Dree Harper's So-Stylish Guide To Weekending In Montauk

Now, we have no objection to sitting on the beach all day and doing absolutely nothing on our precious weekend. But sometimes, when you're jetting off to Montauk (and especially if you're visiting the R29 Beach House), you get a hankerin' to explore local sights. And since this particular Long Island haven is practically terraformed to cater to NYC escape artists, there's no better place to enjoy some local flavor between beach reads. Resident Pinterest pro (not to mention vintage-shopper extraordinaire) Dree Harper clued us in on her favorite haunts in Montauk, and rest assured, you can find us taking the full tour of her list next weekend!
1 of 10
The Ditch Witch

"I felt like a cool local, eating at the Ditch Witch on Ditch Plains beach in Montauk. It's somewhat of a legend, this simple food truck, having been there for over 30 years. They have all the essentials to keep surfers, tourists, and hungry locals happily fed, like yummy breakfast burritos, cheese quesadillas, and delicious noodle salads. I had an iced coffee to perk me up a bit (it was yummy!), because the serenity of the ocean was doing its number on me. A definite must-stop if you're wanting simple and satisfying food on the beach while taking in the beauty of Ditch Plains."
DITCH WITCH TRUCK, MONTAUK.
PHOTO: COURTESY OF THE FOOD LIFE.
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2 of 10
Hither Hills Biking Trails

"Imagine hundreds of acres of woodland trails combined with miles of uninterrupted white, sandy beaches...sounds heavenly, doesn't it? Well, it is. And thanks to our friends at Montauk Bike Shop, my husband and I got our mountain-biking groove on and found the perfect trails to enjoy an afternoon riding. There are some special places in the United States that really floor me and speak God's country, and Hither Hills State Park is just that. I'm seriously dreaming of the next time we can make our way out there again!"
HITHER HILLS STATE PARK, 164 OLD MONTAUK HWY; 631-668-2554, MONTAUK.
PHOTO: COURTESY OF NYS PARKS, RECREATION AND HISTORIC PRESERVATION.
3 of 10
Cynthia Rowley

"I love that Cynthia Rowley set up shop in Montauk. It's such a cute boutique with a laid-back, surf-shack vibe. Colorful dresses and prints are everywhere, and the energy is definitely sunny. I think she is ahead of the curve as far as having a semipermanent pop-up shop like this in Montauk. I have a feeling other designers will follow in her footsteps, although I'm sure the locals are happy with just Cynthia. She's a Montauk girl, through and through, and stopping by her shop made the entire trip that much more memorable."
CYNTHIA ROWLEY, 696 MONTAUK HWY; 631-668-8077, MONTAUK.
4 of 10
The Crow's Nest

"I can't say enough about The Crow's Nest. My husband and [I] started our date night on the water, which is simply a grassy-hill stroll away from the restaurant. They actually have covered wooden chairs and tables in the water, where you can sip a nice glass of prosecco while watching the sail boats lazily drift by. Later that evening, as the strung lights and fire pit created a romantic glow, we made our way to the restaurant where we had fresh and beautiful food. Try the squash blossoms as an appetizer if they have them! So good! And apparently, it's the place to be seen in the fashion world, because I had a hard time concentrating on my food with all the gorgeous people floating around. It made such a great impression on us, we took [Refinery29] EIC Christene Barberich and her husband, Kevin, there the next night. It was just as fabulous!"
THE CROW'S NEST INN & RESTAURANT, 4 OLD WEST LAKE DRIVE; 631-668-2077, MONTAUK.
PHOTO: COURTESY OF THE CROW'S NEST INN & RESTAURANT.
5 of 10
Whoa Nellie Retro

"I love shops that hone in on the retro-Americana vibe like Whoa Nellie's does. It's a small space jam-packed with so much fun stuff from the archives of American culture, including funny tin signs, Nancy Drew and Hardy Boys books, throwback candy, as well as vintage jewelry and one-of-a-kind artisan pieces from all over the country. The shop has a contagious sense of humor, and it's impossible to leave without buying something, simply because you want a memoir of your time in one of Montauk's most popular shops."
WHOA NELLIE RETRO, 770 MONTAUK HWY; 631-668-2626, MONTAUK.
6 of 10
Coffee Tauk

"I'm from Seattle...we're born with coffee in our veins, so a good coffee shop is a must when I'm on vacation. Coffee Tauk definitely delivered on all levels. My latte was served with a genuine smile (how can you not be happy in Montauk, I ask?). It was perfectly presented and, to my delight, strong! We grabbed some healthy snacks and took our coffee to go, so we could walk the beach, which is just two blocks away. I'm bummed I didn't try the gelato, but it was too early in the morning for it...or was it?"
COFFEE TAUK, 83 S. ELMWOOD AVE; 631-668-7007, MONTAUK.
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7 of 10
Ditch Plains Beach

"Because I live in Florida, and I'm used to a certain kind of beach, let's just say my horizons were broadened after visiting Ditch Plains. There's an untouched feeling out there that screams this cool and effortless vibe, one the locals fiercely protect I've learned. And I get it. It's so beautiful in an organic and unpretentious way...a beach that definitely isn't about baring skin and flaunting your bod. It's more about taking off your flip-flops, digging your toes in the sand, and walking along with the ocean breeze in your face and hair. Everything sort of takes a deep breath out there, and stress floats away. Such a magical beach to visit!"
DITCH PLAINS BEACH, DITCH PLAINS ROAD, MONTAUK.
PHOTO: COURTESY OF BEACH TOMATO.
8 of 10
Montauk Bike Shop

"If there is one thing I highly recommend while vacationing, it's renting a bike and pedaling around if the weather permits. My husband and I enjoy seeing the sites this way, and it makes for a good excuse to stop and indulge your inner foodie because of the calories burned! Montauk Bike Shop has it dialed with their choice selection of bikes and gear as well as rentals. They even offer guided tours of the area and have special biking events all throughout the summer. I considered quitting my day job and applying as a guide, but alas, my life in Florida needs me."
MONTAUK BIKE SHOP, 725 MONTAUK HIGHWAY; 631-668-8975, MONTAUK.
PHOTO: COURTESY OF WELL+GOOD.
9 of 10
Duryea's Lobster Deck

"What is a trip to Montauk without a hefty dose of lobster on the menu? I had several insider tips, claiming Duryea's Lobster Deck was the place to go for a hearty Lobster Salad Roll, and I'm happy I followed suit. Soo good! I also recommend the mussels, and if you can, go around dinnertime, so you can relax and watch the sunset settling over Fort Pond and Gardiner's Bay. It's pretty much glorious with a capital G!"
DURYEA'S LOBSTER DECK, 65 TUTHILL ROAD; 631-668-2410, MONTAUK.
PHOTO: COURTESY OF KERI LAMPARTER.
10 of 10
Montauk Point Lighthouse

"Definitely a must if you're visiting Montauk! It's the oldest lighthouse in the United States (1796!) [and] has been a part of Long Island's land and seascape for over 200 years, not to mention it still serves as an active aid to navigation. It's a true piece of American history and visiting it (as well as the museum and gift shop) really set the tone for the trip. It was kind of like the backbone of the trip...without it, everything else might have not seemed so special. I think knowing more about an area and its history is a good way to be charmed when you're visiting other cities. The lighthouse definitely charmed us!"
THE MONTAUK LIGHTHOUSE, 2000 NEW YORK 27 (OFF LIGHTHOUSE ROAD); 631-668-2544, MONTAUK.
PHOTO: COURTESY OF THE MONTAUK LIGHTHOUSE.
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