1.646.560.3205 andrew@oscarwildetours.com

Gay history in New York

Village Stonewall nyc oscar wilde

In the last few weeks, I’ve been planning a gay history tour of New York for the spring for Oscar Wilde Tours. New York is truly one of the great gay cities, along with London, Paris, Berlin, Florence, or Athens. Ever since the days before the Civil War, when Walt Whitman hung out with his Bohemian friends at Pfaff’s Beer Cellar at Broadway and Bleecker, it has been a major center of gay life.

It is true that the city often tried to repress it, but since the late 19th century, the city has had drag shows and gay baths and bars and cafés which, if not exactly gay, tolerated openly gay behavior—or even used it as an attraction for customers. And the city has been a mecca for gay people from other, more repressive parts of America and home to an astonishing list of famous and fascinating LGBT personalities and talents, from Whitman to Bessie Smith to Cole Porter, Rudi Nureyev, Andy Warhol, and so on.

Village-Wilde-House-oscar-wilde-toursSadly, New York does not make a cult of its own history, and many buildings that had a key role in the city’s gay history have vanished. But there is still plenty left, and some great sites are, as it were, hiding in plain sight. We all know, for instance, that the gay liberation movement really took off in Greenwich Village’s Sheridan Square in 1969, when the patrons of the Stonewall Inn responded to a police raid by rioting. But the Village has been the center of all of New York’s artistic movements and countercultures since Whitman’s time, so there are also lots of other historic things in the neighborhood, including places where a whole line-up of America’s LGBT writers have lived: Herman Melville (author of Billy Budd, America’s first great gay love/hate story), Edna St. Vincent Millay (the prototypical free—and bisexual—woman of the 20s), James Baldwin, Edward Albee, and so on.

But there is also more gay history right in the square itself. The theater at 1 Sheridan Square (now home to the Axis Theater Company) for example, is a gay history site several times over. In 1938 the space became a bar called Café Society, one of the rare places in the city where whites and blacks could mix, both on the stage and in the audience. Such places, known as ‘black and tans’, tended to also attract and tolerate a mixed audience in other senses, and Café Society—suggestively nicknamed “the right place for the wrong people”—was a hotspot for what were called “long-haired men, short-haired women, and those not sure exactly what they are.” There is a lot to tell about Café Society. The opening act, for instance, was an unknown singer called Billie Holiday, who made her name singing there for 2 years. Another singer in early years was Bayard Rustin, one of the great leaders of the Civil Rights movement—whose name is sadly not widely remembered because after his 1953 arrest for cruising, he was discriminated against both by opponents of Civil Rights and by the movement itself.

Café Society closed in 1950, but the theater’s gay history didn’t stop there. It was a gay dance club in the 1960s. And most importantly, in the 70s and 80s it was the home of Charles Ludlam’s Ridiculous Theater Company. Ludlam was one of the most important drag artists in American history; along with Andy Warhol, John Waters, and Harvey Fierstein, he is one of the people who brought drag shows into the mainstream, integrating drag acts back into the genres (theater and movies) that they parodied. This is where Ludlam’s plays were put on for over a decade, including his cross-over hit, The Mystery of Irma Vep, and it is also here that he gave Charles Busch, the leading drag artist in today’s theater, his first serious opportunities to perform.

And that’s just one address. New York’s gay history is richer and longer than you may have realized—as we’ll try to show on our tours….

October 28, 2026

We thoroughly enjoyed our trip through Italy with Professor Andrew Lear, who was a pleasure to travel with, and who provided fascinating insights about all the places we visited. Whether it was Ancient Rome, the Renaissance, or 1930’s Capri, it was like having access to the latest tea no matter how old the gay gossip was. We definitely saw places such as Paestum and Hadrian’s Villa that we would not have thought to go on our own, and gained new insights about places we had been to before but had not considered through a queer lens (even St. Peter’s Basilica at the Vatican!). Professor Lear also found us wonderfully knowledgeable local guides, and made sure we ate well throughout the trip. We appreciated his recommendations for additional things to see or eat during the unscheduled down times. We usually like to travel on our own, so this was our first organized tour group trip we had ever been on. I would say if you’re looking to go on an adventure, without all the fuss of planning, and want to experience a country’s highlights with a queer twist, don’t hesitate to book a trip with Oscar Wilde Tours!–Kenneth Hung

Avatar for andrew
andrew
October 9, 2026

This CMBYN northern Italy tour was my 3rd Oscar Wilde tour. That says something right there. First class all the way, from hotels, to food, to transportation, can’t ask for better. I was pleased that the premise of the tour was fulfilled as much as it could be. Fun to see the filming locations for the movie. But there was plenty else to “wow” us each day. I was gratified to obtain a ticket (through Andrew’s guidance) to attend a performance at La Scala (Milan) of “La Traviata.” And in Verona I got to attend a “popera” “The Hunchback of Notre Dame” at the Roman Arena. (Andrew facilitated those tickets.) Also outstanding were the architectual masterpieces of Andreas Palladio in Vicenza. And my first time in Venice proved to be quite eye-opening including a tour of St. Mark’s Basilica, and the Doge’s Palace. Excellent guides in each experience including our viewing of da Vinci’s “The Last Supper.” I could go on, but I won’t.

Avatar for Randall McNames
Randall McNames
October 8, 2026

Avatar for TestReviewer
TestReviewer
July 22, 2026

I have been hoping for an England tour from Oscar Wilde Tours for years and I was very excited to see that wish fulfilled. It did not disappoint at all. The tour could be called the great English literary tour as we went from Shakespeare (Stratford on Avon + The Globe Theatre London), A walking tour of Bloomsbury (London) and then the homes of Virginia & Leonard Woolf, Duncan Grant and Vanessa Bell, Knole and Sissinghurst for Vita Sakeville West and Harold Nicholson. Bath was the point for all of our Jane Austen segments with visits to the Pump Room for tea and an optional trip to the Theatre Royal where Jane placed bits of her novels (Northanger Abbey and Persuasion). For dear Oscar Wilde we visited his Tite Street Home in London, Brighton where he and Bosie vacationed, Oxford University and Magdalen college where Oscar studied . Then a trip to York and Halifax to see where the fascinating Ann Lister lived and loved and wrote her diaries. All this plus Blenheim, the Royal Pavillion at Brighton and Howards Castle for a bit of Peerage living. Also included were marvelous meals ,an incredible local guide who kept us all together (amazing for a group of 15 and not as easy as one might think) . We had enough free time in London to see several plays and museums on our own although we did have a few museum tours included (a particularly good tour of the V & A with a wonderful guide). If you want to visit England and not just London but also the beauty of the countryside, the stately homes and gardens while enjoying the company of a lively group of fellow travelers, I cannot recommend Oscar Wilde Tours highly enough. Andrew packs your days with fascinating information on the sites visited and the people who lived in those places. Believe it or not, this is just the highlights, there was much more and all of it made for a very memorable trip

Avatar for Glen M.
Glen M.

Travel through gay art and history with Oscar Wilde Tours.

Proceed Booking