Escape from New York: Our Favorite Fall Getaways
Sure, a summer getaway is a must, but come fall, there’s another reason to get out of New York: the sheer beauty of it. The Catskills are practically made for leaf peeping, the Berkshires turn into a kaleidoscope of red and gold, and Connecticut has plenty of pastoral New England charm of its own. And if your idea of communing with nature still involves a good restaurant and somewhere to get a martini, there’s always Hudson.
Whether you want to spend the weekend hiking through the woods, sitting by a fire, soaking in a hot tub, or wandering around town pretending you might actually move upstate, we’ve got you covered. Here’s our guide to getting out of the city and taking full advantage of all that autumnal beauty the Northeast has to offer.
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The Leeway
Just over two hours from Manhattan, The Leeway sits on six acres along the Esopus Creek in Mount Tremper, conveniently located between Phoenicia and Woodstock. The cabin-style suites come with full kitchens, private decks and wood stoves, combining the autonomy of a self check-in with the luxury of a genuinely well-designed place to stay. Think lots of pine, wool and stone, with big windows looking out onto the woods and river.
There’s no restaurant on the property, but good news: the Phoenicia Diner is a mere four-minute drive away, and Woodstock’s restaurants aren’t much further. And don’t worry, you won’t wake up without coffee—that comes provided. But if you want to do The Leeway the right way, grab a bottle of local cider and head down to the creek, where Adirondack chairs, fire pits and mountain views make it an ideal place to sit in silence, breathe in the fall air and do absolutely nothing. If you do feel like leaving, hiking trails, the Ashokan Reservoir and plenty of good food and live music are all within easy driving distance.
Mt Tremper, NY; (845) 420-3600
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Prospect Berkshires
And if you’ve had enough of upstate New York, there’s always the Berkshires. Specifically, Prospect Berkshires, a lakeside retreat in Egremont, Massachusetts, with 49 minimalist cabins set among the woods of Prospect Lake. In the fall, that means plenty of foliage to take in between kayaking, tennis, pickleball and hikes—or from the comfort of one of the property’s wood-fired soaking tubs.
There’s also a year-round heated saltwater pool, lakeside sauna, cold plunges and wellness offerings ranging from yoga and breathwork to massage. Come evening, head to The Cliff House for locally sourced food and mountain views, or settle in around one of the fire pits. Nearby Great Barrington has restaurants, bookstores and vintage shops should you feel like venturing off property, while Bash Bish Falls and Catamount offer even more reasons to get outside.
Egremont, MA; (413) 528-5005
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Spruceton Inn
Spruceton Inn is one of those places you almost have to know about to find—and once you do, you’ll be amazed by just how serene this little corner of the Catskills is. Set on eight acres along the West Kill Creek, the nine-room inn is surrounded by meadows and mountains, with hammocks, fire pits, grills, an itty-bitty bar and some truly unbeatable stargazing. It’s also something of an artists’ haven: run by writer Casey Scieszka and artist Steven Weinberg, the inn hosts an annual artist residency each fall, while its restored barn doubles as a neighborhood library and space for art shows and other events.
And while those eight acres are well worth exploring on their own, nearby you’ll also find Diamond Notch Falls, one of the most beautiful—and surprisingly peaceful—hikes in the Catskills. Afterward, stop at West Kill Brewing for a post-hike beer before heading back to the inn, where you can grab a drink at the bar (half of its profits go to social and climate justice nonprofits) and spend the evening by the creek or around one of the fire pits. Mornings come with Café Grumpy coffee and Pop-Tarts. One thing to keep in mind: Spruceton keeps rather limited hours, generally opening for weekend stays from Memorial Day through October, so plan accordingly.
West Kill, NY; (518) 989-6404
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Pocketbook Hudson
If you love the idea of a fall getaway but aren’t exactly a cabin-in-the-woods person, Pocketbook Hudson may be more your speed. Housed in a sprawling former textile and pocketbook factory just off Hudson’s main drag, the 46-room hotel has everything from a beautiful open-fire restaurant to galleries, a café and bar, a subterranean nightclub and a communal bathhouse complete with steam rooms, cold plunges and saltwater pools. There’s also a rotating lineup of wellness classes, workshops and other programming, should you require a little more activity than staring at foliage.
Better yet, Hudson gives you plenty to do beyond the hotel, with restaurants, galleries, antique shops and boutiques all packed into a very walkable two square miles. And for those of us who would rather not rent a car, you can take the train straight from the city and leave the driving to someone else.
Hudson, NY; (518) 660-0885
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Lost Fox Inn
For even more uncharted territory, Litchfield, Connecticut, seems to be having a bit of a moment. The pastoral New England town has quietly amassed an impressive food scene and a growing crop of boutique hotels, including Lost Fox Inn, a romantic, slightly bohemian property just outside of town.
The team behind Catskills favorite Foxfire Mountain House transformed a historic 1740s tavern into an intimate retreat filled with antique furnishings and artwork, stone fireplaces and soaking tubs. The aesthetic takes some unexpected inspiration from the Rolling Stones’ famously decadent stay at Villa Nellcôte in the South of France, mixing the feel of an old French chateau with a little rock-and-roll spirit. There’s also a formal garden and an excellent tavern and restaurant serving New England-inspired fare. And with Litchfield’s rolling hills, lakes and foliage surrounding you, it all feels particularly well suited to fall.
Litchfield, CT; (860) 222-0855
WORDS Hillary Sproul
PHOTOGRAPHY The Leeway