Our area was settled in the main from two directions. As people traveled up the valley from Port Jervis to Kingston on the Old Mine Road now called Route 209, they began to cut roads up through the mountains to the west toward the Neversink River. From the same junction of the Neversink and Delaware Rivers in Port Jervis, many followed the Neversink River upstream toward the north.
There were shallow places which were easier to cross and by custom, these crossings were usually named for the families who settled at these points.
Thus the Hackeldam crossing was a mile or so below the present Bridgeville, at the end of Katrina Falls Road on the east side. Ties in the rock on the west side can still be seen which held up the swinging bridge there. It is known that lumber was hauled from Gilman’s Tannery and Settlement in Hartwood, Town of Forestburgh, across the Hackeldam, over the mountain to Westbrookville. The road was known as “Horse Thief Trail”. At one time, Elijah Silvieus owned property near Hackeldam and charged a penny to cross the swinging bridge.
Some of the original settlers in this area were named B.R. Griffen, R. Kirk, H. Case, and E.B. Silvieus. Wakeman’s Ford, a mile north (upriver) from Bridgeville, was settled about 1801-1802 by Jabez Wakeman who came from Connecticut. A cemetery is there from that period on the west side of the river. Then further upriver, the Dennistons settled and the crossing was named for them. To use that crossing now would lead into Thompsonville near the post office.
There was also a swinging bridge at Bridgeville prior to 1807 (it may have replaced the Hackeldam swinging bridge as the usual crossing). Then the famous wooden bridge was built in 1807. It was a span of one hundred and sixty feet and was the first covered bridge built in New York State and one of the very few designed with two lanes. This wooden bridge was one of the last key links in the Newburgh-Cochecton Turnpike which was chartered by businessmen from Sullivan and Orange Counties and begun about 1801, being completed in 1809 The bridge was engineered and built by Major Salmon Wheat, a farmer who lived near the present village of Howells. This bridge lasted one hundred and sixteen years and was torn down sometime after the iron bridge was opened in 1923. Only wooden fragments can still be seen on the downstream side of the river.
The Newburgh-Cochecton Turnpike was a toll road. One such toll house was located on old Route 17, east of Lord’s Pond (now Wanaksink) half-way to the Mamakating Town line, on the south side of the road. There was a post office there called Gales in 1838. The road was necessary to bring the products of the forests of Sullivan County to the markets in Newburgh and by boat, to the City of New York. Freight wagons carried charcoal, potash, tanbark, hand-split hemlock shingles butter firkins, barrel staves and hooks, grain scoops and shovels laboriously formed from hardwood by hand. Such were the industries of the area.
The iron bridge at Bridgeville opened in November, 1923 and is still in use on old Route 17, near the site of the present Holiday Mountain Ski Hill. This bridge cost S38,000 and the Town of Thompson sold bonds to finance it as there was no State aid at the time. In 1918, the iron bridge needed shoring up and the wooden supports were replaced by iron work made in Marathon, New York.
The most recent crossing of the Neversink at Bridgeville was constructed by New York State when the State-funded Route 17 was authorized. It shares the bulk of the traffic going north and west from New York City with the New York State Thruway which is quite some distance to the east.
Benjamin Lord Whipple noted during a recent interview that his Aunt Mallie Lord always remarked how she had lived on or during four roads without moving out of the house. First there was the dirt road, then cut planks were laid down and called the Newburgh-Cochecton Turnpike but the planks wore down unevenly. A map dated 1869 shows McAdamized road, and then it was called State Road # 17.
In 1913, the curve in the present road near Dodge Inn was called “Dead Man’s Curve” because it was so dangerous that lives were lost in accidents with the early autos.
Factory Road was so-named for the tannery which was near Gottlieb’s Pond in the hollow across the road from the dam of Wanaksink Lake (then called Fowlwood Lake).
In 1872, the New York & Oswego Midland RR was opened at Wurtsboro, and served as the detraining point for this area which was about six miles to the west.