How To: Hamptons After Tumbleweed Tuesday


IMG_3249Photo Credit: PaintingTheHamptons

With Tumbleweed Tuesday sending the bulk of Hamptonites shuffling back through traffic to the city, it’s never been a better time to get out to the Hamptons. All the tourists are gone, the beaches are open, and you rarely need to make reservations anymore even! While mid-summer the Hamptons can require about an hour wait to do anything from find parking to get your appetizer, the post-Tumbleweed Tuesday crowd knows that the temperature doesn’t drop to nothing one day later, but all the crowds sure do. Here’s a quick guide to the best things to see and do out East before the winds of winter start picking up.


Where To Stay:

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Ever look into the rearview side mirrors on your car? Images are closer than they appear? That’s what the Hamptons is off-season. What was an 8-hour-if-we’re-lucky commute to Montauk is now a 2 hour drive down empty highways. Which means that hotels take on a new meaning and an added luxury. They’re no longer the necessities that they were before; with 9:00am check out times so they can turn over for the next wall-to-wall booking. They’re more relaxed and easygoing, and here for you. Haven, Montauk’s laid-back surfer-inclined hotel, is in Montauk just off the water, and the perfect breezy spot to walk to the water, or the bar. The hotel definitely leans into the local scene, and finds its better features in keeping things simple for your stay. The staff members are, arguably, the greatest people in the Hamptons. (Editor’s Note: I once almost missed my train, and the guy behind the desk said, “Hop in my truck, I know a short cut.” There was no locking up, no asking someone to cover, he was genuinely concerned about my making that train, and I did.)


Where To Eat:

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There is only one cuisine anyone needs in the Hamptons, and that’s seafood. The Hamptons boasts some of the best fishermen on the East Coast, and supply tons of New York restaurants, so eat the freshest fish of the season directly from the source! While everyone else may be prematurely drinking pumpkin spiced everything back in the city, treat yourself to one last cocktail garnished with an umbrella and a preposterously big slice of citrus fruit. While Eleven Madison Park’s summer pop up, EMP Summer House, was the Rookie of the Year this past summer, other top-notch new restaurants are sticking around to hone their craft. Flagship, in Montauk, is built for success with great fish and raw bar options, gourmet takes on classic beach dishes, and a social-media conscious design that’s perfect to light up your feed.


Where To Swim:

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Ditch Plains. The paramount Hamptons beach for young people looking to hang with fellow young people, Ditch Plains Park is the perfect spot to have a burrito, play some Frisbee, or walk a little further down the coast and catch some waves surfing.

Where To Go Out:


While it’s been known for a rowdy, young crowd in the past, The Surf Lodge has endured for a reason: it’s unparalleled in its ability to have fun and let loose. The Surf Lodge, ten years into its non-stop successful run in the Hamptons, brings in big names in music for its summertime concerts, a programming schedule that’s done so well, bands are still signing on into the fall months. While there’s a hotel upstairs, the best part of The Surf Lodge is the outdoor bar and concert series.


Where To Go Out (Classy Edition):

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For the older crowd, who have been coming to the Hamptons for years and experienced their long nights at the Surf Lodge already, going out may mean something a bit more refined. Look no further than Wolffer Estate Vineyard. This winery has been growing in popularity more and more every year in the city, but has always been the go-to destination for wine out East. With new locations of their full restaurant Wolffer Kitchen opening in Amaganssett, the winery is ever-expanding and the perfect place to get ready for fall while looking out over the vineyard trees.