The Delaware River acts to draw together the communities throughout the Upper Delaware River Valley. Settlements on both the New York and the Pennsylvania sides of the river popped up in this place owing to the natural beauty of the river itself, and the scenic and recreational benefits it provides.

However, as much as the river may be the tie that binds, in a grand, spiritual sense, it’s also, logistically, a great big body of water that splits the region in two, separating the state of New York from the state of Pennsylvania. The history of settlement in this region is filled with the stories of the people who have set out to cross that divide, first with ferries, then with toll bridges, and then, ultimately, with the set of toll-free bridges that span the river today.

To toll or not to toll

Originally, the way people got across the river was through the use of ferries. Over time, as the volume of traffic increased and the need for more permanent crossings grew apparent, communities came together to construct bridges in their stead.

These early bridges were operated by and large as toll bridges. One such bridge connected the settlements of Narrowsburg, NY and Darbytown, PA. When the crossing first operated in the early 1800s, tolls were 37 cents for a one-horse waggon, $1 for four horses and six cents for a person walking. While the original bridges at this crossing were made of wood, it received an iron bridge in 1899; the current bridge in this location dates back to 1954.

Another of the early toll bridges came from the Cochecton Bridge Company, which incorporated in 1817 to build a bridge connecting Cochecton, NY and Damascus, PA. The original bridge was completed in 1819; when that collapsed, it was rebuilt in 1821, and lasted until 1846.

Eventually, residents of the river valley got a break from the tolls. The New York-Pennsylvania Joint Interstate Bridge Commission formed in 1919 to manage the bridges connecting the two states along the Upper Delaware River. As the commission bought and reconstructed the bridges along the Upper Delaware, the tolls on those bridges fell away, leading to the smooth and toll-less traveling experience of today.

Currently, the commission manages nine bridges (it would be 10, but for the dearly departed Skinners Falls Bridge); the National Park Service manages the Roebling Bridge separately from the scope of the commission’s work.

The last of the bridges bought by the commission, Kellam’s Bridge, remained a toll bridge up until 1932. That bridge had been constructed in 1889 to connect Manchester, PA and Fremont, NY; while the commission kept the bridge with much the same design up until the present day, a major renovation in 1936 replaced much of the original material.

Skinners Falls Bridge

The Skinners Falls, a feature on the Delaware River, are named after Daniel Skinner, the famed “Lord High Admiral” of the Delaware who kicked off the region’s timber rafting trade in 1764. Fast forward nearly a hundred and fifty years to the start of the 1900s, and Milton Skinner, Daniel’s great-grandson, was running a ferry crossing at that point in the river.

As ferry traffic increased, spurred by the presence of the Erie Railroad on the New York side of the river, Milton sought to construct a permanent crossing at that location. The Milanville Bridge Company, with Milton Skinner at the head, was chartered in 1901 for that purpose. The company hired Ambridge, a subsidiary of Andrew Carnegie’s U.S. Steel Corp., originally created by J. P. Morgan, to construct it.

The bridge, completed in 1902, was a rare example of a Baltimore Truss bridge. It cost $14,000 in 1901 dollars, which comes to $472,255.35 in 2026 dollars, according to the U.S. Inflation Calculator. It was only a one-lane bridge; historians suggest that may be as the result of a compromise with the bridges in Narrowsburg (downstream) and Cochecton (upstream), which stood to see drops in toll revenue thanks to this new competitor.

The Skinners Falls Bridge suffered damage in 1904, when an ice sheet took the New York span of the bridge downstream; but after it was repaired, it lasted until 2025. After years of on-and-off shutdowns and makeshift repairs, the Pennsylvania Department of Transportation made the decision to take it down, saying that it had deteriorated beyond the possibility of repair.

Roebling Bridge

Currently, the Roebling Bridge operates as a one-lane road, taking cars over the Delaware River between Lackawaxen, PA and Highland, NY. However, it was constructed as the Roebling Aqueduct, conveying canal boats over the Delaware River on their journey through the D&H Canal.

The D&H Canal brought coal from Northeast Pennsylvania to the Hudson River, where it went ultimately to power furnaces in New York City. In the mid 1800s, the D&H Canal Company sought to resolve a bottleneck with its boats crossing the Delaware River by constructing an aqueduct to carry them above it.

Architect John Roebling suggested the use of a new technology—wire rope suspension—for the construction of the bridge. That technology allowed the bridge to cross the Delaware River using only three piers, and allowed it to sit higher in the air, with more clearance between itself and the river. The bridge was largely finished by the winter of 1848 and opened for business in 1849.

Roebling went on to a long and illustrious career, with his crowning achievement—the Brooklyn Bridge—built to his design by his son following his death, using the same suspension principles as were used for the aqueduct. Meanwhile, the aqueduct continued to serve the D&H Canal until the canal’s closure in the late 1800s.

Since then, the Roebling Aqueduct has found a second life as a bridge, an afterlife that’s lasted over twice as long as the original life. In 1901, the structure was bought and converted for vehicular travel; it served that purpose for a time in private hands, though it deteriorated to the point that, in 1977, a truck fell through the deck. In 1980, the National Park Service stepped in and bought the structure, renovating it and rehabilitating it while keeping much of its original metalwork intact.