An Insider's Guide To Montauk, From The Author Of This Summer's Hottest Beach Read

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The author's debut book, Out East, chronicles the first summer he spent in a share house in Montauk. The action takes place in the summer of 2013, when he was 27.

John Glynn

The West Coast may boast endless days of sunshine throughout the year, but there’s simply no competing with an East Coast summer. The mass weekend exodus of city-dwellers from Memorial through Labor Day is a time-honored tradition up and down the Mid-Atlantic—from Boston to New York to Washington DC.

Yet, no seaside destination is more popular at the moment than Montauk. Located on the easternmost point of Long Island, this formerly sleepy fisherman’s town has transformed into a summertime hotspot in recent years, one best described as ‘Manhattan on the rocks.’ So, how best to navigate these (occasionally crowded) shores at “The End of the World”?

Hailed as a “delicate and highly gifted writer” (Andre Aciman, Call Me By Your Name), Glynn's memoir of a debauched and wistful Long Island summer "revives the spirit of Fitzgerald’s The Great Gatsby to speak for our present moment" (Stefan Merrill Block, Oliver Loving). But, unlike Fitzgerald, who spent his summers along the North Shore, old sport, Glynn prefers his Long Island destinations to be a little more remote—the End of the World, to be exact.

Oleg March

For this insider’s guide to summer in Montauk, we consulted a veritable expert on the topic: John Glynn, debut author of Out East: Memoir of a Montauk Summer, released last month by Grand Central Publishing.  Glynn’s tale of first love and self-discovery unfolds over the course of a single summer in a Montauk share house, the author’s first. It’s in this invigorating and chaotic environment—amidst the parties and the hangovers and the dreaded Sunday morning train rides home on the LIRR—that the author realizes, for the first time in his life, that he’s falling in love with a man.

Glynn deftly captures the anxiety of modern dating—hyper-analyzing the minutia of our digital age, from texts to Gchats to group emails, to navigating relationships that, increasingly, are hazily defined. While the the peculiarity of his experience is rendered in immaculate detail, the object of his affection is painted in broader strokes. But, how well do we ever really know the person we fall in love with? Out East is a testament to falling in love with love itself, with the frightening prospect of finally being accepted for exactly who you are.

And herein lies the magic of the book—despite knowing (likely from past experience) that that first crushing love might not work out, you desperately root for him anyway. You cash in when you know you should be cashing out. And, like any proper love affair, you’re in despair when it’s all over.

The best surfing spots on Montauk are found at Ditch Plains, though social-minded vacationers may opt for the sand in front of Sloppy Tuna.

Oleg March

With its shared milieu of unrequited love and summertime debauchery on the coast of Long Island, Out East has been compared to a modern-day Great Gatsby. Yet, while Daisy Buchanan’s voice may have sounded like money, Matt’s sounded like hope, like belonging, like the feeling Glynn felt driving into Montauk on a Friday night:

“You can hang your hopes on Montauk, on the romance and glamour of a summer night. There’s a reason why The Affair is set in Montauk, why Ross and Rachel get back together on season 3 of Friends in Montauk, why Hannah Horvath has an affair in Montauk that propels the entire final season of Girls.”

For a new generation of dreamers and seekers, Montauk is the new East Egg. The string lights of the Surf Lodge beam across Fort Pond, promising parties you can’t get into, full of people you’re not cool enough to meet—not yet.

Oleg March

Out East is the latest addition to the cultural canon devoted to the endless summers and far-too-fleeting love affairs of Montauk, a storied town rightfully known as ‘the end of the world.’ An antidote to the wearying pace and grueling hours of New York City, it’s just past where the manicured lawns end, where the messiness and abandon of youth can be reclaimed.

It’s been six years since that fateful summer chronicled in Out East, but John Glynn still returns to the town year after year. We spoke to him about the best way to cut the line at Surf Lodge, and who to call when an available Uber is nowhere to be found. Read on for his insider’s guide to chasing an eternal summer in Montauk—even if you’re only visiting for the weekend

The iconic, and photogenic, Montauk Point Light, which also boasts an accompanying museum

Oleg March

Out East chronicles your very first summer spent in a Montauk share house. Was that the first time you’d ever visited Montauk?

John Glynn: I’d gone out to Montauk once or twice before that: Once right after college and once for a friend’s birthday. Both were just short weekend trips, and I really loved it out there. The landscape is really beautiful, the beaches are beautiful, fun nightlife.

How much do you think Montauk has changed since that summer you wrote about in your book, the summer of 2013?  

JG: It's changed a lot. I hesitate because I feel like I’m not particularly entitled to answer that, because I am a visitor. It was one of the conflicts that we felt all summer. We went into this experience wanting to treat the town with as much respect as possible. But, we would hear stories of people from other share houses, or other weekenders, doing all sorts of weird things.

We felt that, just by our sheer presence, just by being there, we were somehow complicit—were we contributing to that culture?  I think there's always going to be tension between a local community and vacationers, and it’s our responsibility to honor and respect the place that we call home on the weekends.

The beach at the Surf Lodge. The hotel is buzzing with activity both day and night, especially when a concert series is underway.

Oleg March

What do you think most differentiates Montauk from the rest of the Hamptons?

JG: When I was writing the book, I asked all the people I profiled in the house the same question: What is that feeling you feel when you cross into Montauk on a Friday night? Everyone I talked to brought up the same three words. It was amazing. They all said it represented freedom, it represented escape, and it represented family.

To me, Montauk really is a place for dreamers—more so than other areas in the Hamptons, or other beach communities in the tristate area. Partially because it's so geographically isolated: You have to go all the way out to the tip of Long Island, so there’s a journey involved. You feel like you're out there.

When you look back to the 1920s: Carl Fischer, the famous architect who built up Miami, came to Montauk and looked out at the landscape and was so inspired by it that he thought, This will be the Miami Beach of the north. He had a big vision, and started building these Tudor Revival structures (like White's pharmacy and Shagwong), which you can still see today in the center of Montauk.

But then there was a hurricane, and the depression, and the construction halted.  And Montauk was left in this half-formed state. Which felt like an apt symbol to us that summer because we were also, internally, in a half-formed state. Montauk is this fixed place in my mind, but it’s also in a constant state of becoming.

Montauk was once primarily known as a fisherman's paradise, as its remote location was once a deterrent for weekend visitors

Oleg March

Like New York City.

JG: Like New York City, exactly. And, just like New York, you can graft your dreams across it. You can hang your hopes on Montauk, on the romance and glamour of a summer night. There’s a reason why The Affair is set in Montauk. There’s a reason why, on season three of Friends, Ross and Rachel get back together  in Montauk, why Lena Dunham has an affair in Montauk that propels the entire final season of Girls.

Isn’t Eternal Sunshine of the Spotless Mind set in Montauk, too?

JA: Yes! Eternal Sunshine in Montauk in the off-season. Obviously I'm not the first person to feel this way about Montauk. I think it really represents that romance and mystery to a lot of people.

When do you think is the best season to visit Montauk?

JG: Most of my visits to Montauk have been limited from Memorial Day to Labor Day. I have visited during the off-season and the energy is very different. It’s much more tranquil and low-key going out in the winter or spring. I’ve gone out for the Saint Patrick’s Day and it’s a festive time to go out to Montauk. They have all these festivals in the fall, too—it’s definitely a year-round place. I’m only speaking from the perspective of an outsider who goes to visit, not a local. But, it’s just beautiful there in the summer.

The share house atmosphere depicted in 'Out East' portrays a summer camp-style environment of shared living for young adults

Oleg March

Do you think that Montauk’s mix of wildness and glamour is what makes it the ultimate New York getaway? I know you grew up in New England, and the beach scene in Cape Cod versus New York is very different.

JG: Yes, for sure. It’s the full spectrum. Montauk has its roots as a fisherman's town, and it maintains that vibe, but it’s also a big destination for surfers and all sorts of seekers and free spirits. But then, especially over the past few years, you also have that New York City vibe, too.

There's definitely a Manhattan footprint that is growing. Some people would say that’s to the detriment of Montauk, maybe a lot of people. There's a wild spirit to the nightlife here—an unbridled spirit about it—that I think is really appealing for a lot of people.

That unbridled spirit matches the landscape, too. It’s definitely wilder and less groomed.

JG: Absolutely. I never thought of it that way, but that’s really true.

What’s the best way to get to Montauk from New York?

JG: I am an avid train rider. I live and die by the LIRR. If you can get yourself a seat, then it’s easier to do work, and the time goes by faster. But if you’re looking for a more upscale way of traveling, there's the Ambassador Line bus, which can be nice. It’s a little cushier. I don’t know, you always hear stories about people who took Blades out to the Hamptons. Not my scene, and definitely prohibitively expensive. But driving can be the best way or the worst way, depending on traffic.

What are the best places to stay in Montauk?

JG: The Montauk Blue Hotel is right on the water and centrally located. My parents have stayed there. But if you’re looking for a place that also has a built-in nightlife, a built-in scene, then obviously the Surf Lodge is the hotspot, probably, of all of Montauk. It’s located on the pond and gets beautiful sunsets. Ruschmeyer's, too, is this former summer camp that was refashioned into a Dirty Dancing-style hotel and restaurant—it’s also really fun, especially on Friday nights.

The light in Montauk is particularly beautiful, one benefit from being situated at "The End" of Long Island

Oleg March

What is the typical Out East schedule for a summer weekend ? If someone wanted to spend a Saturday in Montauk the way you spend yours in the book, how would their day unfold?

JG: Okay, so you would wake up on a Saturday probably a little hungover, so you would desperately need an iced coffee and a breakfast sandwich. So you would probably go to Montauk Bake Shoppe in the center of town and get a bacon egg and cheese to your liking—maybe on a wrap, throw in some avocado. Then you would go to Left Hand and get an iced coffee there (they have delicious coffee), and there’s one located by the harbor, and another right in town.

So then, from there, you would peace together the night with your friends, swap war stories, and get your sunscreen on and head straight to the beach. Depending on the kind of vibe you were looking, you might set up camp near the Sloppy Tuna, so you could catch some rays, swim in the ocean, you’d bring a book probably, get lost in a good beach read.  And then you might head over to the Sloppy Tuna around 3 or 4 for a transfusion—and from there we would always go to Cyril's, but Cyril's is no longer.

Depending on the day of the week, you might head over to Surf Lodge if there’s an early concert. They have some amazing acts that will come to play in the early evening and those concerts are free. It’s just that the hardest part is getting in—that can be tricky.

Do you have any tips for getting in?

JG: Friendliness and kindness goes a long way. Being argumentative will just keep you shut out. Or, call ahead and make a dinner reservation—that’s one way to be sure you’ll get in. Or, if you’re willing to pony up a lot of money, you can probably buy a table. But that’s a route that I’ve never been able to go myself.

The prevailing aesthetic of visitors to Montauk is decidedly hipster, hence the birth of the no-fedora logo in local establishments, frustrated with the influx of tourists

Oleg March

Where should you go to heal a hangover  in Montauk?

JG: If you’re looking for hair of the dog, I like going to Lynn’s Hula Hut. They have a huge cocktail menu and it’s a very soothing, tranquil environment—sort of a tiki bar situation. Also, Goldberg’s is a total hangover rescue. Go there for bagels.

Best places to eat?

JG: Harvest, lobster at Duryea’s, seafood from the Inlet, Salivar’s, chicken quesadillas from The Point. But The Dock is my favorite. For drinks: The Ruschmeyer (a watermelon drink from Ruschmeyer's that's so good), the Endless Summer from Surf Lodge, and a cold Bud Light and a titanium bottle from the Memory Motel.

Best date spot?

JG: Who goes on dates in Montauk? I guess if I had to choose, though, I’d maybe say ENE (East by Northeast).

Much like in college, the characters of 'Out East' regularly flock to the same handful of bars every night; a tactic that also ensures better chances for running into someone you're hoping to see

Oleg March

Most underrated spots in Montauk?

JG: Well, The Point and the Memory Motel aren’t underrated, but they truly are the most fun, if you hit them with a group.

Is anything underrated in Montauk anymore?

JG: Truly. Nothing is underrated in Montauk now.

What would you say to someone who wakes up in someone else’s share house? What’s the best way to escape in the morning?

JG: Call Montauk's Best Taxi and ask for Henry.

Is there Uber in Montauk?

JG: There is now. But no one will get there faster than Henry.

 

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The author's debut book, Out East, chronicles the first summer he spent in a share house in Montauk. The action takes place in the summer of 2013, when he was 27.

John Glynn

The West Coast may boast endless days of sunshine throughout the year, but there’s simply no competing with an East Coast summer. The mass weekend exodus of city-dwellers from Memorial through Labor Day is a time-honored tradition up and down the Mid-Atlantic—from Boston to New York to Washington DC.

Yet, no seaside destination is more popular at the moment than Montauk. Located on the easternmost point of Long Island, this formerly sleepy fisherman’s town has transformed into a summertime hotspot in recent years, one best described as ‘Manhattan on the rocks.’ So, how best to navigate these (occasionally crowded) shores at “The End of the World”?

Hailed as a “delicate and highly gifted writer” (Andre Aciman, Call Me By Your Name), Glynn's memoir of a debauched and wistful Long Island summer "revives the spirit of Fitzgerald’s The Great Gatsby to speak for our present moment" (Stefan Merrill Block, Oliver Loving). But, unlike Fitzgerald, who spent his summers along the North Shore, old sport, Glynn prefers his Long Island destinations to be a little more remote—the End of the World, to be exact.

Oleg March

For this insider’s guide to summer in Montauk, we consulted a veritable expert on the topic: John Glynn, debut author of Out East: Memoir of a Montauk Summer, released last month by Grand Central Publishing.  Glynn’s tale of first love and self-discovery unfolds over the course of a single summer in a Montauk share house, the author’s first. It’s in this invigorating and chaotic environment—amidst the parties and the hangovers and the dreaded Sunday morning train rides home on the LIRR—that the author realizes, for the first time in his life, that he’s falling in love with a man.

Glynn deftly captures the anxiety of modern dating—hyper-analyzing the minutia of our digital age, from texts to Gchats to group emails, to navigating relationships that, increasingly, are hazily defined. While the the peculiarity of his experience is rendered in immaculate detail, the object of his affection is painted in broader strokes. But, how well do we ever really know the person we fall in love with? Out East is a testament to falling in love with love itself, with the frightening prospect of finally being accepted for exactly who you are.

And herein lies the magic of the book—despite knowing (likely from past experience) that that first crushing love might not work out, you desperately root for him anyway. You cash in when you know you should be cashing out. And, like any proper love affair, you’re in despair when it’s all over.

The best surfing spots on Montauk are found at Ditch Plains, though social-minded vacationers may opt for the sand in front of Sloppy Tuna.

Oleg March

With its shared milieu of unrequited love and summertime debauchery on the coast of Long Island, Out East has been compared to a modern-day Great Gatsby. Yet, while Daisy Buchanan’s voice may have sounded like money, Matt’s sounded like hope, like belonging, like the feeling Glynn felt driving into Montauk on a Friday night:

“You can hang your hopes on Montauk, on the romance and glamour of a summer night. There’s a reason why The Affair is set in Montauk, why Ross and Rachel get back together on season 3 of Friends in Montauk, why Hannah Horvath has an affair in Montauk that propels the entire final season of Girls.”

For a new generation of dreamers and seekers, Montauk is the new East Egg. The string lights of the Surf Lodge beam across Fort Pond, promising parties you can’t get into, full of people you’re not cool enough to meet—not yet.

Oleg March

Out East is the latest addition to the cultural canon devoted to the endless summers and far-too-fleeting love affairs of Montauk, a storied town rightfully known as ‘the end of the world.’ An antidote to the wearying pace and grueling hours of New York City, it’s just past where the manicured lawns end, where the messiness and abandon of youth can be reclaimed.

It’s been six years since that fateful summer chronicled in Out East, but John Glynn still returns to the town year after year. We spoke to him about the best way to cut the line at Surf Lodge, and who to call when an available Uber is nowhere to be found. Read on for his insider’s guide to chasing an eternal summer in Montauk—even if you’re only visiting for the weekend

The iconic, and photogenic, Montauk Point Light, which also boasts an accompanying museum

Oleg March

Out East chronicles your very first summer spent in a Montauk share house. Was that the first time you’d ever visited Montauk?

John Glynn: I’d gone out to Montauk once or twice before that: Once right after college and once for a friend’s birthday. Both were just short weekend trips, and I really loved it out there. The landscape is really beautiful, the beaches are beautiful, fun nightlife.

How much do you think Montauk has changed since that summer you wrote about in your book, the summer of 2013?  

JG: It's changed a lot. I hesitate because I feel like I’m not particularly entitled to answer that, because I am a visitor. It was one of the conflicts that we felt all summer. We went into this experience wanting to treat the town with as much respect as possible. But, we would hear stories of people from other share houses, or other weekenders, doing all sorts of weird things.

We felt that, just by our sheer presence, just by being there, we were somehow complicit—were we contributing to that culture?  I think there's always going to be tension between a local community and vacationers, and it’s our responsibility to honor and respect the place that we call home on the weekends.

The beach at the Surf Lodge. The hotel is buzzing with activity both day and night, especially when a concert series is underway.

Oleg March

What do you think most differentiates Montauk from the rest of the Hamptons?

JG: When I was writing the book, I asked all the people I profiled in the house the same question: What is that feeling you feel when you cross into Montauk on a Friday night? Everyone I talked to brought up the same three words. It was amazing. They all said it represented freedom, it represented escape, and it represented family.

To me, Montauk really is a place for dreamers—more so than other areas in the Hamptons, or other beach communities in the tristate area. Partially because it's so geographically isolated: You have to go all the way out to the tip of Long Island, so there’s a journey involved. You feel like you're out there.

When you look back to the 1920s: Carl Fischer, the famous architect who built up Miami, came to Montauk and looked out at the landscape and was so inspired by it that he thought, This will be the Miami Beach of the north. He had a big vision, and started building these Tudor Revival structures (like White's pharmacy and Shagwong), which you can still see today in the center of Montauk.

But then there was a hurricane, and the depression, and the construction halted.  And Montauk was left in this half-formed state. Which felt like an apt symbol to us that summer because we were also, internally, in a half-formed state. Montauk is this fixed place in my mind, but it’s also in a constant state of becoming.

Montauk was once primarily known as a fisherman's paradise, as its remote location was once a deterrent for weekend visitors

Oleg March

Like New York City.

JG: Like New York City, exactly. And, just like New York, you can graft your dreams across it. You can hang your hopes on Montauk, on the romance and glamour of a summer night. There’s a reason why The Affair is set in Montauk. There’s a reason why, on season three of Friends, Ross and Rachel get back together  in Montauk, why Lena Dunham has an affair in Montauk that propels the entire final season of Girls.

Isn’t Eternal Sunshine of the Spotless Mind set in Montauk, too?

JA: Yes! Eternal Sunshine in Montauk in the off-season. Obviously I'm not the first person to feel this way about Montauk. I think it really represents that romance and mystery to a lot of people.

When do you think is the best season to visit Montauk?

JG: Most of my visits to Montauk have been limited from Memorial Day to Labor Day. I have visited during the off-season and the energy is very different. It’s much more tranquil and low-key going out in the winter or spring. I’ve gone out for the Saint Patrick’s Day and it’s a festive time to go out to Montauk. They have all these festivals in the fall, too—it’s definitely a year-round place. I’m only speaking from the perspective of an outsider who goes to visit, not a local. But, it’s just beautiful there in the summer.

The share house atmosphere depicted in 'Out East' portrays a summer camp-style environment of shared living for young adults

Oleg March

Do you think that Montauk’s mix of wildness and glamour is what makes it the ultimate New York getaway? I know you grew up in New England, and the beach scene in Cape Cod versus New York is very different.

JG: Yes, for sure. It’s the full spectrum. Montauk has its roots as a fisherman's town, and it maintains that vibe, but it’s also a big destination for surfers and all sorts of seekers and free spirits. But then, especially over the past few years, you also have that New York City vibe, too.

There's definitely a Manhattan footprint that is growing. Some people would say that’s to the detriment of Montauk, maybe a lot of people. There's a wild spirit to the nightlife here—an unbridled spirit about it—that I think is really appealing for a lot of people.

That unbridled spirit matches the landscape, too. It’s definitely wilder and less groomed.

JG: Absolutely. I never thought of it that way, but that’s really true.

What’s the best way to get to Montauk from New York?

JG: I am an avid train rider. I live and die by the LIRR. If you can get yourself a seat, then it’s easier to do work, and the time goes by faster. But if you’re looking for a more upscale way of traveling, there's the Ambassador Line bus, which can be nice. It’s a little cushier. I don’t know, you always hear stories about people who took Blades out to the Hamptons. Not my scene, and definitely prohibitively expensive. But driving can be the best way or the worst way, depending on traffic.

What are the best places to stay in Montauk?

JG: The Montauk Blue Hotel is right on the water and centrally located. My parents have stayed there. But if you’re looking for a place that also has a built-in nightlife, a built-in scene, then obviously the Surf Lodge is the hotspot, probably, of all of Montauk. It’s located on the pond and gets beautiful sunsets. Ruschmeyer's, too, is this former summer camp that was refashioned into a Dirty Dancing-style hotel and restaurant—it’s also really fun, especially on Friday nights.

The light in Montauk is particularly beautiful, one benefit from being situated at "The End" of Long Island

Oleg March

What is the typical Out East schedule for a summer weekend ? If someone wanted to spend a Saturday in Montauk the way you spend yours in the book, how would their day unfold?

JG: Okay, so you would wake up on a Saturday probably a little hungover, so you would desperately need an iced coffee and a breakfast sandwich. So you would probably go to Montauk Bake Shoppe in the center of town and get a bacon egg and cheese to your liking—maybe on a wrap, throw in some avocado. Then you would go to Left Hand and get an iced coffee there (they have delicious coffee), and there’s one located by the harbor, and another right in town.

So then, from there, you would peace together the night with your friends, swap war stories, and get your sunscreen on and head straight to the beach. Depending on the kind of vibe you were looking, you might set up camp near the Sloppy Tuna, so you could catch some rays, swim in the ocean, you’d bring a book probably, get lost in a good beach read.  And then you might head over to the Sloppy Tuna around 3 or 4 for a transfusion—and from there we would always go to Cyril's, but Cyril's is no longer.

Depending on the day of the week, you might head over to Surf Lodge if there’s an early concert. They have some amazing acts that will come to play in the early evening and those concerts are free. It’s just that the hardest part is getting in—that can be tricky.

Do you have any tips for getting in?

JG: Friendliness and kindness goes a long way. Being argumentative will just keep you shut out. Or, call ahead and make a dinner reservation—that’s one way to be sure you’ll get in. Or, if you’re willing to pony up a lot of money, you can probably buy a table. But that’s a route that I’ve never been able to go myself.

The prevailing aesthetic of visitors to Montauk is decidedly hipster, hence the birth of the no-fedora logo in local establishments, frustrated with the influx of tourists

Oleg March

Where should you go to heal a hangover  in Montauk?

JG: If you’re looking for hair of the dog, I like going to Lynn’s Hula Hut. They have a huge cocktail menu and it’s a very soothing, tranquil environment—sort of a tiki bar situation. Also, Goldberg’s is a total hangover rescue. Go there for bagels.

Best places to eat?

JG: Harvest, lobster at Duryea’s, seafood from the Inlet, Salivar’s, chicken quesadillas from The Point. But The Dock is my favorite. For drinks: The Ruschmeyer (a watermelon drink from Ruschmeyer's that's so good), the Endless Summer from Surf Lodge, and a cold Bud Light and a titanium bottle from the Memory Motel.

Best date spot?

JG: Who goes on dates in Montauk? I guess if I had to choose, though, I’d maybe say ENE (East by Northeast).

Much like in college, the characters of 'Out East' regularly flock to the same handful of bars every night; a tactic that also ensures better chances for running into someone you're hoping to see

Oleg March

Most underrated spots in Montauk?

JG: Well, The Point and the Memory Motel aren’t underrated, but they truly are the most fun, if you hit them with a group.

Is anything underrated in Montauk anymore?

JG: Truly. Nothing is underrated in Montauk now.

What would you say to someone who wakes up in someone else’s share house? What’s the best way to escape in the morning?

JG: Call Montauk's Best Taxi and ask for Henry.

Is there Uber in Montauk?

JG: There is now. But no one will get there faster than Henry.

 

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I am a New York-based writer with an incurable case of wanderlust. I blame my parents—they took me to the Arctic Circle when I was only 14 months old. I’ve since visited...