How to Spend a 3-Day Weekend in Montauk

Summer may be winding down, but there are still a few weekends left – the most important being Labor Day! For my New York City friends, you’re probably desperate to escape the heat and humidity of the city one last time.

Before the leaves start to turn and you swap beach vacations for strolls through the wooded lanes of upstate New York, head out to Montauk. It’s still warm. It’s still less crowded than the rest of the Hamptons. Whether you’ve never been or have a dozen times, make Montauk your last weekend trip of the summer.

In this post, I promote travel to a destination that is the traditional lands of the Montaukett people. With respect, I make a formal land acknowledgment, extending my appreciation and respect to the past and present people of these lands. To learn more about the peoples who call these lands home, I invite you to explore Native Land.

How to Get to Montauk

There are dozens of guides on how you can get to Montauk. On the cheap. The luxe way. The private way. The party way. However you want to get there, there’s a way. Here are the basics.

1. Take the Long Island Rail Road. Leaving from Penn Station regularly, you can hop the LIRR, make one change at Jamaica, and be out to Montauk Station roughly three hours later. Fares start at $20.50 for off-peak travel, or $28.25 for peak travel (one way).
2. Ride the Hampton Jitney. You might recognize it from Sex & the City – the Hampton Jitney is a bus route that takes eager New Yorkers to all the major spots along the Atlantic side of Long Island. To Montauk is $51 round-trip, and it takes a little under three hours.
3. Rent a car and drive. A less popular option due to the fact you’ll have to vie for parking everywhere, you can also rent a car for the weekend in Montauk. On your own, the drive will only take about 2.5 hours. Car rentals start at around $100 for a weekend rental.
4. Private helicopter. Yep, it’s a thing. Blade is an Uber-like company that offers helicopter charters from Manhattan to Montauk. Rumor has it you can snag a seat for roughly $600 one way. #YOLO

Arriving in & Getting Around Montauk

However you arrive in Montauk, there are several important considerations to make. Not all routes are equal: the train deposits you at the Montauk Station, whereas the Hampton Jitney drops you off right in Montauk’s small downtown core.

Based on the movies I’d seen (Eternal Sunshine of the Spotless Mind, anyone?), I assumed that Montauk would be a small but walkable town. As I solicited travel advice, not one person mentioned you need a car to get around.

Let me say that again: You need a car to get around Montauk.

A bike will also do the trick, but honestly, the distances between the major sights in Montauk are sufficient that I’d have preferred a car for moving between places.

Here are your transportation options, in full:

• Rent a taxi. There are lots of taxis in Montauk, but they generally charge a flat rate per passenger depending on where you want to go. This is a quick way to burn up all your spending money, especially if you’re unfamiliar with Montauk and where you want to go.
• Rent a bike. There are several bike rental shops in Montauk, but the most popular is Montauk Bike Shop. As with many popular spots in the summer, be sure to arrive early each day to rent your bike.
• Rent a car. If you want to rent a car, arrange your transport to East Hampton instead of Montauk. There is an Enterprise car rental in East Hampton (don’t believe Google Maps that there’s one in Montauk as it is apparently not always open!) and you can rent a car to drive from there.
• Walk. If you really enjoy walking, you can opt for the one- to three-mile walks between the town, the lighthouse, the harbor, and the train station.

No matter what, assume you’ll need a vehicle to get around. If you want to do sightseeing at all, it will save you money and time in the long run.

Eating, Drinking, and Staying in Montauk

Montauk is a combination of tourist town and local hideaway. As such, they have a quirky combination of food and drink spots that offer acceptable food with great views, and hidden gems that will surprise you. Don’t forget to keep an eye out for local craft beers, like Montauk Brewing Company and Blue Point Brewing Company, on tap most places.

Here are some highlights. (Descriptions in italics are provided by Google.)

Near the Montauk Harbor

• The Clam and Chowder House at Salivar’s – A cool space right on the water with outdoor and upstairs space, as well as a reputed sushi bar.
• Grey Lady – Artisan spot with delicious eats and a menu that focuses heavily on seafood.
• Gosman’s – Great views of the harbor and Long Island sound, this is one of the best spots for seafood in Montauk.

Near the Montauk Beach/Town

• Joni’s – Healthy breakfast & lunch menus feature many organic choices plus fruit smoothies in a quirky cafe.
• Montauk Bake Shoppe– Laid-back bakery for homemade breads & pastries, plus breakfast staples & Italian sandwiches.
• Zu Schneider – Immersive German ambiance and massive menu including German classics done right.

Near the Montauk Train Station

• Montauket – Local spot with a great sunset view and awesome outdoor space for live music.
• Arbor – Laid-back Mediterranean eatery with chic decor & an extensive wine list from a private cellar.

Similarly, there’s a wide range of accommodation options in Montauk. Instead of giving you a comprehensive list, here’s a sample to show you the range.

Budget – Montauk Soundview – Budget is a bit relative in Montauk, as this is a nice, covers all the basics spot. Rooms start around $275/night in peak or $159/night in winter. (Site)

Midline – Montauk Blue Hotel – Casual resort with private pool and tennis, and ocean view rooms. In peak season, they start from around $400/night; in winter, as low as $119/night. (Site)

Luxury – Solé East – Swanky, hip spot in an updated Tudor style building, but with all the modern amenities you need. Rooms start around $500/night depending on the season. (Site)

Oh, Go On and Splurge – Gurney’s – High-end destination resort with everything you need – you might not even want to visit the beach with their beautiful pools.Rates as high as $1000/night in peak, as low as $280 in shoulder, just to give you an idea. (Site).

What to Do in Montauk

Montauk is perfect for a weekend trip because there are plenty of ways to spend your time, but not so many that you’ll feel like you’ve missed out. There will also be things you enjoy doing so much you’ll want to come back at least once per summer.

On the Water

There are plenty of things to do in Montauk, but there are nearly as many to do on the surrounding bodies of water. The northeastern end of Long Island, Montauk is surrounded by both Long Island Sound and the Atlantic Ocean. Want to take a sunset cruise? Mon Tiki can do that for you. Are you a fishing fiend? Head out to the ocean to get the good ones with Double D Charters. You can even opt for standup paddle boarding after renting one at Sunset Surf Shack.

Explore the Harbor

While it’s not a huge activity, the Montauk Harbor is certainly worth exploring. You can see tuna tails nailed up along many of the pylons from successful days of fishing, and watch the seagulls harassing the fisherman as they clean the days catch. Walk all the way out to the inlet to see the various boats coming in and out all day long.

Montauk Point State Park

If the outdoors are always calling your name, be sure to explore Montauk Point State Park and look out to the Atlantic from the tip of Montauk Point. You’ll also have a chance to see the Montauk Point Lighthouse, which dates back to 1796 and the construction of which was authorized by President George Washington.

Head to the Beach

The beach! There’s a reason New Yorkers flock out to the Hamptons and Montauk all summer long – the beaches are a wonderful way to pass the day, especially in the heart of summer when the water warms up and you can really enjoy swimming in the water. You’ll also find surfers out taking advantage of the waves near Ditch Point beach, and lots of shenanigans along the rest of the beach where the resorts are closer to the water line.

Is Montauk on your list for this summer, or are you inspired for next? Let me know any questions in the comments!

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