Cynthia Rowley’s Montauk
Fashion designer Cynthia Rowley has been a regular of Long Island's easternmost point for 12 years and owns a boutique in the town. Here, she describes her perfect day at The End
"My family and I spend most weekends in Montauk during the summer, going to the beach, surfing, and hanging out with friends. We tend to wake up early and walk into town along the cliffs, checking the waves and watching the surfers, before going to Joni’s—the breakfast wrap is amazing and my kids like the waffles. Then we’ll head to our secret beach between town and Ditch Plains to surf and hang out with our friends, Sean MacPherson and Rachelle Hruska.
There are some serious surfers in Montauk: I’ve seen fights in the water and I almost got decapitated by a dude at Ditch Plains three years ago, so if you’re not a pro, my advice is to take a lesson—Air and Speed will hook you up with an instructor, a board and a wetsuit. I’ve been surfing, or as my husband likes to say, “trying to surf”, for 12 years, and I love it. Our secret beach has its own break, so we don’t get in anyone’s way.
We’ll stay at the beach most of the day—everyone brings food—and then I’ll go into town to see what’s going on at my store, and have a slice of crack pie from the pop-up Milk Bar inside it this season.
In the evening we’ll go out on our friends’ boats, and stop off at The Inlet on Lake Montauk for dinner; a great seafood restaurant that does a mean lobster. We end the night at the Crow’s Nest with a few glasses of rosé—it’s my summer cocktail.”
Your options for watching the sun dip into the Atlantic are as plentiful as the surfers paddling on it, thanks to Montauk’s tip of Long Island location. Here are some favorites:
Ditch Plains Beach
Yes, we know drinking on the beach isn't legal—that's what makes it so fun. Grab a bottle of Wölffer Estate rosé from White's Liquor Store in town, wrap a couple of mini-bar glasses in a towel, lay your blanket on the almost empty beach and watch the surfers do their thing.
RELATED: 11 Best Beaches in the USA
The Surf Lodge
The crowd at this converted motel can be a little rowdy late at night, but come early and you'll get a full frontal sunset, reflected in Fort Pond, and a mellow vibe. The punchy Montauket Storm is the must-order cocktail.
Explore More: See hotel details | See all Montauk, NY hotels
Duryeah's Lobster Deck
Sunset, lobster and BYO wine… does it get any better? The plastic tables, paper cups and slightly rude Russian waitresses only add to the experience at this pushing-100-year-old joint, and the shellfish (mussels, Littleneck clams, lobster rolls as well as whole) is literally the freshest in town.
RELATED: How to Do Long Island in Off-Season
Squeeze onto the 3:58PM Cannonball train from New York’s Penn Station and you’ll arrive just in time for a sundowner at this two-year-old bar-restaurant on its own beach a couple of minutes from Montauk Station.
We keep expecting this scruffy pub with a prime bay location to be turned into a luxury hotel—it's been on the market for years. Until then, grab a Blue Point and a picnic table, and try not to stare at Bono if he’s there (we spotted him last July).
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