The Hamptons After Labor Day: 8 Luxury Places Still Worth the Drive
The Hamptons after Labor Day still has plenty of luxury worth the drive, from The American Hotel to Faraway Sag Harbor's new fall package.
Ever since the Covid-19 pandemic, the Hamptons have become less of a seasonal town and more of a year-round destination. However, after Labor Day, traffic noticeably thins, the pop-ups pack up, and half the restaurants that were fully booked in July quietly shift to off-season hours or close altogether. What’s left, at the luxury end of the island, is arguably the better version of the place: real tables, real quiet, and a handful of genuinely upscale hotels, restaurants, and experiences that were never really built for the summer crowd in the first place. Here’s where the drive is still worth it.
Photo Credit: Courtesy of Gurney's Montauk Resort & Seawater Spa
The American Hotel — Sag Harbor
Open every day of the year since Ted Conklin revived the 1846 building in 1972, The American Hotel doesn’t scale back once the village empties; it just gets better. The French-American menu runs foie gras, Peconic Bay scallops, and Long Island duckling alongside a wine list that’s held Wine Spectator’s Grand Award since it was first awarded in 1981. In September, the dining room stops being a summer scene and goes back to being what it’s always actually been: a serious restaurant.
The 1770 House Restaurant & Inn — East Hampton
The 1770 House has always made more sense in the fall. Its below-grade dining room was never built around a sunset view, which is precisely why chef Michael Rozzi’s $85 three-course seasonal prix fixe feels considerably more at home in October than August. Book one of the seven guest rooms upstairs, and East Hampton’s quieter, cozier off-season side becomes the whole reason for the trip.
Jean-Georges at Topping Rose House — Bridgehampton
Topping Rose House runs one of the few full-service luxury hotels in the Hamptons that stays open through the off-season, and its restaurant is the reason to make the trip specifically in fall. The menu draws directly from the property’s own one-acre farm, which means September and October are when the kitchen is actually working with the best ingredients of the year, not the leftovers of summer.
Gurney’s Montauk Resort & Seawater Spa — Montauk
This is one of my absolute favorites in the fall. Gurney’s has billed itself as Montauk’s only true year-round resort since 1926, and it leans into that identity hard once summer ends: fire pits with blankets and heaters, an Autumn Escape Spa Special running September through December, and Indigenous Peoples’ Weekend programming in October. A private beach without a summer crowd on it is its own kind of luxury.
Wölffer Estate Vineyard — Sagaponack
Wölffer’s tasting room stays open year-round, but October is when the property actually shows off, culminating in its Annual Harvest Party, grape-stomping, barrel-rolling, hayrides, live music, timed to the vineyard’s own harvest. Founded in 1988 and now run by winemaker Roman Roth alongside the Wölffer family, it’s the rare Hamptons wine stop that’s genuinely better once the season turns.
Shou Sugi Ban House — Water Mill
The Hamptons’ first dedicated destination-spa retreat stays open year-round, and fall is arguably its best season: fewer guests across the five-acre, 13-studio property, and treatments, sound baths, hydrotherapy, bodywork, that suit cooler weather better than a July pool day does. Founded around a Zen-inspired design philosophy, it’s less a hotel than a genuine wellness retreat, foliage included.
LDV at The Maidstone — East Hampton
The 150-year-old Maidstone reopened in 2024 under LDV Hospitality with an Italian, la dolce vita design overhaul, and chef Jorge Espinoza’s Scarpetta-pedigreed kitchen runs dinner service year-round, including a full October calendar. It’s the rare East Hampton address that pairs real hotel history with a legitimate fine-dining reason to book a table.
Faraway Sag Harbor — Sag Harbor
Formerly Baron’s Cove, the property relaunched under new ownership in June 2026 with 67 rooms, the Amalfi Coast-inspired restaurant Zagara, a heated saltwater pool with firepits, and new padel courts. Its own fall package, “The Season Between,” markets exactly the pitch that defines this whole list: cooler days, a quieter Sag Harbor, and a hotel that’s actually leaning into the shoulder season rather than just tolerating it.
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