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On June 28, 1913, a young woman from Cutchogue named Madaline Fleet treated some friends to an evening at the Orient Point Inn, where they took photos and explored the stately four-story hotel’s waterfront grounds. Later, the group enjoyed dinner by the shore and danced to what the County Review, a predecessor to the Riverhead News-Review, described as “the strains of lively music.”

“From all the glowing accounts,” the report continued, “we are sure that ‘Mad’s blowout’ was an occasion long to be remembered by her friends.”

At the height of its popularity near the turn of the 20th century, outings like ‘Mad’s blowout’ were typical at the Orient Point Inn, an establishment built in 1672 and abandoned 300 years later.

Originally constructed as a residence at the tip of Orient Point, the structure is believed to have housed British troops during the Revolutionary War.

“I’m sure [the owners] didn’t volunteer the house,” said Amy Folk, collections manager at Oysterponds Historical Society in Orient. “It was taken over for quartering.”

According to “Hotels and Inns on Long Island’s North Fork,” a book Folk co-authored with former Southold Historical Society director Geoffrey Fleming, the house was “formally turned into a stop for travelers” in 1834. Its owner, Jonathan Fish Latham, named it Orient Point House and enlarged the building to accommodate guests traveling to and from Connecticut.

After Mr. Latham died in 1853, the hotel had a succession of owners. Anna Brownson purchased it in 1860 and gave it to her niece Elizabeth Parsons two years later.


Around this time, Folk said, vacations were becoming increasingly available to the middle-class. With the Industrial Revolution and prevalence of machines, the everyday person’s desire for leisure grew — as did their longing for a seaside respite from the stiflingly hot New York City air.

“Tourism was becoming something everyone could do,” Folk said. “By the 1870s, we had enough labor-saving devices that the average person could get out of the city.”

The Orient Point Inn, meanwhile, “developed a reputation for fine dining and comfortable rooms and was becoming popular with hunters, fishermen and visitors looking for solitude,” according to Folk’s book.

A number of notable guests are said to have stayed at the hotel at various points in its history, including poet Walt Whitman, who was a frequent visitor to the North Fork, and President Glover Cleveland. Novelist James Fenimore Cooper is believed to have written one of his final books, “The Sea Lions,” while lodging there.


The Orient Point Inn again went through a series owners until 1922, when it was purchased by Eugene McDonnell. The Great Hurricane of 1938 tore off part of the building’s roof and extensive repairs were made.

Sometime in the 1950s, business changed drastically at the inn when New York State mandated that all hotels larger than one story have a steel-reinforced frame. The Orient Point Inn had a timber frame that “would have been a nightmare to retrofit,” Folk said. Rather than comply with the mandate, Mr. McDonnell opted to shut down the hotel.

The inn’s restaurant remained open until at least 1965, the last year dinner specials appear to have been advertised in local newspapers. By 1970, however, the entire structure was abandoned and had begun to collapse on itself.

In 1973, the Long Island Traveler reported that a real estate developer planned to develop condominiums on 35 acres adjacent to the old hotel. These efforts were staunchly opposed by a group of local residents who called themselves the Committee to Save Orient Point and were “prepared to sue to prevent Southold Town Planning Board’s approval of an application by Land’s End Realty,” the Traveler reported.

Later, in 1981, The New York Times reported that six Manhattan investors had purchased the tip of Orient Point for $2 million in order to “make way for condominiums.”

Those plans never materialized. Instead, the once-elegant Orient Point Inn was demolished by the local fire department.

Today, the site is part of a park.