So you’re heading to the Hamptons for a week. Seven in heaven as we like to say out this way (full disclosure: no one out here says that). But seven days is definitely enough time to get a good taste of what the Hamptons have to offer.
If you need advice about restaurants checkout our dining guide and if you’re still looking for a place to stay, head over to our accommodations guide. If you’ve already got all of that figured out, read on and get ready for a great week.
Day 1: Montauk
We’re going to flip the script and start at The End—as Montauk is fondly known. Why is it known as The End? Because that’s where it is.
The Montauk Lighthouse sits at the easternmost end of Long Island (fun fact: it was commissioned by George Washington) and the surrounding park is a great place to spend a morning exploring. There’s Money Pond where Captain Kidd is rumored to have buried some of his treasure and the old radar dish and the surrounding bunkers from the Montauk Project, which has inspired as many conspiracy theories as JFK’s assassination. Extra bonus: beach hikes where you can spot seals sunning them selves on the rocks and sand surrounding the lighthouse.
As you head back to town, consider stopping at Deep Hollow Ranch, America’s oldest cattle ranch, where you can saddle up and go for a ride. Or, if playing the cowboy isn’t appealing, hang a right and head up to Montauk Harbor. There, you’ll find one of the East Coast’s largest fishing fleets as well as a number of dock side restaurants serving up some of the freshest seafood you can find—it’s literally straight off the boat.
Back in town, a few spots of note are John’s Pancake House, which has serious breakfast and a pretty good burger, too, and Shagwong, which is a popular watering hole and a great place to have dinner. And if you’re around after dark, you’re going to want to stop into the Memory Motel. You may recall hearing of the Memory Motel in the Rolling Stones song of the same name. Don’t be fooled—although they spent time in Montauk at Andy Warhol’s estate, the first time they walked into the Memory Motel they were quickly kicked right back out by the owners. It didn’t stop them from drinking and carousing around town—and they did plenty of that at the aforementioned Shagwong.
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