On December 17, 1853, by an act of the Sullivan County Supervisors, the towns of Highand and Tusten were taken from the Town of Lumberland and each made an independent town.  Both towns are in the southwestern part of the county along the Delaware River.

The Town of Highland was named after the geography of its land.  the "highlands" between the Delaware River and the Mongaup river rises to 1,300 feet in some places in this town.  the town is sparsely populated and made up of woodland, streams and small lakes.

Highland was not settled until after the Revolutionary War, although one of the bloodiest battles of that war was fought on the headland above Minisink Ford in the town.  It was here that the notorious Tory, Joseph Brant, led a bloody massacre on two companies of colonials from the Goshen area.  today a monument stands on the wooded hill above the Delaware as s tribute to those brave soldiers who lost their lives.  Interestingly, it was not until 43 years after the battle that the remains of those slain were recovered from the battlefield and laid to rest in Orange County.

John Barnes was the Town of Highland's first inhabitant, settling at Narrow Falls, which is about one mile above the mouth of the Lackawaxen River.  Nathaniel Wheeler was hired as the first teacher, schooling in the Beaver Brook area.  Phineas Terry started the first store in 1828 and G. Ferguson opened the first tavern in 1830.

The Town of Highland was a slow growing area.  The primary industry during its early development was lumbering.  The part of Highland along the Delaware River was one of the more active sites where timber was cut and tied into rafts and floated down the river to Philadelphia where the logs were used as spaars in the shipbuilding industry.  There were numerous sawmills in the town during its lumbering heyday.  Because much of the area was heavily forested with rocky soil, most of the township made poor farmland.  Early farming families were discouraged from settling here limiting early growth of the region.  It was not until the Delaware and Hudson canal was opened in 1828 that the region was opened to the outside world.  When the Erie Railroad was completed the area began to enjoy a tourist business.  The boarding houses and small summer hotels built in the Town of Highland catered mostly to German and Irish guests.

Today much of Highland is still undeveloped.  The main industry in the town is tourism generated by the Delaware River.  The rustic beauty of the area and recreations enjoyed on the river attract visitors from near and far.

There are a number of small hamlets in the Town of Highland.  One of these is Barryville, which was named after the U.S. Postmaster, William T. Barry, who was in office in 1832 when the post office there was established.  Barryville owes its existence to the D & H Canal, which ran along the southern border of Highland.  In 1856, a bridge was completed at Barryville, connecting it to Shohola, PA.  This provided Barryville easy access to the New York and Erie Railroad depot that was located in Shohola.

A short distance from Barryville, at Minisink Ford, is the historic Roebling Bridge.  This bridge originally served as an aqueduct for the canal to carry boats across the Delaware River.  Before the bridge was built, there were numerous collisions between the canal boats loaded with Pennsylvanian coal crossing the river and rafts of logs making their way downstream.  The bridge was built in 1848 and designed by John A. Roebling, who later designed the Brooklyn Bridge.  It is America's oldest wire rope suspension bridge and is listed by the Historic American Engineering Record and is a national historic landmark.  Roebling's bridge served the canal un1898.  The bridge has been renovated for highway travel between Minisink Ford and Lackawaxen.

The hamlet of Eldred was first known as Half-way Brook.  Half-way Brook (the stream) was so named because when traveling by an ancient trail, this stream was located half way between the Mongaup and the Delaware Rivers.  In 1875, the postmaster C .P. Eldred renamed the post office in memory of his father, James Eldred.

The inhabitants of Yulan originally wanted to name their hamlet "Laurel" or "Mountain Laurel".  However, the postal department determined that there were already too many places with the same name.  Not to be discouraged, the people came up with the name Yulan, which is the Japanese word for laurel.