Montauk to me, is a place of contrast and extremes. I associate it with late nights, but also early mornings. Relaxation, but going hard (sometimes way too hard). Lazy summer log days, and also some of the biggest, coldest, heaviest surf I’ve ridden on the east coast. There is mysterious and natural beauty, but also a strange cosmopolitan scene due to it’s proximity to NYC, and a casual allure that seems to attract a wealthy & trendy crowd. It’s a playground where there are no rules in many ways though. Since I don’t live on the east coast anymore and my visits are usually brief, I mostly return in the fall and have some go-to spots that I need to hit up whenever in town. It’s hard for me to pick favorites when it comes to Montauk and this list has changed over the years with all the changes to the area, but here are the places that usually make me miss “The End” the most while I’m out west. Take em or leave em.
Montauk to me, is a place of contrast and extremes. I associate it with late nights, but also early mornings. Relaxation, but going hard (sometimes way too hard). Lazy summer log days, and also some of the biggest, coldest, heaviest surf I’ve ridden on the east coast. There is mysterious and natural beauty, but also a strange cosmopolitan scene due to it’s proximity to NYC, and a casual allure that seems to attract a wealthy & trendy crowd.
It’s a playground where there are no rules in many ways though. Since I don’t live on the east coast anymore and my visits are usually brief, I mostly return in the fall and have some go-to spots that I need to hit up whenever in town. It’s hard for me to pick favorites when it comes to Montauk and this list has changed over the years with all the changes to the area, but here are the places that usually make me miss “The End” the most while I’m out west. Take em or leave em.
Go Fishing: You’re on the eastern-most tip of Long Island, surrounded by water. Montauk is a fishing town first and foremost, so when in Rome. Book an early morning on the “Oh Brother”, Captain Rob knows what’s up. You’re pretty likely to catch the legal limit of stripers in the first hour you’re out. (Don’t quote me on that though – it’s still called “fishing” not “catching.”)
Surfing: It’s no secret that Montauk has waves, but my friends who live there might get butt-hurt if I give away the best kept secret on the east coast. Screw it – Ditch Plains is the spot, I surf there every time I’m in town and there only. Sssshhhh!
Spa Day At Gurney’s: Ocean water pool dips, steam, sauna, repeat.
Wedding Crashing At The Yacht Club: This place is a wedding factory, it’s pretty easy to just slip right into the wedding party scene on any given Saturday night during peak season. Just try to keep your shirt on and you should be fine.
Take A Hike: Amsterdam Beach trail, Shadmoor State Park, Hither Hills. There are some absolutely beautiful hiking trails in Montauk. Some of them feel like you are on the west coast, but without all the “no worries”.
Air & Speed: This is your go-to surf shop in town. Family owned and operated by the Foley clan, great vibes.
Pilgrim Surf + Supply: Although technically in Amagansett, this is just one of those shops with style that we love. Their unique aesthetic is on point.
Joni’s: has the best smoothies. And sandwiches. And cookies. And snacks. And everything.
Ditch Witch: is basically a food truck on the beach (that was there long before the food truck craze), it’s also the unofficial cultural and gossip hub of Montauk in the summer.
Naturally Good Foods: has good foods, naturally. Best health food store in town.
West Lake Fish House: If you want something a little more low key and sit down. Have lunch on the water, they have a killer fish sandwich and the best sushi around in my opinion. If you miss the old place (equally as good), it has moved to Salivar’s Dock.
St. Peter’s Catch: They will literally kill a lobster on the spot and make you the freshest lobster roll you’ve ever had in your life, truly made to order. One time I was waiting for my lobster roll before catching a train back to the city, I didn’t know why it was taking so long and I was about to miss my train. The owner apologized for the wait and drove me to the train station himself, freshly prepared lobster roll in hand. That is what Montauk is all about to me.
Luigi’s: As an Italian living in SoCal, I really miss some good ol’ Sicilian style dishes. This deli in East Hampton is the real deal. Pick some up on your way to or from The End.
Crows Nest: Again, lots of contrast here: casual but fancy, simple but gourmet, low key but a very cool scene. Whatever though, it’s a new Montauk staple in my mind. Besides being one of my favorite restaurants, the Inn here is also my new favorite place to stay in town. Sean MacPherson has perfected the art of subtle, casual, low key luxury in my opinion and this place is a prime example. His right hand gal Celine runs the joint, buy her a drink if you see her out and she might be able to cut your wait for a table short by an hour (maybe).
Inlet Seafood: is my old faithful. East end comfort food at it’s finest, and the freshest seafood available. Watch all the fishing boats come and go from the dining room view.
The Dock: If I could eat and drink beers at one place every night, this would be it. No cell phones please.
Shagwong: One of the few classic, old school establishments left in town. Bring your own fresh catch and they will prepare it however you like. Drink at the bar with local old salts any given night.
Harvest: Ridiculous off season specials.
Montauket: One of the best places to watch a sunset – not just in Montauk, but ever. They make a great Corona with lime too.
Memory Motel: See live music and get weird, very weird… I actually stayed here one night during a hurricane, they were the only place in town with power on a Saturday night. Things got weird. Embrace the weird. Ask for Artie.
Ruschmeyers: Dance all night with a very favorable gender ratio, then get creepy in the teepee.
The Surf Lodge: is a pretty rad, well-designed space that has become the go-to party scene in Montauk these days. It’s pretty cool if you ever make it past the mile long line out front to get in, then can actually make it to the bar to get a $20 drink. In case you are wondering, this is where all the beautiful people are. It’s also when you realize that for better or worse, you’re still only a quick train ride from NYC.
Liars: Blackout on mudslides and Budweisers. Nuff said. Seriously don’t ever talk about it again, ever.
Montauk Brewing Company: I’m just happy that with all the other new stuff popping up in Montauk, one of them is a local brewery – and a damn good one at that. If there’s one thing Montauk needs, it’s more beer.
Montauk Juice Factory: Drink all night, cleanse all day, right? I admit it; I love cold pressed juice and I’m happy to pay for it. (Yes, I do live in Venice Beach now.)
I should also not have a “where to drink” section without mentioning The Point and Sloppy Tuna. Both are perfect places to watch a game and possibly get punched in the face for doing something stupid.
On a side note, there are also a few things I miss dearly about Montauk. First being the East Deck, which was my favorite place to stay right on the beach (but didn’t cost beach front rates). A far second being Ronjo (my backup for when East Deck was booked and I couldn’t crash with friends), it’s just not the same seeing that rad statue painted gold. I will also miss the cosmic feeling and anticipation that I might casually end up at Peter Beard’s house for some weird reason and catch a glimpse into his fabled world (or just stumble on an epic party he was known to host). And of course, everyone’s favorite rowdy bar: Oyster Pond. Alas, I now accept that nothing gold can stay and those days are over. RIP.
That said, Montauk still is – and will always be a truly special and unique place. “This is the end, beautiful friend, the end.”
For more East End recos, check out the full article we did for the first issue of Whalebone Magazine on shelves all over New York now – or check out their recently launched website here:
/ All Photography & Words by Matt Titone
A goofy-footed graphic designer who hails from the first state, Delaware. After attending Flagler College in St. Augustine, FL then graduating from SCAD in Savannah, GA with a BFA in Graphic Design and Illustration, Matt moved to NYC and found work as a freelance designer and art director. In 2006 he moved west to Venice, CA where he co-founded ITAL/C Studio and now resides a bit further north in Oxnard.
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