Weekend Getaway Guide: Montauk, NY (In Autumn)

Montauk is this little beachy town at the very, very farthest tip of Long Island, New York – so far out it’s been coined “the end of the world” (at least in a New Yorkers eye).

It’s beyond the Hamptons and North Fork wine country, and it’s extremely popular in the warm summer months of the year (as is the case for any coastal beach town!).

But surprisingly, I’d never been!

Maybe because I’m always opting for long haul flights across the Atlantic over long hours of traffic across the island. But either way, it’s a destination that kept coming up on my list again and again.

So we finally decided to cross it off. We packed up the car and drove out east, trading the city streets for ocean and beach this past weekend.

Why go during off-season?

Being October, it’s not exactly prime time for Montauk but it still made for an amazing weekend getaway regardless.

If you’re considering visiting and can spare the FOMO of prime time parties, the shoulder season is actually a beautiful time to visit!

  • Less traffic: I’m just going to say it, I f*@&!ng hate traffic. So making it out to the very end of Long Island in 2.5 hours is gold.
  • Less crowds: Without the summer weather, sun worshippers and beach lovers don’t hit up the scene as much (hence the less traffic), so that also means more vacancy, and ability to snag reservations at top restaurants.
  • Cheaper prices: Jacked up prices for the summer months are long gone, and you can usually book a great hotel at a much more affordable price.
  • Good weather: New York in September and October has been unseasonably warm. You might not be in a bathing suit, but you definitely won’t need a parka.

If you’re heading to “The End” for a getaway, here’s my Montauk weekend guide:

montauk weekend guide


Ruschmeyers Hotel is a 5 minute drive (maybe less) from the main strip of Montauk and a perfect little bungalow for a weekend getaway. Cabin-style rooms, retro decor, and a great restaurant right on site!

The hotel closes for the season after October, so get there while you can.


montauk weekend guide


Montauk Bake Shoppe: one of the only real bakeries in the town, so expect long lines at breakfast time but it’s worth the wait. This grab-and-go spot serves up all your baked good dreams.

Mr. John’s Pancake House: A homey little diner on Main Street that serves some big ole pancakes, plus your usual diner stuff.


St. Peter’s Catch: No frills spot with picnic table seating and the freshest seafood.

The Lobster Roll Restaurant: The one with the big LUNCH sign as you’re driving toward Montauk. You probably know it from Showtime’s The Affair, but you should know it for it’s bomb lobster rolls.


Scarpetta Beach at Gurney’s: One of the top restaurants in Montauk serving delicious Italian food. It’s located inside Gurney’s Resort and it’s open all year round – but make sure to make a reservation regardless!

Navy Beach: Navy Beach is much more laid-back with seating on the sand, making it a great spot for catching the sunset. Note that it closes for the season in early October, but totally doable throughout September.


Beaches and pools aside, there are a bunch of other activities and things to do in Montauk, no matter the season. And obviously my first choice has everything to do with wine.

You’ll have your pick of vineyards and wineries in the North Fork area, from Wölffer Estate to Channing Daughters. Do a tasting overlooking the vineyards, snack on some cheese, and stock up on bottles to drink back home.

montauk weekend guide

Montauk Point Lighthouse

One of those things you just have to do when visiting Montauk. It’s legit the furthest most tip, and it’s a historic landmark. Plus, you can actually climb all 130+ stairs to the top!

Bonus of visiting during the off-season, the lines to the top are very short and there’s basically now wait.

Visiting the Montauk Brewery Tap Room is one more activity you should definitely make time for when in Montauk.

You’ve definitely heard of drank their beer, so it’s cool to see where it all started. Their Tap Room is actually an old schoolhouse converted into a brewery. Go by for a flight, taste their variety of seasonal beers on tap, or pick up a growler to go. Cheers!

That wraps up one way to experience Montauk in a weekend, especially if you opt to visit during the off-season!

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