This new podcast explores the magic and secret history of Fire Island

Podcaster and journalist Jess Rothschild has been going to Fire Island for well over a decade. A long-time New Yorker who grew up on Long Island, she started out venturing to the storied LGBTQ+ vacation destination in 2008 and quickly became enchanted by what she calls the magic of the place.

That enchantment with Fire Island’s two neighboring LGBTQ+-dominated villages, Cherry Grove and the Pines, grew into an obsession with the community’s unique dynamics and little-known history. Rothschild, the creator and host of the podcast Hot Takes & Deep Dives, channeled that obsession into an ambitious project delving into this one-of-a-kind gay haven: a new podcast docuseries, Finding Fire Island.

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The series, which features interviews with Margaret Cho, Joel Kim Booster, Matt Rodgers, and many others, premiered earlier this month, and will continue with episodes covering the island’s secret history, its contemporary hedonistic atmosphere, and the thorny issues around who does and does not feel welcome in what Rothschild describes as Fire Island’s “gay fantasia.” LGBTQ Nation recently chatted with Rothschild about Finding Fire Island, the magic of the Grove and the Pines, and the island’s place in LGBTQ+ culture and history.

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LGBTQ NATION: You cover gay culture and New York culture on your podcast Hot Takes & Deep Dives. Why does Fire Island deserve an entire podcast docuseries?

JESS ROTHSCHILD: I’ve always been obsessed with Fire Island, and I particularly started getting really obsessed with the history of Fire Island maybe five years ago. But there’s not a lot out there. You can’t even find [Crayton Robey’s 2003 documentary] When Ocean Meets Sky. It’s actually unavailable. So, you’ve got to search. You’ve got to dig. And two years ago, I did an episode of Hot Takes & Deep Dives with my friend Ben Rimalower—it’s the most unhinged, chaotic episode, but I was just like, “Can we just do an episode on Fire Island?” It was, like, manic, because we were both telling stories about our favorite experiences. I’m interviewing him while still trying to weave in the history, but it’s going off the rails.

That was one of the most fun episodes I ever did, and I got so much feedback about it. It was like, I just wished this thing existed. And I just saw it. I saw the vision, I saw the episode outlines.

I’ve also been going to Fire Island for years, and when I saw Fire Island—Joel Kim Booster’s movie—I felt like I was watching footage that someone had filmed in my home and released to the world without my permission. Now, that sense of ownership is obviously kind of absurd, but I do think that a lot of people who go to Fire Island every year feel that. You know, while people know about Fire Island, it hasn’t actually been depicted in a lot of mainstream media. So, did you receive any pushback from anyone who didn’t want to talk to you for the series, who didn’t want to kind of expose this secret garden to the wider world?

Nobody said no. The only person who I couldn’t get—and I’m pretty sure it’s because it was a message that just went into the ether—was Robin Byrd, who is an iconic figure. People were thrilled to tell all of their sex stories, which are all in the fourth episode. But also, the older folks, people who have been there since the 60s and the 70s, they were very happy to have the platform to tell their stories. I think the older generation is very happy to tell the history. They’re very much like, “The younger generation needs to know.”

Your podcast isn’t just a snapshot of what Fire Island is now, it’s also a deep dive into its history and how it became what it is today. What was the most fascinating thing you learned about that deeper history?

Probably that John Whyte, who was the owner of the Pines, the one who made it, who brought sophistication and celebrities—that’s why the Pines became elite. But I didn’t know that he was a closeted gay guy, and he was very conservative. So, I think that is very interesting, and we focus on that in the Pines episode.

Also, the Invasion of the Pines. I have two of the people who were on the first Invasion of the Pines boat, which was a little water taxi. Thousands of people go to the Invasion every July 4^th and they have no idea why this is happening. Why are thousands of people in drag on ferries doing this? And to hear the real story—it’s mainly this one guy, Pansy. He was like, “We were approaching the harbor and we thought, What if they kick us out? What if they stone us?” They were going into a closeted community in 1976. He really gets across that it was all fun and games on the water taxi, but as they got to the Pines harbor, they were like, “Oh my god!” It turns out, of course, that they were embraced and everybody cheered, but there’s suspense in that story. With all the Don’t Say Gay laws and drag being banned in Florida, it has never been more relevant.  

You’ve noted in press material about the podcast and on the show itself that “Finding Fire Island” is one of the few pieces of media about Fire Island from the perspective of a woman. How does your perspective impact the show and set it apart from other depictions of Fire Island?

The most well-known media about Fire Island—we’re talking about the most recent Fire Island movie. It’s all men and Margaret Cho in a small part. Longtime Companion: all men and Mary Louise Parker in a very small part. The Normal Heart, more recently American Horror Story shot on Fire Island. People think that it is a playground for men—and mostly white gay dudes. I feel very embraced in the Pines. Women tend to go to the Grove, and more trans people. And I think that hearing my voice, and also bringing a lot of other female voices onto the show—it is deliberate that every episode has at least three women in the episodes. I was so hyper-conscious of it not being once again overrun by men. Because that’s a stereotype. When you see the Fire Island movie, you don’t see women. And I think with this, hearing me and hearing the other women and trans women throughout the episodes, it really paints my Fire Island experience, which is very mixed. It’s very welcoming, very mixed, and I think my mission is that the more people who hear this, it dispels that stereotype. It’s going to encourage more and more women, trans people, people of color to come out, because you’re claiming that space. This is a space for us too.

I don’t know how strictly accurate this is, but I’ve often thought of Fire Island’s queer communities as something of a template for a queer separatist paradise. They’re some of the only places in the world where queer people are the majority. Meanwhile, you describe it as a “fantasy world.” I’m curious what you make of that tension between the sense that many queer people get in the Grove and the Pines of having found a place where they can exist away from, as one person described it, the “straight gaze,” and the fact that that is ultimately a fantasy, because most people can’t live there year-round.

I think it’s a microcosm for the rest of the world. All of the problems in the world—racism, sexism, politics—all of that plays out in these two tiny remote gay villages. And it can be a free for all. But when Black and brown people on the podcast talk, they talk about how you think it’s going to be a fantasy, and for them on their first visit, it can be a nightmare, and I dig deeper into that.

It’s not a fantasy. And that is my biggest takeaway. That’s a superficial look at it, and when you peel it back you see that this is a real place that has real homeowners and real things going on. Stuff has to get done—winterizing your house and all this other stuff that’s such a pain—and then you see how these politics play out.

I was also struck listening to the first two episodes by how frank so many people—particularly the younger gay boys—were about how much staying on Fire Island can take out of you. Like, they talk about the Bucket of Blood ferry on Monday mornings and feeling just exhausted and emotionally strung out after a weekend in the Pines. It’s like, the island demands its sacrifice or something.

Absolutely. There’s a lot going on and I think you feel the pressure, especially if you only have a couple days, you want to do it all. You want to go to every party, every pool party, everything, you want to wear all the outfits. It’s true, it can be exhausting.

However, there are also other people who opt out of all that. They just go to the beach. Sober people—in the episode where people are talking about all the sex and drugs, there’s a solid 10 minutes where I interview a lot of sober people. And by the way, all the people that are talking about all the sex and the drugs and the craziness, a lot of the people you’re hearing in the first two episodes, it’s revealed that they’re actually sober, and how they do it. Other people talk about how they go to their 12-step meetings on the beach every day because it just helps ground them.

The overall theme is that it’s a choose-your-own-adventure. You can make it whatever you want it to be.

Like so many gay havens, Fire Island is exclusive. People of color have not, historically, felt particularly welcomed. It’s also expensive and accommodations are limited, so you don’t just have to have money to stay there, you also either have to have a share house group to stay with or find a place to stay before they’re all booked. What do you think those barriers to entry say about Fire Island and similar gay destinations more broadly?

When you think about gay communities—Fire Island, Provincetown, Palm Springs, Key West, but particularly Fire Island and Provincetown—look at the map, where these two places are. They’re very remote. I guess the real question is: Why are all the gay places so remote?

Are we trying to get so far away from, like, normal heterosexist society that we make it hard for our entire community to join us?

I think it’s because when these places were established, they were secret getaways. Being gay was criminalized in the United States, so people found these undeveloped havens that were close to big cities. But I think that they were looking for a private getaway. The privacy was intentional because people weren’t out—especially celebrities. They were protective of their careers. The Broadway crowd, actors—Rock Hudson used to go out to the Pines all the time, and they couldn’t be out. It being underground and a secret thing, I think, was also part of the sexiness of it. These places were first heard of through word of mouth. That was the point—and that’s when they actually say it was the best.