On Saturday morning, when the Long Island Rail Road celebrates the 180th anniversary of the first train to reach Greenport, there will be pomp and circumstance, speeches from elected officials and an air of celebration.

The event aims to recreate that pivotal Saturday, July 27, 1844, right down to a brass band and a “wheeler” riding a Victorian-era high wheel bicycle around the village. Guests are encouraged to dress in Victorian- era clothing if they have any.

Back in 1844, “flags and streamers were flying in every direction,” according to a firsthand account published in the Brooklyn Eagle newspaper. “The population were out en masse — old men and matrons, young men and maidens, with a plentiful sprinkling of children, thronged the grounds.” 

Guests included “the Terrys, the Tuthills, the Hallocks, the Lathams, the Browns, the Paynes, the Youngs, the Racketts … the Conklins, the Griffins, the Hortons [and] the Booths,” reads another historic account preserved at Floyd Memorial Library in Greenport.

“Some came from Orient, until recently before known as Oysterponds. Others came from Oysterponds Point and from Plum Island, beyond the Gut. From across the harbor on Shelter Island they came, and to and from Sag Harbor.”

As the train pulled into the station, the Brooklyn Eagle reporter described a crowd astonished by an “iron horse, with lungs of brass and sinews of steel, [that] came dashing on at a furious rate, puffing volumes of smoke and flame from his nostrils … the wild fowl, startled from their banquetting in the creeks and tributaries of the Peconic, arose high in the air, careened in ominous circles above the monster … and then, with a fearful scream, took their departure.” 

Despite the notable celebration, it would be years before many North Forkers would make peace with the “monster” the railroad had let loose in their midst.

At the time of the station’s opening, most North Fork farmers had no interest in a railroad and the railroad owners had no interest in farmers, according to Don Fisher, historian and curator of the Railroad Museum of Long Island in Greenport.

“The North Fork was all agriculture, from the Sound to the bay,” he said. “These people had an economy out here — working hard and making good food, just like we do now. Back then they were growing produce and putting it on ships to Connecticut and trading with the South Fork. This was very, very good land.”

The sole goal of the railroad owners — a dozen New York industrialists who pooled their money with backing from silent European investors — was moving freight and passengers between New York City and Boston, through Greenport, as quickly as possible.

“They didn’t give a rat’s tail about the people living on Long Island,” Mr. Fisher said in an interview this week.

In the 1830s, attempts to build rail lines along the Connecticut coast up to Boston failed for two reasons: the type of durable cement used today hadn’t been invented yet, so the railroads couldn’t cost-effectively build solid bridges across swamp land, and even if they could have, Mr. Fisher said, the wealthy farmers along the Connecticut coast weren’t interested in selling land to the railroads.

“They had their own economy up there, and it was very hard to envision a railroad that would go from New York to Boston like Amtrak does today,” he said.

Once the North Fork station was established, the most efficient commute from New York to Boston was by train from New York City to Greenport, then steamer ship from Greenport Harbor to Stonington, Conn., and from there by train on to Boston. For a few good years, thanks to the new Greenport station, the LIRR dominated the New York-to-Boston market.

Meanwhile, up and down the Eastern seaboard throughout the 1830s and 1840s, small groups of investors were building tiny rail lines — 15- to 30-mile routes, what Mr. Fisher described as “links on a chain” that led to larger railroads consolidating smaller ones, just like the Greenport investors had done.

“This was an exciting time in America,” he said. “Once [the railroads] got rolling, they were moving people, they were moving money, mail and commodities great distances for a little bit of money — very efficient — and what once would take days was now taking hours.”

But the railroad and the North Fork farmers didn’t get off to a very good start.

The LIRR construction crews met little resistance as they laid tracks through the mostly uninhabited center of Nassau County and deep into Suffolk’s pine barrens, but when “they get to Riverhead, now they get some blowback,” Mr. Fisher said, “because we’re getting into this fertile property.” 

At first, many farmers were eager to sell or lease the 50- to 75-foot-wide easements required to run tracks through their fields — but they had no idea just how disruptive the actual trains would be. 

Soon enough, it was all too clear.

“As the train comes along, blowing its horn and chugging and steam coming out of it and making all this rattle-trap noise going from Riverhead to Greenport, it disturbs the farmers’ peace and quiet,” Mr. Fisher said. “Cows get so upset they literally stop milking. The chickens stop laying eggs and the farmers — they’ve got this belching thing going through [their farmland] and it’s spitting out wood chips from the fire, and it’s starting fires along the tracks. It’s burning up the corn. It’s doing all kinds of damage.

“Now that really pisses people off,” he continued. “The soot and dirt gets on Farmer Jones’ underwear and bedclothes that his wife has hung out, and now, all of a sudden, the peace and tranquility of the North Fork has been disturbed. The farmers took the money — they were cool. But they didn’t know what they were getting into. This [railroad is] running up and down [Long Island] and because it’s recognized by the state — these are powerful people, they’re making a lot of money — it’s a big business.

“It’s just like it is today with the building of hotels and motels out here, right? It’s — I don’t know if it’s progress — but it’s change.

“Now the farmers are in the middle of this, and the people — they can’t stop the train, so they revolt. 

“They start taking out a piece of track [to cause derailments], they’re going out and greasing the tracks” so that the steel wheels lose traction. “They would rob [the steam-powered engines] of wood or water so they couldn’t get to the next station … It was really passive-aggressive stuff.”

There was more peril ahead.

“One of the things that really upset the farmers in the beginning was their cows. They never thought of putting up fences, except maybe between [neighboring] farms, so the cows would just go across the tracks to the other side of the pasture — until the first cow got hit by a train,” Mr. Fisher said.

“Now the farmer is really upset, screaming bloody murder, ‘you’ve destroyed my cow.’ Let’s say a cow is worth $100. So the farmers screams at the railroad bosses and they say, ‘alright, listen, we’re sorry we hit your cow. You really need to put some fencing up, but we’re going to pay you $100 to make it right.’

“Well, it didn’t take too long before the farmers figured out if they had an old nag of a cow that was near time to be put to pasture and done away with because it wasn’t milking and it was getting old? ‘We take that old cow up and tie it on the tracks, the train will hit the cow, and we can put in a claim, and we’ll get $100 for a cow that was worthless.’ This is the kind of shenanigans that went on — and thus was developed, the ‘cow-catcher,’ because the railroads got wise to this.” 

A cow-catcher is a V-shaped device fitted to the front of 19th-century trains to deflect obstacles on the track that could derail or damage the train.

“These trains didn’t go too fast, so it worked,” Mr. Fisher said.

As this drama was unfolding across the North Fork, rival railroad pioneers had succeeded in building the Connecticut coast train line, which carried passengers directly from New York City to Boston in 11 hours. That strangled the LIRR’s growth strategy, and by 1850, the railroad was broke.

“From 1850 until the MTA was formed [in 1965], the Long Island Rail Road bounced in and out of receivership,” Mr. Fisher said. “They’d go bankrupt. They’d get money. They’d reassemble themselves, just like corporations do today.”

Soon enough the farmers began using the trains to bring fresh crops to New York City, and for a time, the railroad helped turn Greenport into a boomtown.

“When we talk about the acceptance of the railroad, one of the things that we have to keep in mind is the number of people that got jobs selling tickets, dealing with freight, the early postal railroad, all that stuff,” Mr. Fisher said.

The LIRR “made this island, because now that you had a train that ran out to Greenport, that ran out to Port Washington, that ran out to Patchogue. People could leave the confines of New York City … and build and establish communities further out. It really was the railroad that populated this island and made it possible for dad to live out toward Huntington and commute in to the city and work in Manhattan, or work along the shore front of the East River. And now mom and the kids are living in a much healthier rural environment. They got better air. They got a better environment. They got better food.”

This weekend’s celebration begins at 10:45 a.m. at the Railroad Museum of Long Island at 440 Fourth St. in Greenport. At 11:30, local officials will speak alongside LIRR president Rob Free, and at noon a historic marker commemorating the milestone will be unveiled. The entire four-acre site is listed on the New York State and Federal Registry of Historic Places.

For more information about how to get tickets to ride the ceremonial train out to Greenport on Saturday, visit the MTA’s anniversary tour website at away.mta.info.