Formerly at 27-31 West 28th Street; sometimes referred to as 1185 Broadway was the New Fifth Avenue Theater. Eleanor Duse was known to have relations with both men and women. The legendary Italian actress had her New York premiere at this theater. In 1909, Duse retired from acting, and near to that same time she met and became involved in a lesbian affair with Italian feminist Lina Poletti, a former lesbian lover to writer Sibilla Aleramo. The two lived together in Florence, Italy for two years before ending the relationship.

On this site, in 1869, Edwin Booth opened a grand theatre to a design by Renwick & Sands in the Second Empire style. It was operated under the direction of actor-manager, Sarah Bernhardt. Bernhardt had relationships with both men and woman, most notably to Louise Abbéma. Eleanor Duse also premiered here.

Harry Miner's Eighth Avenue Theatre marked the uptown expansion of his theatre chain. The idea of the "chain," which he originated and which was later duplicated by others, allowed transfers of complete productions between theatres. After Miner's death in 1900, his sons managed his empire. In 1902, the theatre burned down and was rebuilt. Later, it offered movies and burlesque, ending its life as a movie house. Noted female impersonator Julien Eltinge was associated with this theater and was a fave in Miner’s chain of theaters.

Abbey’s Park Theatre was built in 1874 for Dion Boucicault. The theater was associated with Lilly Langtry. Langtry's lesbian affair with writer Natalie Clifford Barney is recorded in her novel "Idylle Saphique", published around 1901.

From 1966 to 1971, Asociación de Arte Latinoamericano operated a 74-seat theater in a small loft space at 682 Sixth Avenue, an eight-story building in Chelsea.

The Irish poet and dandy Oscar Wilde stayed at the Grand Hotel for a few days here while on his expenses-paid tour of America in 1882. In the late 19th century, when the theatre district moved further uptown, the Grand Hotel suffered from the loss of those patrons.

The exquisite Queen Anne style Hotel Chelsea, erected in the 1880’s, is associated with any number of people of LGBT interest - almost 100 years before Stonewall Riots. Actress Sarah Bernhardt who made a point of her bisexuality resided here soon after the building opened. Beginning in the ‘30’s, composer/critic Virgil Thompson lived here for over half a century, presiding over a largely gay salon of modern composers including Ned Rorem, Samuel Barber, Aaron Copland, Marc Blitzstein, Lou Harrison, Leonard Bernstein and John Cage. After WWII, the hotel became associated with a great many “renegade” writers , many of them LGBT, such as William Boroughs, Alan Ginsberg, Paul Bowls, Frank O’Hara, Gore Vidal and Tennessee Williams. The painters Frida Kahlo known for her affairs with both sexes, also spent time here. The ‘Portrait of Jason’ a seminal documentary by Shirley Clark about the struggles of an African-American gay man was filmed at the hotel in the years just before Stonewall, as was Andy Warhol’s “Chelsea Girls’ featuring trans superstar Holly Woodlawn. Ironically, Warhol’s would-be assassin, Valerie Solanas, lived here for a time as well. Rock icon Janice Joplin, also bisexual, lived here. Writer Eileen Myles lived here for many years and has written extensively about it. Filmmaker Howard Brookner and author Brad Gooch lived here together.

The London Terrace apartment complex encompasses an entire city block in the Chelsea neighborhood. Built in 1929 to a design by Farrar & Watmough for Henry Mandel, it has had many famous residents over the years. Some of its notable LGBTQ occupants included Susan Sontag, Annie Leibovitz, Kate Pierson (of the B52’s), Harry Kondoleon, Félix González-Torres, and Howard Brookner. In the 1990's, several noted LGBT politicians also lived there.

Lucien Carr once lived at 149 W 21st Street.

From about 1959 to 1968, the Mattachine Society of New York, an early and leading American homophile group, was based out of the Chelsea neighborhood.

The Church of the Holy Apostles met here before moving to 348 West 14th Street. The Chelsea Gay Association also met here.

From 1959 - 1963 The Living Theatre, directed by Judith Malina and Julian Beck, occupied floors two and three. Merce Cunningham had his dance studio on the top floor, which is where Robert Dunn taught the composition classes that launched the Judson Dance Theater. In 1977 Peter Saul, who once danced in Merce’s company, taught ballet classes in this studio. One of the studios in this building was the site of the first post-Stonewall gay and lesbian dance. That was 1970 and the dance was held by the Gay Liberation Front (GLF) at a place called Alternate U. The Gay Liberation Front formed in July 1969 and used Alternate U. as the location for many of its meetings and social events.

Bayard Rustin lived at Penn South from early 1960s to death in mid 1980s.

The National Gay Task Force Headquarters was formerly 80 5th Avenue at the intersection of 5th Avenue and 14th Street.

4 West 14th Street was home to the second location of Danceteria which had a sizable LGBT following. The club was co-founded by activist and Stonewall activist, Jim Fouratt, who who was also one of the founders of the Gay Liberation Front. It catered to a diverse after-hours crowd coming from the downtown rock clubs and gay discos.

Former location of the bar Private Eyes which was at 12 West 21st Street. It had a large LGBT clientele and had certain nights geared towards them. In its early days, Madonna, who had a sizable LGBT following. was a frequent guest.

Formerly located at 515 West 18th Street, The Roxy opened in 1978 as a roller skating rink and disco. It morphed into a gay dance hall on Saturday nights which was frequented by the likes of Madonna, Cher, Bette Midler and Beyoncé Knowles, holding up to 2,300 people at a time. The club closed in 2007.

First built c. 1869 as First Free Will Baptist church, the building was converted by James Everard to become a Turkish bath club in 1888. In 1916, the Everard's Baths once again became a male-only domain. By the 1950's, the Everard Baths became a meeting spot for homosexuals at a time when gay bars were illegal.

The Women's Liberation Center was located at 243 West 20th Street in a former firehouse. The Lesbian Switchboard, a hotline for lesbians seeking information and support, was run out of this building for many years. When Chelsea was still a dicey neighborhood, the center had the advantage of being across from the 10th Precinct which kept any mischief at bay. Despite being a major counterculture location, the police remained respectful of them. As Chelsea prospered, New York City decided that they wanted to sell off their properties and it was resold to a women's nonprofit.