Toll Road: Paying for the Turnpike to Sag Harbor

The tollhouse on the Bridgehampton-Sag Harbor Turnpike at the turn of the 20th century
The tollhouse on the Bridgehampton-Sag Harbor Turnpike at the turn of the 20th century, Photo: Courtesy Bridgehampton Museum

I was looking through some back issues of Dan’s Papers the other day and came upon an article written in 1997 about the passage of what was then the new Comprehensive Plan for the Town of Southampton.

This plan had cost the town several hundred thousand dollars to produce. It ran to hundreds of pages. And far down deep into it, there was this idea presented to put up a tollbooth on the Shinnecock Canal. It’s on pages 430-431.

“…a vehicle toll collection system (at the Shinnecock Canal Bridge) would reduce traffic by 10% to 20% with 25% of this reduced traffic diverted to rail service…the cost of the toll changing by time of day, or day of week, or season, with higher tolls paid during peak periods of congestion and lower tolls during off-peak periods….The toll facility could be designed in keeping with Southampton’s resort and rural image perhaps featuring shingle facing, and a Shinnecock Canal visitor’s center.”

It’s often mentioned by frustrated local and summer citizens that we ought to put a gate at the Shinnecock Canal, but this is the only time I ever recall it actually put down in a comprehensive town plan as a possibility. It was, of course, never carried out.

There was, however, way back in our history, a toll to take a trip on a highway to the most important destination on the East End at the time. It was a dirt road that went from Bridgehampton to Sag Harbor, and it thrived for two generations beginning in 1840.

The Village of Sag Harbor had already become, by that time, a very important commercial hub. It had developed as one of the four premier whaling ports in the country—along with New Bedford, Nantucket and Lahaina, Hawaii. It had become so important, the federal government established a port of entry there. Earlier, in 1813, the British, out to teach America a lesson for declaring war on them in 1812, bombarded Sag Harbor from several men-o-war offshore and, briefly held Long Wharf before being driven off by American cannon fire from a nearby hilltop.

By the 1820s, Sag Harbor was alive with crewmen, slaves, harpooners and people from far-off lands speaking more than a dozen foreign languages. There were slaves in Sag Harbor and on Shelter Island. It wasn’t until 1827 that slavery was declared illegal in New York State. In 1847, 60 whaling ships went around the world in search of whales from their home base at Long Wharf. Herman Melville mentions Sag Harbor in four chapters of Moby Dick. James Fenimore Cooper wrote his first novel, Precaution, while at Duke Fordham’s Inn, and the Natty Bumppo character from the Leatherstocking Tales was based on a Sag Harbor whaling captain.

It was, during all this time, difficult to get through the woods between Sag Harbor to the old towns along the ocean, East Hampton, Bridgehampton and Southampton, where the main road to New York City ran through. Paths had been hacked away for carts and carriages for the six miles to Bridgehampton or East Hampton. But overgrowth often slowed passage, and there were washouts and other problems along the way.

In 1833, three men from this area approached the State Legislature in Albany, asking permission to build a toll road between Bridgehampton and Sag Harbor. There would be a tollhouse, a fence across it with a gate, and then the dirt road, fairly straight and well kept to allow a clear, wide passage between the section of Bridgehampton known as Bull’s Head—where the war memorial is today—and the outskirts of the already built-up Village of Sag Harbor at the Otter Pond Bridge.

The men were Samuel L’Hommedieu Jr. and William R. Sleight of Sag Harbor and Abraham T. Rose of Bridgehampton. And on April 29, 1833 the state granted them the right to form the Bull’s Head Turnpike Company, a corporation endowed with $4,000, that could sell shares to the general public at $20 each.

“The said corporation shall make a good and sufficient turnpike road from Bull’s Head, to Sagg-Harbor aforesaid, commencing between the store of James M. Niles and the inn of Richard Gelston …” the grant states.

The state also, defending its taxpayers, spelled out exactly what could be charged for the six-mile run between the two towns. It’s in the minutes of the activities of that day at the legislature, just before a passage authorizing the repair of roofs on the public buildings in Albany at a cost of $20,000 and a new law prohibiting any private citizen in the state buying or selling a business using a fictitious name.

The publication of these rates gives a remarkable window into what traffic was like back then.

19th century map featuring two toll sites
19th century map featuring two toll gates, Photo: From the Collections of the Suffolk County Historical Society

“For every wagon or cart drawn by two horses, mules or oxen, 8 cents. And for every additional horse, mule or ox, 2 cents. For every wagon or cart drawn by one horse or mule, 4 cents. For every coach, coachee, barouche, phaeton or other four-wheeled pleasure carriage drawn by two horses 16 cents. And for every additional horse, 3 cents. For every stage, wagon or coach, for the transportation of passengers drawn by two horses 12 cents. And for every additional horse, 3 cents. For every chair, or other two wheeled pleasure carriage or small wagon or other four wheeled pleasure carriage drawn by one horse 6 cents. And for every additional horse, 3 cents. For every horse and rider, 3 cents. And for every horse—led or drove—without being attached to a carriage 1 cent. For every sled, or sleigh, drawn by one horse, mule or ox 4 cents. And for every additional horse, mule or ox 2 cents. For every score of cattle or mules 10 cents. For every score of hogs or sheep 4 cents. And in the same proportion for a greater or less number of cattle, mules, hogs or sheep.”

Imagine reading that at the tollbooth to the Midtown Tunnel heading into Manhattan. And of course, there was no E-Z Pass.

It took quite a while to put this toll road to Sag Harbor together. The company was open for business and began collecting tolls in 1837. The tollbooth itself was actually a house built on the west side of the road. It is believed the toll collector’s family lived there.

One of the three founders of this corporation, Abraham Topping Rose, was a prominent attorney who had earned a law degree from Yale. He married the daughter of a former mayor of the City of New York and moved with her to Bridgehampton, where together they raised a family of six children. For many years, they lived in the Nathaniel Rogers mansion on the south side of the Montauk Highway at Bull’s Head, but around 1842 Rose built their own mansion across the street and facing the Nathaniel Rogers House. The mansion became known as the Abraham Rose House. Rose became a county judge in 1847. He died in 1857 at the age of 65.

The Bull’s Head & Sag Harbor Turnpike was a very successful venture. Four years after it opened, a second toll road was opened between East Hampton and Sag Harbor, in 1844, with similar prices. Things took a bit of a turn for the worse, however, when the Long Island Railroad opened a spur to Bridgehampton and then on to Sag Harbor in 1870. Many people now transported things by the railroad spur. The company stopped collecting tolls in 1901, and the town took control of the road and its abandoned tollhouse in 1906, shortly after the tollhouse for the East Hampton road was abandoned. The Bull’s Head toll house burned to the ground in 1909.

As you know, today, there is no railroad anymore between Bridgehampton and Sag Harbor. The railroad just continues on out from Bridgehampton to East Hampton and Montauk.

After the whaling industry came to a close, the commerce into and out of that town went into decline. In 1940, rail service between Bridgehampton and Sag Harbor ended, and the steel tracks were torn up for use in World War II.

Today, Abraham Topping Rose’s house has been reborn and restored for about $17 million and has become the Topping Rose House. Across the street, the Nathaniel Rogers House is being restored to become the new Bridgehampton Historical Museum. It will open, hopefully, in 2015.

The tollhouse on the Bridgehampton-Sag Harbor Turnpike
The tollhouse on the Bridgehampton-Sag Harbor Turnpike, Photo: From the Collections of the Suffolk County Historical Society

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