Ep.48 / The Queer History of Halloween: Drag, Ghost Stories & Hillcrest’s Nightmare on Normal Street Ticket Giveaway
Halloween has always been more than costumes and candy — for the LGBTQ+ community, it’s a night of freedom, self-expression, and fabulous chaos. In this spooky and hilarious episode of Hot Air, host Josh MacLean dives into the queer history of Halloween — from the early underground drag balls to today’s massive LGBTQ+ celebrations in Hillcrest and beyond.
🎃 The Queer History of Halloween, Drag Ghosts, and Hillcrest’s Nightmare Giveaway
Halloween isn’t just about candy, costumes, and spooky decorations. For the LGBTQ+ community, Halloween has historically been much more — a night of freedom, self-expression, and unapologetic queer joy. From the underground drag balls of the past to today’s massive celebrations in Hillcrest, San Diego, Halloween has become a cornerstone of queer culture.
In this episode of Hot Air, host Josh MacLean dives into the queer history of Halloween, shares a terrifyingly fabulous drag ghost story from Provincetown, and announces a special giveaway in collaboration with Fabulous Hillcrest — your chance to win tickets to San Diego’s largest LGBTQ+ Halloween block party, Nightmare on Normal Street.
Whether you’re a fan of LGBTQ+ history, drag culture, or just looking for a spooky good time, this episode and blog post have something for everyone.
🏳️🌈 Why Halloween Became the Queer Holiday
Historically, Halloween has been one of the few mainstream holidays where queer expression was not just tolerated, but celebrated. In a time when LGBTQ+ folks often faced discrimination and invisibility, Halloween provided a safe night to experiment with identity, gender expression, and flamboyant creativity.
Costumes, drag, and gender-bending were not just fun — they were liberating. For one night, queer people could step into their full, authentic selves in public without judgment. Halloween became more than a party; it became a cultural touchstone, a form of queer expression, and, in many ways, a celebration of community resilience.
Even today, Halloween remains one of the most important holidays for the LGBTQ+ community. It’s a night to be loud, proud, and creative — and to honor the generations of queer people who paved the way for safe, visible expression.
🏙️ Hillcrest: San Diego’s LGBTQ+ Halloween Hub
If you want to experience the pinnacle of LGBTQ+ Halloween, look no further than Hillcrest, San Diego. Known as the city’s official queer neighborhood, Hillcrest is home to over 1,300 small businesses, bars, restaurants, and community spaces. When Halloween rolls around, the entire neighborhood transforms into a living celebration of queer culture and nightlife.
“Hillcrest doesn’t just celebrate Halloween, it becomes Halloween,” says Josh MacLean. “Every bar, every business, and every block goes all out.”
Celebrating Halloween in Hillcrest means more than just partying — it means stepping into a space where queerness is uplifted, honored, and unapologetically celebrated. Thousands of visitors from across San Diego and beyond flock to the neighborhood each year, turning it into a vibrant, open-air queer festival.
👻 A Ghostly Listener Story
No Halloween blog would be complete without a little spookiness, and Hot Air listeners always deliver. One listener, a gay man visiting Provincetown, shared a story that is both terrifying and hilarious — and yes, a little drag-inspired.
He was getting ready for a Halloween party in a full dragged-up Catwoman costume — vinyl bodysuit, smoky eyes, red lips, the whole nine yards. Music was playing, makeup was being perfected, and everything seemed normal… until the knocking started.
Soft, deliberate taps at the door. Every time he answered, the hallway was empty. Then his phone — sitting across the room — started playing It’s Raining Men, even though he hadn’t touched it.
The knocking continued, louder and more insistent. A makeup brush rolled off the vanity, seemingly on its own. And then, in the mirror, he saw it: a faint shimmering figure adjusting a wig behind him. A ghost, it seemed, eager to get into drag.
Terrified but fascinated, he fled to the lobby, only to learn that the room had belonged to a drag performer who had passed away on Halloween years prior. Every year, legend says, she still prepares for her performance — a ghostly, glamorous reminder that Halloween is not just spooky, but fabulously queer.
Stories like this remind us that Halloween is about more than candy or costumes. It’s about creativity, identity, and sometimes a little supernatural magic.
🎉 Nightmare on Normal Street: Hillcrest’s Legendary Block Party
No discussion of Halloween in Hillcrest is complete without Nightmare on Normal Street, San Diego’s largest LGBTQ+ Halloween celebration. This iconic event began in 1992 as a community gathering outside The Center and has grown into a full-blown block party attracting nearly 2,000 attendees every year.
In 2014, the Hillcrest Business Association (HBA) took over the event, providing the resources to expand it even further. Now, Nightmare on Normal Street is a cornerstone of Hillcrest’s identity, drawing visitors from all over the city to celebrate queer culture, creativity, and community.
🎶 What to Expect at Nightmare 2025
This year, Nightmare on Normal Street is happening on Friday, October 31st, from 5 PM to 11 PM, on University Avenue between Herbert and Centre Street, right in the heart of Hillcrest.
The event features:
Main Stage & DJs: Presented by Rich’s Nightclub, San Diego’s hottest DJs will keep the dance floor packed all night.
Runway Costume Contest: A fabulous drag queen hosts a high-energy runway contest with over $3,000 in prizes from local businesses.
Vendors & Local Flavor: Food, drinks, and artisan booths from Hillcrest favorites like Gioia’s Room Boutique.
Outdoor Cocktail Bar & Dance Floor: Dance under the stars with cocktails in hand and thousands of costumed friends around you.
Nightmare on Normal Street isn’t just a party — it’s an experience. Thousands of people in creative, colorful costumes come together to cheer each other on, celebrate visibility, and keep queer Halloween traditions alive.
🌟 Hillcrest Beyond the Block Party
While Nightmare anchors the celebration, Halloween takes over the entire neighborhood. After the block party, nightlife continues with drag shows, themed DJ sets, and events at venues like:
Rich’s Nightclub
Gossip Grill
Flicks
Number One Fifth
The Rail
Uptown Tavern
EQ
Visitors can plan an entire Halloween weekend around Hillcrest using fabuloushillcrest.com/halloween, ensuring they hit every drag show, dance floor, and spooky spot the neighborhood has to offer.
💖 Why It Matters: Community & Culture
Nightmare on Normal Street isn’t just about fun — it’s about community, history, and pride. Fabulous Hillcrest’s mission is to unite people through culture, art, music, and food, while strengthening the identity of Hillcrest as San Diego’s LGBTQ+ cultural district.
Events like Nightmare fuel the local economy, shine a spotlight on small businesses, and remind everyone that Hillcrest isn’t just a nightlife district — it’s a historical, resilient, and proud queer community.
🎁 Hillcrest Halloween Giveaway
And now — the fun part! Hot Air is giving away two tickets to Nightmare on Normal Street!
Here’s how to enter:
Follow @hotairpodcast and @fabuloushillcrest on Instagram.
Comment “Hillcrest Halloween” and tag your Halloween bestie.
Whether you’ve never been to Nightmare or you’re a seasoned veteran, this is your chance to be part of one of the most fabulous LGBTQ+ Halloween celebrations in the country.
👻 Final Thoughts
Halloween is more than candy, costumes, or even scares. For the LGBTQ+ community, it’s a night to live authentically, express creativity, and celebrate queer culture with joy, freedom, and a little bit of spooky flair.
From the underground drag balls of the past to the ghostly tales of Provincetown, and from Hillcrest’s vibrant block parties to the ongoing traditions that unite the community, Halloween remains a night where queer identity is not just accepted — it’s celebrated.
So whether you’re dressing up in drag, telling ghost stories, or dancing down University Avenue, remember: Halloween is ours, fabulous and free. And this year, you might just win your way into Hillcrest’s most legendary party.
Stay spooky. Stay queer. Stay fabulous.