tavern, and Maryland, Delaware and Virginia Railroad Company connecting station.
Hillsboro is located in Caroline County on the Tuckahoe River at the point where Queen Anne and Talbot Counties meet the river on the opposite side. Prior to 1750 a bridge had been built across the Tuckahoe River, thus the original name Tuckahoe Bridge. The name was later changed to Hillsborough and eventually shortened to Hillsboro.
Francis Sellers built a brick house and brick warehouse near the eastern terminus of the bridge before 1742. Hawkins Downs was appointed tobacco inspector at Tuckahoe Bridge on October 4, 1748. A "rowling house" was located on the east side of Tuckahoe River about 300 yards south of the original bridge, possibly where iron was rolled and hammered into shape. A tavern was located here before 1787. Charles Wilson Peale, one of America's great painters, and his son Rembrandt Peale once resided at or near Hillsboro. A tannery was also located at Hillsboro.
Caleb Clark Wheeler moved his general store from Gilpin Point to Hillsboro about 1870. He began to ship grain to Baltimore and his business eventually grew into the Wheeler Transportation Line. His headquarters were located in a small office in a granary at Hillsboro Wharf furnished with an iron safe and two small desks. A Captain Kemp acted as office manager, general handyman and wharfmaster. Larger vessels could not ascend the Tuckahoe River as far as Hillsboro and used Wayman's Wharf, a few miles to the south (see Waymans Landing). Kemp also drove a carriage between Hillsboro and Wayman's Wharf. A footpath known as "Sailor's Path" also led between these two points, named for the steamboat deckhands, many of who had homes in Hillsboro. At least one vessel, a sloop, was built at Hillsboro in 1870.
Several granaries were clustered on both sides of the bridge along the river. Scows were loaded with 3,000 bushels of bagged grain through chutes and then poled down on the ebb tide to Waymans Wharf. One man steered while two more worked a push pole while walking down each side. The following canneries operated at Hillsboro:
- H. S. Fisher (1897)
- Stewart & Jarrell (1910-1919)
- Charles Jarrell (1920-1955)
- Hillsboro-Queen Anne Coop., Inc. (1932-1944)
- Southern States Hillsboro-Queen Anne Coop. (1945-1953)