The Town of Highland was named for its hilly elevated terrain, lying north of the Delaware River. The river forms the southwest border of the town and Sullivan County. The town’s population was 2,530 at the 2010 census. The town was formed from the subdivision of the Town of Lumberland in 1853, which also created the westerly neighboring Town of Tusten. According to the US Census Bureau, the town has a total area of 51.7 square miles, of which, 50.0 square miles is land and 1.7 square miles is water surface.

On that southern border, Barryville is named for William T. Barry, postmaster general under President Andrew Jackson. The community grew up around the Delaware & Hudson Canal, which opened in 1828 and operated until 1898. The canal ran through what is today the center of the hamlet, and the canal company operated a number of stores, an office and a drydock there.

The Upper Delaware River, today a unit of the National Park system, then also served as the conduit for timber cut in the area and rafted to Philadelphia for use in the ship building industry. In 1899, John Willard Johnston, lawyer, historian, and the town of Highland’s first supervisor, wrote a first-hand, biting local history of the canal period, which was published as “Remiscences.”

Eldred, named for the hamlet’s first settler Charles Eldred, is at the town’s center and is the seat of town government. Two other hamlets include Highland Lake at the northeast and Yulan (Chinese for laurel) to the west.  Early settlers here earned their living by farming and from harvesting the abundant timber.  Late in the 19th Century, the nearby Erie Railroad brought vacation visitors and the creation of the boardinghouse industry, which has since evolved into recreation, camping, and second homes.

The Highland neighborhood of Minisink Ford is the home of the Delaware River Aqueduct for the former Delaware and Hudson Canal, a National Engineering Landmark, which was built in 1848 by Brooklyn Bridge builder John Roebling and is recognized as the world's oldest surviving wire rope cable suspension bridge.

Nearby at Minisink Ford, Sullivan County manages the Minisink Battleground Park, site of the 1779 engagement between raiding British Tories & Mohawk Indians pursued by  militia from Orange County, NY and Sussex County, NJ.