The Ultimate Guide To Chilling In Montauk

You might not be able to judge a book by its cover, but you can certainly judge a Hamptonite by their town.

Despite its recently rowdy reputation, Montauk is, at its core, an out-of-the-way haven for surfers, fishermen and beach bums concerned less with chasing the scene and more with chasing sunny days and chill vibes.

Curious which casual spots are the top ones worth visiting next time you're all the way out East?

HERB'S MARKET
778 Montauk Highway
While you can pick up many a thing at Herb's, it's their fried chicken that's kept them a Montauk mainstay since opening up shop back in the 1940s. My family also swears by and hoards their coffee, so feel free to do with that what you will. 

DITCH WITCH
Ditch Plains Beach
Life in Montauk is all about the beach. From toes-in-the-sand mornings to late-into-the-afternoon surf sessions, Ditch Witch is the premier watering hole for locals. Salads, wraps, poke bowls, this beachside parking lot trailer serves up the best lunch in town. Oh, and don't forget about their famous sesame noodles!

HIDEAWAY
364 West Lake Drive
Quite literally hidden away, behind Cove Marina's parking lot of boats, perched above the dock, is Hideaway - a Mexican restaurant with zero frills. Come for the creamy corn, tacos and margaritas, stay for the feeling that life beyond that parking lot is somehow on pause.

SHAGWONG
774 Montauk Highway
This old school tavern has been around since 1936, and served everyone from The Rolling Stones to Andy Warhol. Ownership has passed hands over the years, but the crazy uncomfortable wood booths and sticky floors have stayed the same. It's a vibe.

CROW'S NEST
4 Old West Lake Drive
Few things in life are worth waiting in line for. Dinner at Crow's Nest is one of those things. The most desired spot out East might not take reservations, but there's plenty to keep you entertained while waiting for your table (which, admittedly, might take a minute, or ninety). Grab drinks and catch a waterfront sunset down at the Beach Bar. Shop at the Lingua Franca boutique - more on that in a minute. Huddle round the fire pit. Roll your kids down the hill. Really, there's loads to do. And if you're looking for a place to stay, definitely check out their cottages.

LINGUA FRANCA
4 Old West Lake Drive
A boutique that's only open at night? Intrigued much? Luxury fashion brand Lingua Franca has the most magical store out East. Shop their one-of-a-kind sweaters hand-embroidered with sayings like "Meet me in Montauk" and "The End," their easy-chic collection of ready-to-wear, and other carefully chosen treasures and summer styles from brands like Batsheva, Edie Parker, SuperSmalls and more.

HARVEST ON FORT POND
11 South Emery Street
Harvest on Fort Pond is Montauk fancy, which means it's really not fancy at all. Resist the urge to fill up on bread because the portions here are nuts. Like, prepare yourself for the most American sized helpings that would have a European straight up shook. The pasta's great, the pizza's great, the calamari salad is exactly what you want it to be - you'll be happy here.

GOSMAN'S
500 West Lake Drive
Gosman's is a slightly more affordable, far less sceney Duryea's. You're seated right on the inlet, a busy thoroughfare of boats passing by to amuse you. 

CAMP HERO
1898 Montauk Highway
Whether you're a nature enthusiast or a conspiracy theorist, Camp Hero State Park is worth a hike. The Bluffs at Turtle Cove are a must-see. And don't leave until you've poked around the creepy old abandoned military buildings marked with 'No Trespassing' signs. They're definitely more of a suggestion than a directive.

HERO BEACH CLUB
626 Montauk Highway
Aside from the giant winking smiley face painted on its side, Hero Beach Club is a pretty unassuming hotel. One of the first buildings to welcome you into town, it's a two second stroll to get your feet in the sand. As a guest, their staff will set you up with a plush lounger and sun umbrella. Not feeling the salt water? They've got a very lovely private pool to splash around in as well. 

MONTAUK BREWING COMPANY
62 South Erie Avenue
Montauk Summer Ale is the unofficial drink of town. Seriously, these cans are everywhere and every restaurant has it on tap. Hit up their brewery one afternoon to sample their pilsner, IPAs, hard seltzers and more. Oh, and scam on guys. This is totally the place to scam on guys.

SALIVAR'S
470 West Lake Drive
Eating on the dock is the best. Who doesn't want a front row seat as boats pull back into their slips from a day of fishing, offloading their catch?

LYNN'S HULA HUT
426 West Lake Drive
The name of this place alone is enough to make you happy, no? And the fact that their website is a .net tells you everything you need to know about the level at which they're operating. Housed in an old office trailer, this bamboo-lined tiki bar is an unpretentious scene. Just watch out for that Hula Juice, it'll get you!

JOHN'S PANCAKE HOUSE
721 Montauk Highway
How a town that's like five inches long has two pancake houses staring across the street at each other is beyond me. Still, John's Pancake House is a blast from the past in the most delightful way. They don't even have a website!

NATURALLY GOOD
779 Montauk Highway
Way ahead of the game, Naturally Good has been whipping up healthy, organic dishes since 1985. Stop by to pick up one of their killer smoothies, vegetable-packed salads and clean sandwiches. The Emma's Hummus Wrap is a big local favorite.

CYNTHIA ROWLEY
696 Montauk Highway
Cynthia Rowley's boutique has been a Montauk shopping staple for over 13 years. Stop in to check out the designer's latest collection of prête-à-party looks, eye-catching wetsuits and print-happy swim sets. Rowley's a summer local with a house over by the beach, so expect to run into her perusing the racks.

DURYEA'S
65 Tuthill Road
The ridiculousness of a $97 Lobster Cobb Salad aside, Duryea's is a most pleasant place to spend an afternoon or evening. Might we suggest the baked clams?

SUNSET BEACH
West Lake Drive
Montauk's got beaches all over the place - Ditch Plains, Gin Beach, Fort Pond, Kirk Park, Hither Hills, you get the point - but Sunset Beach is a special little sliver of sand. Just across the way from Gosman's, every day around sunset it floods with locals carrying chairs and blankets and, in the case of my family, boxes of pizza, all ready to dig in and watch the sky turn pink.

QUINCY MTK
28 South Etna Avenue
Local surfing celeb Quincy Davis set up shop in town a few years back, bringing her laid back style to the masses. She's got loads of fun fashion pieces to pick through, plus, obviously, a killer collection of swimwear.

LIAR'S
408 West Lake Drive
For a hot second there it looked like Liar's was a goner, but thanks to local couple Hali Devlin and Phil Baigent, the mudslides are still flowing! Under its new ownership this place is now technically Marlena’s Pack Out, but no one will actually call it that. Especially since nothing about it has changed. Not the barstools, not the menu, not even the bartenders. Spend your Saturday drinking impressively cheap beer and chatting up fishermen at this salty dive bar and you can thank me later.

JOHN'S DRIVE-IN
677 Montauk Highway
Cup or cone? Homemade ice cream, burgers, fries and milkshakes. What more could you possibly want?

WESTLAKE MARINA
352 Westlake Drive
Love swimming in the ocean? Probably don't take a stroll around the dock at Westlake Marina. The Thresher Sharks and Makos that you'll find hanging here certainly won't make you feel great. But still, there's no more interesting a way to spend your time in Montauk than chatting up charter boats as they weigh their spoils. Get in on the fishing action yourself and book a half-day on the water. I would personally recommend hopping aboard with Captain Skip on The Adios.

INLET SEAFOOD
541 East Lake Drive
Owned by six local fisherman, this is the premier place for seafood out East. Seriously, as the boat's pulling up the chef's getting . Also, with panoramic views of Block Island Sound, it's the best restaurant to catch the sunset.

FUDGE N STUFF
41 Carl Fisher Plaza
Who doesn't want fudge on a hot day? The existence of this store in a summer town has blown my mind my whole life. It sounds counterintuitive, but hey - their fudge is solid!

JONI'S
28 South Etna Avenue
Joni's is the place to grab breakfast in town. The egg wraps are well worth waking up early or biting the bullet and standing in line at 10AM for.

SURF LODGE
183 Edgemere Street
Avoid the crowds and grab an early weekday evening drink at Surf Lodge out on their beach.

[Photos via Herb's Market, Crow's Nest, Hero Beach Club, Duryea's, Inlet Seafood]