A Poor Man's Guide to the Hamptons

I should start by saying this not a “guide” to the Hamptons in the traditional sense. I’ve spent far too little time on the Southern stretch of Long Island to feign familiarity.

Readers looking for smarter intel would be much better served subscribing to Rory Satran’s excellent newsletter, The Hamptons Chronicle, or perusing NY Mag’s recent Hamptons Issue for all the palace intrigue and in-fighting expected from a place where the ultra-rich bump up against one another in hilarious ways.

Prior to this past weekend, I had visited Montauk once, for a blustery spring excursion with my wife and youngest son. It was a several years ago, in late March, when the roads, beaches, and businesses were empty. We spent a week at a rented cottage out by Crow’s Nest, cooking, walking on the beach, sitting by the fire, and exploring.

Highlights from that particular trip were beers at Shagwong, lunch at Carissa’s, browsing at Wyeth and the now-closed Tiina the Store, visiting Parrish Art Museum in Water Mill, and hiking out to the bluff’s edge at Amsterdam State Park for a glimpse at some of the Seven Sisters in one direction, and Eothen, Warhol’s old compound, in the other.

Two years later, I spent a long weekend at a friend’s beautiful house in Sagaponack. He may have lived in the Hamptons, but he was not of the Hamptons (a popular refrain, I’m learning). We mostly spent our time going on morning runs, thrashing about in the ocean, cooking, and playing Backgammon.

Both visits were out of season, but I was left with a strong impression of the beauty that attracts people to this stretch of Long Island - the old growth trees, thick canopies, lush hedges, dense grasses, and dancing dunes - but not much understanding of the social dynamics at play beyond a drive down Lily Pond Lane and the glimpse of a particular breed of rich beyond my comprehension.

This is A Poor Man’s Guide to the Hamptons, because in the Hamptons, even the rich are poor. No matter what you’ve got - someone else has more.

We spent the weekend between East Hampton (in an overpriced Bed & Breakfast) and Amagansett (hosting a trunk show with 180 the Store), with a visit to the vaunted Maidstone Club, plus jaunts to Montauk and Sag Harbor for private events, the best way to eat when you’re a poor man “out east.”

Here’s my take: