Knowing where to start a journey through Upstate New York is no mean feat. It stretches from Manhattan far over the soft folding hills of the Hudson Valley and the superimposing gap of the Hudson River goes on for a while (all the way to Niagra Falls and the Canadian border). Then there’s a bit to the west and a bit to the east of the iconic city-surrounding river, filled with the blue mountains near the Catskills, the watery pools of the Fingerlakes, and a handful of charming old-fashioned towns (we’re looking at you Hudson) to get lost in.
Upstate NY can be a real adventurer’s playground with all the outdoorsy activities — there’s enough to jam-pack a few days with: from cool craft breweries, slick art centres, swish and stylish hotels and shops to splurge in, let's not forget about all the antique barns too. It’s not to be missed, so it’s worth making the time to tag on a trip after visiting the city.
Here’s how to spend 48 hours in Upstate New York — or what to stretch out over a long weekend.
Setting off...
Firstly, rent a car, so you have the freedom to hop in and out at your own pace. Otherwise, it’s a bit scarce for transport and it can be a bit of a struggle exploring on foot for long stretches.
Your first stop? Storm King Art Centre, the open-air contemporary museum in New Windsor that’s about an hour and 15 minutes from the city. Stroll around the grounds for glimpses of big pieces by legends Louise Bourgeois, Alyson Shotz or Mark di Suvero. Head on up to Beacon next, the city was put in the spotlight when the contemporary gallery Dia Beacon opened in 2003. The main street makes for a great break for some souvenir shopping — pop into Little King and pick up colourful wares for the home.
After dark...
Power on through and head up north to a pretty stretch between the Catskills and the Gunks (the Shawangunk Mountains). Checking into Wildflower Farms, Auberge Resorts Collection (rates start from £790, aubergeresorts.com) is a must — a sophisticated out-in-nature cluster of cabins where young couples from the city come to restore and get away from the urban noise.
Lots of care and attention has gone into the build, so much so that earthy huts and modernist cottages blend so well into the mustard-flower-festooned grounds. Drop off the bags, and sit in the Great Porch for a bone broth or a Concord grape sparkling wine before heading back out for a pre-dinner ramble through Kingston. Pop into shops BCMT Co. / Art & Furniture Gallery for one-off pieces, Rough Draft Bar & Books for yes, books and Clove & Creek for lifestyle bits and bobs, before a wood-fired dinner of doughy pizzas and wine by the glass at Lola.
Day 2
Rise and shine, slowly, with a herbal tea in your Adirondack chair on the deck before heading out for a full day. Kick things off in Rhinebeck, a sort of unspokenly interesting, see-and-be-seen town in Dutchess County. This is Clinton territory over here. But before you reach this high street, stop at Rosie General in Kingston (on the west of the Hudson, you’ll realise how much criss-crossing you’ll do) for an open-wide breakfast sandwich of Hudson Valley cheddar, egg and bacon on a toasted English muffin. Be sure to grab a baked good too (the salted chocolate chip cook is something else), or some jarred ferments to pack in the suitcase. Rhinebeck brings the start of antiquing at Rhinebeck Antique Emporium and Beekman Arms Antique Market & Gallery. Happy hunting.
Next make a pit stop in Tivoli. For a quick grab-and-go, head to Tivoli General for toasted mortadella sandwiches and cool merch, or if you need a sit-down, GioBatta Alimentari basically made kale salad a thing. Round out with something sweet, like basil blackberry crumble ice cream at Fortunes. If you are up for it, Hudson is 20 minutes north. You’ll be spoiled for more shopping, The Antique Warehouse, Red Chair on Warren, and FINCH will scratch the vintage itch.
Wind on down and over to Pine Plains, a fairly quiet hamlet with one of the hottest tables to book in recent years. Stissing House is the standalone restaurant from stellar female chef Clare de Boer, who earned her chops folding pasta into creamy buttery sauces at Manhattan’s King before securing an 18th-century tavern to turn into a destination restaurant. But de Boer would rather it be less about the higher-priced menu and more of an appealing watering hole to locals too — she and her husband have a house 20 minutes down the road. On the menu? Densely baked sourdough with whipped butter that comes scooped out from the mounds of buttery towers you’ll spot on tables across dining rooms and on the open-kitchen bar, golden-topped rabbit pie for two, clam chowder and Saltines, and a coconut cake to debate ordering a second slice of.
Day 3
Lie in, go for a swim in the Thistle spa, and then grab a thick order of olive oil pancakes at Clay, the new American restaurant at the hotel. The traffic on the way back can get a bit busy so it’s wise to head off on the earlier side. Stock up on provisions at The Grazery in New Paltz, a 10-minute drive away. Delicious cheeses, crisps of all flavours and crunch, kombucha made locally, or bigger baguette sandwiches for those who are really hungry.
