However, the port of Sag Harbor was busier, meaning that the railroad would have more variables to deal with when it came to scheduling. Greenport was the most advantageous jumping-off point for passengers coming from New York City on their way to Boston. 

“We like to say, that Greenport was the reason for the Long Island Railroad,” said Don Fisher, president of the Railroad Museum of Long Island.

Greenport has a deeper, wider harbor that allowed steamships in and out to Connecticut more easily. Most importantly, to get to Sag Harbor, you had to go over Shinnecock Canal, which at that time was essentially a tidal swamp where water would pass between the Peconic Bay and Southampton Bay. 


“It was marshy, you would have had to bridge it over. That cost a lot of money. Also, you didn’t have the metallurgy and stuff in the early 1800s. That’s why we’re coming down Long Island anyway, because you couldn’t get across the rivers in Connecticut,” said Mr. Fisher. “At that point, we didn’t have the resources, knowledge, or the metallurgy to build bridges. We didn’t have the Portland cement to put proper piers to get across those rivers.” 

Before engineering advancements in metal and cement, it wasn’t possible to build bridges strong enough to support the weight of the trains. In order to connect points south with New England and create a corridor for both passengers and commerce, the Long Island Rail Road chose to run along the center of the island and up to Greenport. On July 27, 1844, the Greenport line began operation.

“And for five or six years, the Long Island Railroad, after it was formed, those people made a lot of money because it was the fastest way to get from New York to Boston. So you get on a boat, go across on a ferry boat to Brooklyn, you’d get on the train, and in three hours, you would be out there on the dock,” Mr. Fisher said.

Greenport had a four-bay engine house, a hostler engine, freight houses and a turntable. The train ran right out onto the dock so that boats could unload directly into the cars.

“They got fresh oysters from out here every day. You’re going to be sending out perishables, you needed to be able to ice them down. The oysters would be put into boxes or barrels at the time, and they put ice on top of their oysters to keep them chilled. The railroad made it not only economically feasible, but physically feasible to move these perishables, because you could put it on the train in less than three hours it was in the city,” said Mr. Fisher. “The truck would run up to the train depot there in Greenport, and they would ice in on top of the oysters and the fish and then transport the stuff in.”

The freight house serves as the eastern outpost for the Railroad Museum and the turntable is still there. The dock still stands, with the old station serving as the East End Maritime Museum. Ownership of the line has changed hands several times, first from the MTA to Suffolk County and then to the village of Greenport.

Sag Harbor eventually got its own railroad connection, but not until 1870 — more than two decades after Greenport’s line opened. The Sag Harbor branch served as the South Fork’s eastern terminus for 25 years until expansion pushed further east to Montauk in 1895.

The village’s station was rebuilt in 1909 and saw various uses, including transporting torpedoes to the wharf for testing during World War I. The branch was abandoned in 1939.

“The importance of Greenport cannot be downplayed because it was the reason for the law on the railroad,” said Mr. Fisher. “It was an important site for maintenance and preparing the trains to go back to the city the next day. It’s where the people could come and get on a train and get on their way to Boston.”

See more in the Keeping track of history series:

Wading River Station

Calverton Station

Manorville Station

Riverhead Station

North Fork stations

The post Keeping track of history: Why Greenport won LIRR race to the East End appeared first on Riverhead News Review.

Austin Corbin, who became president of the Long Island Rail Road in 1881, was an ambitious but difficult man. He is credited with consolidating the many small railroads that crisscrossed Long Island into a single, profitable entity. He also expanded the southern rail line all the way to Montauk by strong arming the Montaukett Indigenous out of nearly 10,000 acres of land. 

For a time, Mr. Corbin’s nephew, Fredrick Dunton, was in business with him at the LIRR as a physical engineer. There was even a station in Queens named for him. At some point, the two had a falling out, and Mr. Dunton left to begin his own venture: The Boynton Electric Bicycle Railroad. 

This experimental railroad was based on a diesel-powered bicycle train that Eben Boynton had run for two years from Brooklyn to Coney Island. These double-decker cars were able to accommodate 200 passengers per trip. The Long Island version was much smaller, with a single level, trolley-shaped car that only carried 24 people at a time. Construction of the first two miles was completed in 1894.

George Walsh, Trustee and archivist for Railroad Museum of Long Island, has been researching the Boynton Electric Bicycle train since he was 17 years old.

“The Boynton Electric Bicycle Railroad was a railroad that was supposed to run from the Bellport area to Rocky Point. And they constructed a car that was used on an experimental track in East Patchogue. That car was two-wheeled car, so that’s where you get the bicycle idea. Two wheels, and it ran on a single track. It could go 60 miles an hour, it had an overhead structure with wheels that kept it balanced, and it used a steam-powered electric generator,” said Mr. Walsh.

A man named George Hagerman, of Rocky Point, became a prominent investor. He owned the land that became Wardenclyffe, Pinelawn cemetery, and large tracts of land around Patchogue, among others. Mr. Hagerman was impressed with the original Boynton Train in Brooklyn, so when he found out about the electric version, he offered some of his land. He sold plots of land for $25 each to the railroad laborers, who were mostly Italian immigrants. 

“The game plan was to bridge the Great South Bay and put a hotel on Fire Island at Long Cove. And they were going to have ferries to go to Connecticut. The idea being to bring people from New England out to Fire Island,” said Mr. Walls.

Mr. Corbin, peeved that his nephew had left his business to go out on his own, refused to allow the Bicycle Railroad a right of way over his track. But rather than leaving it there, he wanted to make sure the monorail would not be successful, so he extended what was known as the Port Jefferson branch to Wading River and renamed it the Wading River Branch. He also did this with mostly immigrant labor imported from New York City.

“There was no reason to build a railroad out to Wading River. There was nobody living there. Mr. Corbin, in spite, said, ‘We’re going from Port Jefferson; We’re going to go to Wading River,’” said Don Fisher, president of the Railroad Museum of Long Island. “This was a good idea, really. Mr. Corbin wasn’t a stupid man. He was a vindictive man, possibly. He was going to make sure that his nephew and cohorts weren’t going to get up there. But he was also looking at continuing from Wading River into Riverhead. So then for the main line, which was built in 1844 to Greenport, there would be an escape route.”

Just as the construction of Manorville station and the spur to Eastport allowed for an escape route from the main line to the southern line, extending the northern track to Wading River and then eventually on to Riverhead would provide an additional route for trains to avoid trouble on the main line.

Not only was Mr. Corbin looking at cutting off the monorail’s north-south vacation route, but he was also thinking of the problems a more nimble electric monorail posed to his empire.

“Corbin realized that this thing was a threat to steam trains. The invention itself. The electric monorail. Ultimately, they could outperform the steam trains. Think of the Long Island Expressway, and think if in the center median, you have monorails,” said Mr. Fisher. “They would want to take the train, so this thing could go 60 miles an hour then, and that’s only because the track they had wasn’t long enough to go faster.”

Another quirk of fate related to the Wading River Station is Nikola Tesla and the building of Wardenclyffe. All of the material for the construction of Tesla’s tower came to the property via the Wading River branch. There was even a siding constructed on-site to drop off loads of timber. The railroad museum has letters from the LIRR asking Tesla to settle his $3,000 shipping bill, the equivalent of more than $100,000 today.

The Wading River Branch lasted until 1938, when the station and engine house were dismantled. The timber from the engine house was reused to build what is now the Village Beverage store. At that time, it reverted back to the Port Jefferson Branch.

“If it was here today, certainly because of the population centers that have grown up along the North Shore through that area, you would have people that would be using it to go to work, just as they leave Port Jefferson now … It would be used for that travel, [and] certainly would be used as they were promoting it back in the 1800s and the early 1900s,” said Mr. Fisher. “It would be a vacation line. Just as people now take the train to Greenport to go to Shelter Island, East Marion, Orient [and] Southold on the weekends, they would be using it to come out to their summer homes all along the Sound. If we were there today, I would almost bet my right arm, the Long Island Railroad in the engineers would have completed the line out to Riverhead.”

Other stories in the Keeping Track of History series:

Calverton Station

Manorville Station

Riverhead Station

North Fork stations

The post Keeping Track of History: Wading River Station appeared first on Riverhead News Review.

This is the first in a series on the history of train services on the East End, and the numerous changes the industry brought to Riverhead and the North Fork.

“It took them 10 years to go from the foot of the East River in Brooklyn to Greenport,” said Don Fisher, president of the Railroad Museum of Long Island in Riverhead.

The Manorville Station stop was originally called St. George’s Manor and opened in 1844. Local history holds that the first station agent, Seth Raynor, was a patriot from the revolutionary war. The story goes that he painted over the “St. George’s” because it reminded him of the king, leaving just “Manor.”

The stop was little more than a refueling station, since there was no town to speak of at that time. Woodcutters would cut timber and stock it next to the tracks, as these trains ran on wood and not coal. There was also a water tower to replenish the steam engine’s supply.

“It was important stop for them to pick up water and wood on their way to make steam to propel trains out to Greenport. Though it was a fueling depot … it also became an important station,” said Mr. Fisher. “Manorville was really just a clearing in the woods where the train would stop, take on water. The local people would sell them firewood.”

In 1869, Manorville station became the western end of the Sag Harbor branch, a line that was extended through Eastport to the south shore. This was to outmaneuver the South Side Railroad, which ran from Brooklyn to Patchogue and had planned to extend out the South Fork. 

“The Long Island Rail Road said, ‘Hey, we got to make a right hand turn here. We’ve got to get in front of the South Side Railroad so that they can’t proceed from Patchogue out to Sag Harbor.’ And that’s what they did,” said Mr. Fisher. The track ran through the South Fork towns and ended in Sag Harbor.

Manorville also featured a special feature of railroad engineering called a wye. It consists of a triangle of tracks with a switch at each corner, where an engineer can navigate around the triangle to reverse direction. 

“You can imagine a train coming along, going up the right-side angle to the top point,”said Mr. Fisher. “He stops his train, he backs on down to the left-hand point, which is going Greenport. Now the train is facing New York City. And you can go across the base of the triangle with your train and go all the way back to Ronkonkoma … [to] get back into the city. If you’ve got the acreages, the land, that’s very inexpensive to make those three tracks and build a wye.”

This feature allowed the railroad to operate what was known as the “Greenport Scoot,” a train that ran from Greenport to Manorville and then all the way to Sag Harbor.

“Manorville, at this point, was very important as a communications loop for people to go from the shipping and the whale industry out of Greenport to the shipping and whale industry down in Sag Harbor. You [could] go back and forth and you didn’t have to take a boat,” said Mr. Fisher. “That opened up all kinds of opportunities for families to move back and forth.”

The mail was carried by horse or stagecoach until 1908, when the Manorville Post Office opened near the train stop. Around this time, the station name officially changed to Manorville. 

The station building was torn down and replaced with a shelter in 1941, and by 1949 the branch was abandoned. In 1968 the stop was officially discontinued.

“It was very lightly used by the 1940s. Railroading is a business, and any place that they can save money and pare off maintenance costs, they’re gonna do it.” Mr. Fisher said. “I think today, in hindsight, they wish they had it.”

Other stories in the Keeping Track of History series:

Wading River Station

Calverton Station

Riverhead Station

North Fork stations

The post Keeping Track of History: Manorville Station appeared first on Riverhead News Review.

Photos by Jeremy Garretson

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This year’s focus was “Saving Railroading History.” Festival goers had the chance to get up close to toy trains in all scales, including a historic Lionel layout. They could also ride the restored 1964-65 World’s Fair park train. Additionally, there was food and live music, vendors and the “scoot” train to Greenport.

The post Just the ticket: Photos from the 2025 Riverhead Railroad Festival appeared first on Riverhead News Review.