My Queer Across America roadtrip has brought me to Chicago for the first time! After a 20-hour train ride from Denver, I arrive in the Windy City ready to check out Boystown and the Leather Archives & Museum.
I wander around the north side of Chicago, known as Boystown for the vibrant gay community. Despite the name and it being a notorious “gayborhood,” Boystown is more queer than anything else. An assortment of genders, non-genders, and identities give the city even more personality than the beautiful murals painted on the walls.
The area is filled with queer bars like Roscoe’s, Kit Kat, and Hydrate. I’m interested in something a bit more low key, so I pop into Replay, a video game-themed queer bar with a massive patio, craft beer, and, of course, plenty of video games ranging from retro Ms. Pac-Man to Ultimate Smash Bros.
After a couple of local Goose Island beers, I return to wandering around the Lakeview area. All along the street are towering bronze pylons with pictures engraved onto them. Looking further into the art pieces, I’ve learned that they are part of Chicago’s Legacy Walk, a recognized historical landmark that memorializes queer icons and events like Frida Kahlo, the Pink Triangle, and Sylvia Rivera. Each year, coinciding with National Coming-Out Day (October 11), new memorials are added.

It makes me so happy to see our history not only preserved but connecting with our present by being amongst the queer bars. I feel like queer areas either emphasize partying and nightlife (bars, clubs, bathhouses) or education (LGBTQ+ centers, trans resource organizations, health centers).
Maybe an intoxicated twink will wander out of a bar, read a couple of sentences about someone that paved the way for us to inhale poppers and shake our asses, and actually (gasp!) learn something.
I make my way to the Leather Archives & Museum. I’m nervous going up the steps to the surprisingly prominent building. I hadn’t been to a lot of leather events in my queer life because I never really felt accepted in those spaces. Leather culture typically values hyper-masculinity, and nothing about about my body or personality screams “masculine.” I’ve actually been discriminated against a few times at leather bars in LA. Bartenders often ignored me or charged me extra while catering to my bear friends.

However, I never want to miss a queer museum. So, I take the chance of going into the LA&M, and I’m grateful that I did. Unlike the leather bars I’m used to, the museum is spotlessly clean. There are a variety of sections in the exhibit dedicated to all sorts of fetishes: ropes, bondage, BDSM, voyeurism, chastity.
What I find most interesting is how women in leather and trans folks are prominently displayed throughout the exhibition. Like Mistress Mir, the “First Lady of Dominance,” who has been active in the BDSM community (and still is) for over 45 years, and the Lesbian Sex Mafia, a women and trans-inclusive community of kink.
The leather community has often excluded people that aren’t cis males. I’ve bartended kink events that denied entry to trans and cis women. The most common complaint in bathhouse reviews is pointed at the discrimination toward trans men. It’s surprising to see trans folks and cis women highlighted in the museum. This shows the importance of preserving our queer history.

The leather and kink community has waned since the ’80s because large parts of the community refuse to be inclusive of body types, genders, and identities. The definition of “masculinity” has also evolved. In order for the leather community to continue it’s incredible legacy, it needs to stop gatekeeping.
The beer courses through my body, so I head to the nearest restroom. In a comical ode to cruising culture, the walls are covered with phone numbers, social media handles, and obscene drawings.
Chicago is one of the most inclusive cities I’ve been to on my Queer Across America road trip, and there will never be enough time to explore everything the city has to offer. If you’re ever traveling to Chi-Town, do yourself a favor and stay for more than a few days!
Continue with me on my Queer Across America adventure next week when I pay homage to the grave of Brandon Teena, visit the LGBTQ+ archives, and explore the surprisingly queer-friendly state of Nebraska.
Photos courtesy London Alexander and social media
