Nowadays, when people hear “The Hamptons,” they tend to retort with, “so overrated.” But before influencers swarmed East Hampton like locusts—and now, Montauk—it was my family’s little happy place. My fondest memories consist of me and my sister gallivanting through the shops—sneaking extra donuts from Dreesens—while Dad disappeared into the Montauk Bookshop (gone now) and Mom deliberated over a woven bag from Calypso (also gone). At 5 p.m., we’d all meet outside for dinner and a debate about which VHS we were renting from Video Hampton—one of the last great indie rental stores on the island. But eventually, the boutiques shuttered, the bookshelves were boxed up, and Instagram caught wind of the famous Dreesens donuts. 

Main Street now looks more like Fifth Avenue, with Louis Vuitton and The Row replacing my favorite boutiques. What was once charming and offbeat now feels curated and built for social media. Which is why, when my boyfriend and I booked a last-minute trip to the North Fork, I wasn’t expecting much. But after two nights at The Harbor Front Inn in Greenport, I felt like I’d time-traveled. It had all the charm I was craving—quiet, coastal and just the right amount of nostalgic—without an ounce of pretension.

So below, find everything you need to know about the stay, the town, and how to spend a perfect weekend in Greenport—from a reformed South Fork loyalist who now knows better.

Beach Butlers, Dyson Dryers and a $58 Lobster Roll: Inside My Girls’ Trip to The Colony Hotel

 7 of Our Favorite Hotels for Every Hamptons Scenario