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STYLECASTER | Things To Do In Montauk
Courtesy of Olivia Marcus.

Before you read any further, I have a confession to make: I’m from the West Coast. I didn’t grow up taking the LIRR out east, I don’t have a sprawling family home in Sag Harbor, and most of my early knowledge of the Hamptons came from episodes of Gossip Girl. Whew! That being said, I am an avid traveler, a proud East Coast transplant and the type of person who does hours of research before visiting any location. When I first experienced the famous Hamptons a few years ago, I was determined to have the ultimate summer experience—even if I was only there for a weekend. Since then, I’ve been back to the Hamptons, and specifically Montauk, a handful of times. Each visit gets better and better. If you’re a Hamptons newbie like me and aren’t totally sure what things to do in Montauk, I present to you: A Beginner’s Guide To Montauk: Where To Stay, Eat, Drink, & Shop. 

If you’re planning a trip to Montauk over a spring, summer, or fall weekend, I hope you are reading this guide in advance of your trip. It may seem obvious, but the best way to guarantee you’ll get a table at The Surf Lodge for dinner on a Thursday night is to make a reservation. The sooner, the better! 

Another hurdle to overcome when planning a trip to Montauk is transportation. Montauk is relatively easy to get around once you get there. There are a variety of options thanks to New York’s efficient modes of public transportation—I know people who rent cars, take the train or the Jitney bus, or even a helicopter to get there. I was able to walk to “downtown” Montauk from my hotel which made it easy to be spontaneous and adventurous. Don’t worry, Ubers are ready and available in Montauk for your evenings out. 

Most hotels also offer some mode of complimentary transportation (I’m talking about a beach cruiser bicycle). But some places take it to the next level—on my most recent trip to Montauk, I stayed at The Surf Lodge and was greeted by a fleet of Land Rover Defenders in the parking lot. Guests were able to use the cars for up to three hours a day free of charge or overnight for a fee. Conveniences like this can be the make-or-break point when deciding where to stay. 

Keep reading for your Montauk weekend itinerary.

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