There are cultural and historic reasons why Halloween is sometimes called “Gay Christmas.” Before Pride became a worldwide movement, October 31 was the one day of the year where LGBTQ2S+ people could dress up and be who they wanted to be with a greater sense of freedom and without fear. When everyone is wearing outrageous “anything goes” costumes, there’s more room for queerness.
Such opportunities are sometimes rare. In many jurisdictions around the world, there have been laws prohibiting wearing clothes not traditionally associated with your gender—think men in dresses and women in suits. Wearing the wrong clothes could get you thrown in jail, or worse.
As author Randy Shilts writes in The Mayor of Castro Street, his biography of assassinated member of the San Francisco Board of Supervisors Harvey Milk: “One evening a year, like a chapter from a Cinderella story, the police would bestow a free night on homosexuals. Halloween has been staked out years before as the homosexual high holidays; gays did, after all live most of their lives behind masks.… For that one night, the police let homosexuals roam the city freely, even if they wore dresses.”
This excitement for Halloween continued even after Stonewall gave birth to the modern LGBTQ2S+ rights movement. In Armistead Maupin’s 1978 novel, Tales of the City, which captured the spirit of San Francisco in that era, he describes the “Halloween madness of Polk Street,” complete with gay men dressed up as roller-skating nuns. Scary? No. But fabulous, definitely.
The relationship between LGBTQ2S+ culture and Halloween continued into the 1980s, extending into horror movies. In 1985’s A Nightmare on Elm Street 2: Freddy’s Revenge, teen Jesse, who seems to be exploring his sexuality, has to battle knife-gloved, blood-spilling Freddy Krueger. The movie hit theatres as U.S. President Ronald Reagan first mentioned AIDS publicly.
Halloqueer themes pervade films like 1983’s The Hunger, with its love affair between Catherine Deneuve and Susan Sarandon; Gothic-drenched Anne Rice vampire novels like Interview with a Vampire; and the Abercrombie-level shiftlessness of David DeCoteau’s horror movies in the early 2000s. More recently, series like Mike Flanagan’s The Haunting of Hill House and The Midnight Club and the Duffer Brothers’ Stranger Things have toyed with the creepy and the queer.
None of this has been relegated to history. At a contemporary Halloween celebration, you might still see nuns on roller skates, along with horror movie–quality costumes and socially relevant get-ups.
Fred and Jason’s Halloweenie (October 25, 2024, Academy LA, 6021 Hollywood Blvd., Los Angeles) is billed as the largest, loudest and sexiest annual gay Halloween fundraiser in the region. Palm Springs’ Halloween on Arenas Road (October 27, 2024, Arena District, Palm Springs) sees an entire LGBTQ2S+ neighbourhood transform into a costumed extravaganza. There is also the free-to-watch Haunted Halsted Halloween Parade in Chicago’s Boystown neighbourhood.
Here are five more LGBTQ+ Halloween parties to check out this October in Canada and the U.S.
Provincetown, Massachusetts
Spooky Bear Halloween (October 31 to November 3, 2024). Situated on a protected bay on the northern tip of Cape Cod in Massachusetts, Ptown is steeped in New England folklore, from the ghosts of pirates and sorrowful widows of lovers lost at sea, to Indigenous lore and witchery. It’s only 80 kilometres as the spirit flies to Salem, site of the infamous 1692 witch trials. The multi-day, multi-venue festival is presented by the Northeast Ursamen, a non-profit organization providing bears and ursaphiles with opportunities to socialize in a “safe den,” includes parties, costume balls and dances, and a haunted house. Many of the events are centred around the Crown & Anchor (247 Commercial St., Provincetown), a hotel and entertainment complex, which is hosting a Spooky Bear Drag Brunch, Spooky Bear Bingo and Spooky Bear Halloween Ball.
Toronto, Canada
Halloween on Church (October 31, 2024, Church Street, between Gloucester and Wood streets). With LGBTQ2S+ roots dating back 50 years, when costumed partygoers were sometimes pelted with eggs as they entered any of the city’s few queer bars, Halloween in Toronto has grown into an annual event that attracts costumed revellers and their camera-carrying admirers). Wade through the radius-to-ulna packed crowd if you dare to take in the inventive costumes. Last year’s included a bat-carrying killer wearing a rabbit-headed mask fashioned from burlap, a Barbie doll still in its pink box and a by-the-power-of-Grayskull He-Man complete with sword, blond locks and furry loin covering. Several bars and clubs in the Village will host events during the weekend leading to Halloween night.
Philadelphia, Pennsylvania
Henri David Presents: Halloween the Ball (October 31, 2024, Kimmel Center for the Performing Arts, 300 S. Broad St., Philadelphia).
The longest-running Halloween tradition in the City of Brotherly Love has been celebrated for more than 50 years, attracting costumed guests and voyeurs looking for a bit of scary eye candy. Lookie-loos pay more than costumed goers to attend—US$75 instead of US$2—so you know those outfits must be worth seeing. Prize categories include best comicbook character, sensual fantasy, celebrity look-alike, most horrifying and the most unique couple.
While many costume-goers go all out to win a prize, it’s the host of the night, local jewellery designer Henri David—aka Philadelphia’s Mister Halloween—who always generates the most anticipation for his over-the-top costumes. David told Philadelphia Magazine in 2018 that the wildest costume he’s seen at his party was the John F. Kennedy Jr. plane crash: “A group of 20 people came as the crashed aircraft, with JFK Jr. hanging out of the window, dead. It was awful. And wonderful.”
Wilton Manors, Florida
Wicked Manors (October 31, 2024, Wilton Drive N.E. 21 St. to the N. Dixie Highway). Florida Governor Ron DeSantis might already scare the bejeezus out of you, but the LGBTQ2S+ community in the city of Wilton Manors and neighbouring Fort Lauderdale will turn the tables with its annual all-accepting and fright-filled block party. The theme for 2024 is Island of Misfit Toys, taking inspiration from the classic Rudolph the Red-Nosed Reindeer holiday special where children’s toys with strange quirks are exiled—a great subject to mine for inspiration for unusual, bizarre and freakish costumes. Hosted by The Pride Center at Equality Park (2040 Dixie Hwy, Wilton Manors), which supports and advocates for the rights and well-being of queer individuals, Wicked Manor also features a family trick-or-treat pre-event and gives out prizes for the best costumes.
New Orleans, Louisiana
Halloween New Orleans (October 18 to 20, 2024; Gallier Hall, 545 St. Charles Ave., New Orleans; the Fillmore, 6 Canal St., New Orleans; and other venues). Already famous for its annual Mardi Gras celebrations, NOLA deserves to be equally as famous for its four-day Halloween New Orleans celebration, which sees a series of events and fundraisers, all dipped in the scene-setting, moss-dripping Southern gothic atmosphere Louisiana is famous for. This was, after all, one of the settings Anne Rice used in her homoerotic book series, The Vampire Chronicles.
With a 2024 theme of “camp,” this year’s events include the Lazarus Ball at Gallier Hall, a black tie–preferred event that benefits the Lazarus Project, a home in New Orleans for men and women living with AIDS. Other events include a Saturday night Camp HNO at the Fillmore, a dance party where costumes are mandatory, and a Sunday Tea Dance. And this being the Big Easy, the Halloween celebrations are sure to spill out onto the streets of the historic French Quarter and along the banks of the Mississippi River.
