7.18.2017

Where to Eat and Drink on Your First Visit to Montauk, Off-Season

After a seven hour road trip from Washington, DC, I pulled in to Montauk with an agenda. Like I normally do, I'd been keeping track of restaurants and places I wanted to visit. And then... Montauk had other plans for me.

Since I was there the week before Memorial Day, most of my targets weren't yet open. 

This forced me to live more like a local. And, I loved it. 

After dropping our bags at our house, Thea and I called a cab, chasing the sunset. Since all of the spots we had planned to go to were closed, we left our destination up to our cab driver and he lead us to my favorite place for the week: The Montauket


The building and bar is nothing fancy (like I like it), but. this. view. 


I ordered a glass of the local rosé (the first of many times I'd drink Wolffer Estate Summer in a Bottle that week.) 

At the close of each day, I'd hop in the MINI and zip over to The Montauket for a glass of wine and sunset. Perfection. The bartenders remembered my name the second time I showed up - and what I was drinking. I met locals and Long Islanders, which I found far more interesting than the snobby Goldman Sachs banker that talked loudly about his Miami house and how much money he made. The Montauket became home base.

On the food-front, there were a lot of great options. Some of my favorites were Duryea's for lobster rolls, crispy french fries and bottles of rosé on the dock, 668 The Gig Shack for lunch at the bar and John's Pancake House for hot breakfast. 

My favorite single food moment was zipping down to see if Gosman's was open for lunch yet (it wasn't) and finding Sammy's On The Go food truck for a fried clam roll on a perfect spring day. 

Fried Clam Roll from Sammy's On The Go
Another great afternoon spot for fried seafood is The Clam Bar, just off the main road into town. 

Fried Clams, Sweet Potato Fries and a Diet Coke from The Clam Bar
Looking for the perfect latte in Montauk? You'll want to find Left Hand Coffee (it took me a few days.)

If you want your coffee straight up and with a side of decadent baked goods, head to Montauk Bake Shoppe. I was a regular there for their croissants, which I'd bring home and eat on the deck while I worked.

Coffee and Chocolate Croissant at Montauk Bake Shoppe
Looking for a way to spend a cloudy day? The Long Island wine scene has come a long way. I'd recommend a tasting at Wolffer Estate. It's a beautiful vineyard and tasting room, with beautiful charcuterie boards and a full menu. I dare you to leave without buying a bottle of their rosé.

Wine Tasting at Wolffer Estate
Another fun road trip was meeting friends for brunch at Estia's Little Kitchen in Sag Harbor. It's a beautiful drive and at the culmination, you're rewarded with decadent, fresh Mexican eats. When someone inevitably asks, "Should we also get queso fundido?" Everyone should respond with a resounding "YESSSS!" There are no reservations, so plan for a bit of a wait here. Luckily, there are cool gardens and patio tables to hang out at while you wait.
Estia's in Sag Harbor
On a clear day, you'll want to visit the Montauk Lighthouse. You can go all the way to the top - or just hike around the cliffs and rock beaches nearby. Either way, the views are breathtaking.

Montauk Lighthouse
For the days where you just want to lay in the sand and read or soak up the sun, my favorite was Ditch Plains Beach. In the summer, this spot is probably crazy busy. But, Ike and I were rewarded with vast open stretches of beach to run on. I liked this neighborhood a lot. I'm sure the real estate is still out of my price range, but the houses are more down to Earth in this part of the town. 

Ditch Plains Beach
Montauk reminded me a lot of Key West. Both of them feel like the ends of the Earth. Both have fantastic people and places when you dig beneath the overlay of drunken tourists. I feel so thankful that I was able to see it first without the lens of the influx of investment bankers and trust funds. 

I hope one day, I'll return. 


Huge thanks to Mattie Matthews for allowing me a peek into Montauk life, for making me laugh consistently for years, and for being there as we support each other in this crazy life. PS. You need to be following her on Twitter and reading her blog, 67 and Dumped. Start at the beginning if you're new. Oh yeah, and she also is an award-winning travel writer.


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