Home Destinations How to Spend a Weekend in Montauk

How to Spend a Weekend in Montauk


Everyone loves New York, but let’s be real – as beautiful as Central Park is, no matter what way you twist it, it is not a beach. In the upcoming summer months it will become more apparent that “concrete jungle” is not an exaggeration. Lucky enough for New Yorkers, the typically dreaded trip on the LIRR to that appendage of Manhattan called Long Island becomes much more appealing. Why you ask? At the very eastern tip of the seemingly wasteful land of suburbia is a little vacation destination called Montauk.

Need a getaway from New York City? All you need is 48 hours and the mind of an adventurer. Buy a weekend bag, pack it, and waste no time getting to the quaint beach town for the weekend. It might just be the refresher you need to find the strength to utter the words “good morning” on Monday when you return to work.

How to Get There

Montauk Railroad Station LIRR


Most New Yorkers do not have easy access to cars, but no worries! Montauk is accessible via the Long Island Rail Road (yes the dreaded LIRR). All you have to do is get a train from Penn (or a nearby subway) and make a transfer onto the Montauk Line at Jamaica Station. From Jamaica, it is smooth sailing to the Montauk train station. On the bright side, the train bypasses all the summer traffic headed to Montauk for the weekends. If you’re not into the train, the Hampton Jitney bus line brings city people to the southeastern tip of the island. It is a bit more expensive, but hey, you win some you lose some.

What to See

Montauk Lighthouse


Once you get to Montauk, you will more than likely be overjoyed to see an actual beach, with waves, seagulls, and sand that isn’t dirt. Feel free to enjoy all that the beach has to offer, but Montauk has a few more must-sees within your 48 hours:

The Montauk Lighthouse: The Montauk Lighthouse is one of the oldest structures in the United States. It is a little bit of a hike to get to, but if you time it just right, getting there at sunset for a climb up will make the whole weekend worth the painful memories on the LIRR (side note: I actually thoroughly enjoy riding the LIRR, so maybe you will too).

Montauk Town: Montauk is the epitome of an adorable beach town. If temperatures didn’t drop to below zero during the winter, I bet people would actually love to raise their kids there. It has a ton a great shops to mosey around and really gives you the small town feel you miss you in New York. Reminder: I say mosey because you are supposed to be relaxing. Relax!

Fishing: A long time ago, before corporate America killed all small businesses, Montauk actually was a major fishing town for New York. Take part in a little tradition by taking a half-day boat ride. You don’t even have to fish, just enjoy the ride on the water.

Montauk Harbor: Get some ice cream and take a stroll around Montauk Harbor at night. Revert back to the days when watching boats set sail was considered a fun activity.

Beaches: Ditch Plains Beach, Gin Beach, and Hither Hills State Park are the best beaches to spread your towel out. Some of the beaches in Montauk are for private residents, but as long as you stick to these three, you won’t be arrested on your relaxing weekend. Enjoy the sun, watch (or try) surfing, take a bike ride. This weekend is all about getting in touch with the beach bum that lives inside you.

Where to Stay

Montauk Yacht Club Hotel

If you are not renting a house in Montauk, fear not, there are plenty of hotels to find adequate lodging.

The Montauk Yacht Club: You may have to turn your noes up a bit, but I am assuming since you are coming from the city you don’t have a problem doing that every now and again. This hotel has some of the nicest rooms and facilities of any hotel in Montauk, but since it’s right on the harbor, the views are incredible. If it’s good enough for Bethenny Frankel, it’s good enough for you.

Some other well-rated hotels include:

Montauk Manor
Ocean Beach Resort
Sole East Resort
Panoramic View

Where to Eat

Gosman's Restaurant Montauk


The most important part of any vacation is indulging in the calories you swear off during the week:

Gosman’s Restaurant: Right on the water, Gosman’s is a great mix of American and seafood. Ask for outdoor seating so you can enjoy your meal right on the dock.

Harvest on Fort Pond: This restaurant is pricier, but it is family style. It’s seafood, but what else did you expect from a beach town?

The Gigshack: A local outdoor cafe sort of restaurant. It is open for breakfast, lunch, and dinner, but it is a great place to stop after the beach. It is also a great place to finish up dinner and start drinks.

John’s Drive-In: The restaurant is a 1950′s style burger joint. From personal experience: I will swear by John’s Drive-In ice cream for the rest of my life. It’s delicious and the perfect dessert for a summer day.

Where to Drink

The Bar at the Surf Lodge in Montauk New York


The Bar at the Surf Lounge: A bit posh, but this is your getaway so indulge! Try the Lakeside Punch, after two you won’t even know how much money you are spending.

The Den at the Surf Lodge: A low-key and comfortable bar that will make you feel right at home.

The Liar’s Saloon: A local bar with Karaoke. Need I say more? I know you are picturing your sun burned self singing “Man, I Feel Like a Woman” in flip flops and a cowboy hat… and you love it.

So get away to Montauk! I promise the trek from the city will be worth the memories.



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