The Most Luxurious Fall Weekend Escapes From New York, From Hudson Valley Farms to the Hamptons
Best fall weekend escapes from New York: Wildflower Farms, Topping Rose House, Troutbeck, Shou Sugi Ban House, INNESS and Oyster Estate.
Photo Credit: Courtesy of Wildflower Farms, Auberge Collection
October is the best month to leave New York for the weekend, and the best fall weekend escapes from New York are all an easy drive from Manhattan. The Hudson Valley turns copper, the North Fork brings in its harvest, and the Hamptons, emptied of the summer crowd, finally remember how to be quiet. These are the luxury hotels to book now, along with the farm dinners and harvest days worth planning around. Every one rewards arriving on Friday afternoon, before the traffic, and leaving as late on Sunday as checkout allows.
Wildflower Farms, Auberge Collection — Gardiner, Hudson Valley
Photo Credit: Courtesy of Wildflower Farms, Auberge Collection
Auberge’s Hudson Valley retreat sits on 140 acres where the valley meets the foothills of the Catskills, with views to the Shawangunk Ridge. Its 65 freestanding cabins, cottages and suites come with fireplaces, wood decks and outdoor fire pits. A 100-acre farm feeds Clay, the progressive American restaurant, and the cooking-school barn runs a weekly calendar of events. Fall is for forest foraging, Nordic bathing and a long treatment at Thistle, the Auberge spa.
2702 Main Street, Gardiner, New York
Topping Rose House — Bridgehampton
Topping Rose House calls itself the only full-service luxury hotel in the Hamptons, and it stays open after the summer crowd leaves. The 19th-century mansion holds 16 rooms and six one-bedroom suites, made up with Frette linens and Matouk towels. Jean-Georges runs the restaurant year-round, cooking with produce from local fishermen and farms, and a car shuttles guests to the beach. October here means empty roads, a heated pool and a table you could never book in July.
One Bridgehampton–Sag Harbor Turnpike, Bridgehampton, New York
Troutbeck — Amenia, Hudson Valley
Troutbeck is a 250-acre estate hotel with a 250-year history of hospitality, crossed by the Webatuck River and Dunham Creek. Rooms come with Frette linens and breakfast in bed. Days can be spent fly fishing, riding or cycling the hotel’s complimentary bikes to Millerton and Sharon, Connecticut, and the dining room cooks to the season. It suits a guest who wants a fireplace, a good book and the sound of the creek.
515 Leedsville Road, Amenia, New York
Shou Sugi Ban House — Water Mill
Photo Credit: Courtesy of Shou Sugi Ban House
For a Hamptons weekend centered on wellness, this gated, wabi-sabi compound in Water Mill is a 12-room retreat and spa. It is named for the Japanese technique of preserving wood by charring it. The program covers yoga, meditation, hydrotherapy, bodywork, and a full culinary program, three miles from the ocean. In the off-season, with the farm stands still open and the beaches deserted, the stillness makes the most sense.
Water Mill, New York
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INNESS — Accord, Hudson Valley
INNESS spreads 28 private cabins and a 12-room Farmhouse across 220 acres with views of the Catskills. The Grand King Cabins have wood-burning fireplaces and floor-to-ceiling windows. The restaurant cooks Mediterranean-inspired dishes from the valley’s harvest, with handmade pastas and natural wines, and the bathhouse has a heated tranquility pool, sauna and steam room. Golfers get a King Collins–designed nine-hole course, best played on a cool October morning.
10 Bank Street, Accord, New York
Oyster Estate — Greenport, North Fork
Photo Credit: Matt Kisiday
Blue Flag Capital opened Oyster Estate in Greenport in September 2026. The 34-room house was redesigned with Islyn Studio, and local flowers are pressed into its lobby tiles. Make it the base for a harvest weekend. On Saturday, October 24, RGNY in Riverhead invites guests to hand-pick grapes for its 2026 vintages, with wine, bites and a toast afterward, and the vineyard’s Día de los Muertos celebration closes the season on November 7.
326 Front Street, Greenport, New York
For more of Haute Living’s fall travel coverage, see the best luxury hotels in America for a fall weekend and the Hamptons after Labor Day.
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Frequently Asked Questions
What is the best luxury hotel in the Hudson Valley for fall?
Wildflower Farms, Auberge Collection, in Gardiner, with 65 cabins, cottages and suites on 140 acres.
Are Hamptons hotels open in the fall?
Yes; Topping Rose House and its Jean-Georges restaurant are open year-round.
When is RGNY's harvest day?
Saturday, October 24, 2026, at RGNY in Riverhead.
How many rooms does Topping Rose House have?
16 guest rooms and six one-bedroom suites.
Where is Oyster Estate?
326 Front Street in Greenport, on the North Fork; it opened in September 2026.
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