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New York City’s historic private clubs are a vestige of an older world, and the rise of newer, hipper clubs like Norwood and Neue House, reflect a desire to expand the vocabulary of what a private club consists of. At Untapped Cities, we’ve been to a lot of these clubs for varying reasons – for events, for meeting, as members. In our first installment of this series on the city’s private clubs, we’re featuring 10 notable clubs among the city’s oldest that have stunning architecture and a rich history.

1. The Union Club (1836)

The Union Club is the oldest private club in New York City (but not the oldest in America). The grande dame of the private clubs, the Union Club is located in a landmarked building designed by Delano & Aldrich on 69th Street and Park Avenue, after two moves from downtown. Not surprisingly, the Union Club is known for its conservative slant and its policies were the reasons for the founding of rival clubs, The Knickerbocker and the Metropolitan Club later. The club is still in operation and counts Dwight D. Eisenhower, Winston Churchill, Ulysses S. Grant, and William Randolph Hearst among its notable members.

The Union Club has a website (unlike the Knickerbocker) but it’s for members only. Guests (and potential guests) can read about club rules and dress code (like no use or display of cell phones in common areas) here.

2. The University Club (1861)

The University Club, founded in 1861, forms an imposing corner along Fifth Avenue. Built when this Fifth Avenue stretch was filled with Gilded Age private mansions, it now forms a contrast with the luxury stores in its midst. The high windows prevent much peeking in but you may notice the smell of chlorine from the pool inside while walking by.

The first meeting of the University Club took place in 1861 at Columbia Law School, and the club’s charter was formed in 1865. Its first building was located at 26th Street and Madison Avenue. The Fifth Avenue club was built in 1899 by famed architects McKim, Mead and White. and the interiors, which include a grand ballroom and library, are beyond opulent. The University Club, unlike what its name may seem to imply, is not affiliated with the clubs of universities but the stately Harvard Club and Yale Club were both built in this same decade.

One of the tricks of the private club search is to stay as an overnight guest. The University Club has guest rooms on upper levels available for overnight stays.

3. The Lotos Club (1870)

The Lotos Club is one of the oldest literary clubs in the United States and counts Mark Twain, who called it “The Ace of Clubs,” a member. It has traditionally had a more inclusive outlook, including Ladies Days starting in 1872 before women were allowed. Its “State Dinners” have played host to U.S. Presidents, explorers like Amelia Earhart, artists like Leonard Bernstein and Roy Lichtenstein and even athletes like Joe DiMaggio.

The current building on East 66th Street was a mansion built for the daughter of William H. Vanderbilt. The Lotos Club was originally located on Irving Place and moved several times.

4. The Knickerbocker Club (1871)

The Knickerbocker Club, located on East 62nd Street, was founded in protest against what were seen as the declining standards of The Union Club. J.P. Morgan was a member until he resigned in protest because his friends weren’t admitted, and started the Metropolitan Club. It remains one of the most elusive of clubs, though often mentioned in popular culture, and continues to lack a website. It also remains male only.

5. The Salmagundi Club (Founded 1871)

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Art is alive and well at The Salmagundi Club, founded in 1871 and one of the oldest art organizations in the U.S Its current location at 47 Fifth Avenue was built in 1853 as the residence of the president of the Pennsylvania Coal Company and in 1917, The Salmagundi Club purchased the mansion where it has resided ever since. The building was designated a Historical Landmark in 1969 and placed on the National Register of Historic Places in 1975.

In 2014, the brownstone underwent a major restoration adding more grandeur to the large gallery halls that form the majority of the club. In addition, there’s a tap room downstairs and smaller meeting rooms upstairs. The Salmagundi Club is one of the more affordable clubs, at only $247.50 per year for junior members (under 35) and patrons who support the arts. The Salmagundi also has reciprocal memberships with clubs like The Players Club, The National Arts Club, as well as clubs around the world.

See more photos inside the Salmagundi Club.

6. The Grolier Club (Founded 1884)

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Nestled among the beautiful townhouses of the Upper East Side is the Grolier Club, a private club dedicated to the book arts. Founded in 1884 and named for the great French Renaissance bibliophile Jean Grolier, the club hosts eight exhibitions per year. Though the club is private, and membership is by nomination, the exhibits are free and open to the public.

The Grolier Club’s mission, as stated in its constitution, is “to foster the study, collecting, and appreciation of books and works on paper, their art, history, production, and commerce.” Since its inception, the club has maintained a collection of books about books, the history of printing and publishing, author and subject bibliographies, exhibition catalogues, rare books and illuminated manuscripts. The library currently holds over 100,000 volumes.

See more photos inside The Grolier Club here.

7. The Montauk Club (1889)

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The Montauk Club was founded in Park Slope in 1889, reflecting the move of New York City’s influential to Brooklyn. The Venetian Gothic building designed by Francis H. Kimball marks a unique architectural style, compared to the Neoclassical inspiration of many of the other social clubs in New York. The Corduroy Appreciation Club holds its annual meeting and party there annually on 11/11 (because the date resembles the physical look of corduroy) and the club is a popular set for films and television shows.

8. The Metropolitan Club (Founded 1891)

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The Metropolitan Club, located at 1 East 60th Street on the corner of 5th Avenue,was founded in 1891 by J.P. Morgan to challenge the Union Club, which had rejected some of his new money friends. Each member, which included Vanderbilts and Whitneys, contributed $5,000 to buy the plot of land where the club stands today in its marble-clad grandeur, designed by Stanford White. The building was described in the New York Times in 1892 as “a clubhouse the equal of which does not exist in this country or in any other.” The final price tag for the Metropolitan Club was reported by the Finance and Building Committee to be $1,777,480.20 (valued at just over $48 million adjusting for inflation).

Located uptown when many clubs were still downtown, the Metropolitan Club had all the amenities: dining hall, a breakfast room, smoking room and three large private dining rooms. There were 22 suites for overnight guests, a bowling alley, wine rooms and, most innovative of all, a ladies’ annex. Even a generator to keep proper heat and cooling throughout its many halls and dormitories.

See our photos of the opulent interior of The Metropolitan Club.

9. The Players Club (Founded 1899)

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In 1888, Edwin Booth, brother to the infamous John Wilkes Booth, founded The Players Club at 16 Gramercy Park South together with fifteen other incorporators, including Mark Twain and General William Tecumseh Sherman. It was intended as a club where actors could socialize with the elite and elevate their status from rabble-rousers to artists.

Housed in a stately Greek Revival townhouse, The Players Club occupies four floors, plus the Grill and taproom in the basement. Appropriately, a theater is located on the main floor. A curious artifact is the bedroom of Booth on the third floor, which remains full of his mementos, exactly as he left it. Walking into the room, you can still smell the tobacco scent of smoke that clung to the wallpaper. One of his fans actually left his body to Booth after he died, and became the skull that Booth held in Hamlet’s famous soliloquy.

Our upcoming insider tour of the Players Club will be led by a docent from the organization and will include a visit to the Booth bedroom:

Insider Tour of the Players Club on Gramercy Park

See more photos of The Players Club here. The taproom is included in the book New York: Hidden Bars and Restaurants by Untapped Cities writers Michelle Young and Laura Itzkowitz.

10. The National Arts Club (Founded 1898)

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Located next to the similarly stately The Players Club, The National Arts Club is housed in the former Samuel Tilden Mansion. Founded in 1898, the National Arts Club moved into the Tilden Mansion in 1906 from its original 34th Street location when a larger premises was necessary. The club counts three Presidents–Theodore Roosevelt, Woodrow Wilson and Dwight D. Eisenhower–in addition to the numerous painters, sculptors and architects that have formed its ranks.

The mission of the National Arts Club is to “stimulate, foster and promote public interest in the arts and educate the American people in the fine arts.” These days the club serves multiple functions for members and non-members. There are two galleries for rotating exhibitions, a dining hall with a great prix fix lunch menu and dinner, a bar, and multiple lounge areas. There are numerous subcommittees dedicated to various fields of art, including architecture, film, culinary, fashion, theater arts, literary, music and archaeology. There’s also a Young Members Committee.

See more photos of The National Arts Club here.

Bonus: Explorers Club (Founded 1904)

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The Explorers Club was founded in 1904. Located on the Upper East Side, the gothic building that houses The Explorer’s Club is filled with artifacts from explorations by its founders and members, including Teddy Roosevelt, Neil Armstrong, John Glenn, and Edmund Hillary. The club is dedicated to scientific exploration and research and is open to field explorers, those that support its mission, teachers and students. Joining as a student or teacher is one of the most affordable ways to join a social club in New York City, though you need to be sponsored by a current member and have an interest in pursuing exploration or field science as a career.

See photos from our exploration of The Explorers Club.

Next, check out the Gilded Age Mansions Along 5th Avenue’s Millionaire Row. This article co-written by Michelle Young, Laura Itzkowitz, Lynn Lieberman and Phillipe Chatelain.