A Guide to Kingston, New York: The Quaint Hudson Valley Town Meant for Idyllic Fall Getaways

The reason Hudson Valley has an idyllic reputation in the first place is because of towns like Kingston, New York. The capital of New York state during the American Revolution, Kingston’s historic Uptown (also called “The Stockade District”) is dotted with stone houses and Federal-era brick buildings which house bookstores, art galleries, and farm-to-table restaurants. (No chain store or private equity backed coffee shop in sight.) Meanwhile, the Downtown area (also known as the Rondout District) is nestled right on the banks of the Hudson River.

So where do you stay, eat, and shop in this storybook town known for its artistic offerings and farm-to-table dining scene? A weekend getaway guide to Kingston, New York, below.

How to Get to Kingston, New York

The easiest (and best) way to get to Kingston, New York from New York City is to rent a car—not only is essentially a two-hour straight shot up I-87, but you want to drive around the Hudson Valley region once you get there. (Ubers are not really a thing.) That being said, you can also take a Trailways bus from Port Authority that will get you to Kingston in under three hours. If staying in Uptown Kingston, most of the shops and restaurants will be within walking distance.

Where to Stay

Hotel Kinsley in Kingston, New York.Photo: Nicole Franzen

The boutique Hotel Kinsley’s 42 guest rooms are spread across four historic buildings, including a 19th-century structure that housed the official State Bank of New York and a Georgian stone home that dates back to 1680. Though archaic, out-of-date lodgings these are not: the interiors are by the masterful Robert McKinley of Studio McKinley. He painted the guest room walls in Farrow & Ball shades and decorated them with Smeg refrigerators, walnut desks made in Red Hook, and plaid chairs that wink to Jacques Adnet’s. (McKinley previously told Vogue that his visual inspiration was the following: “An extended family inherited the property from their grandmother—the sole stipulation of the inheritance being that the family must develop a cohesive hotel that highlights each of their unique styles. In doing so, each family member was assigned a different building, which allowed them to pursue their own aesthetic fantasies while also adhering to a common thread.”) An added bonus? The excellent on-site restaurant—but more on that later.

Where to Eat and Drink

Photo: Read McKendree

A tiny wine bar in Uptown that cooks food over an open fire, Chleo is the quintessential cozy restaurant in Kingston. You can’t go wrong with the eggplant, lamb, and rhubarb agrodolce and the barbecue carrots—but hear out the specials before you make a decision: in early September, for example, they served up a tomato pie with cornmeal crust, whereas the spring saw a soft shell crab land on the menu. For dessert, go for the sourdough sundae with miso caramel and cocoa crispies.

In the waterfront Downtown district of Kingston is Brunette, a charming natural wine bar that has a dedicated section for both charcuterie and tinned fish. Order all of that, plus the trout roe nachos and the corn agnolotti—just make sure to save room for the skillet cookie for dessert.

On Wall and John Streets is Restaurant Kinsley, the excellent F&B offering of Hotel Kinsley. The interiors, with their velvet couches and biophilic design, feel like the 1970s living room of the coolest person you know. Like most of the restaurants in the Hudson Valley, the menu changes with what’s in season—right now, that’s squash doughnuts, pumpkin mole tacos, and a chicken pot pie with thyme gravy.

A modern, European-style bistro where you can get a cheeseburger with malt salt fries, a perfect roast chicken, and a tray of oysters. Pair it with a skin contact wine, a cider, or their Rhubarbarian cocktail (rum, lemon, rhubarb syrup and Velvet Falernum).

A gourmet delicatessen that specializes in offering the best sandwiches—and much more—from local meats and produce. The menu is ever-changing due to seasonality (this week they’ve got a pastrami Reuben and a tarragon chicken salad sandwich) but they always have rotisserie chickens on hand. For those staying in a home with a kitchen, swing by for the best deli meats and specials (they offer housemade bacon) as well as their vast charcuterie selection.

As the name suggests, Kingston Bread serves bread and a lot of it: choose from a mouthwatering array of loaves from cinnamon raisin swirl bread to a jalapeño cheddar batard. In the morning, wander over for coffee and a fresh gourmet pastry like apple turnovers, cardamom buns, and (this writer’s favorite) a New York style crumb cake.

Where to Shop

Clove and CreekPhoto: Genevieve Garruppo

Clove & Creek offers a variety of curated textiles, clothes, and kitchenware: plaid wool blankets lay among everything from Sea New York sweaters to copper pots and wooden candlesticks. It may seem like a wildly eclectic assortment, but it makes perfect sense once you are inside—everything fits in the Hudson Valley bucolic aesthetic. They also sell their own natural apothecary products.

There’s something about Rough Draft that calms your soul. Maybe it’s the surroundings, both inside and out: housed in an old stone building that pre-dates the Revolutionary War, the interiors feature wood-beamed ceilings and exposed bricks. Or maybe just because it’s a fantastic indie bookstore in an age where fantastic indie bookstores feel few and far between. Order a latte—or even a cider—from their café and peruse the latest titles on its historic shelves.

Every small town needs a good vintage shop. Lovefield Vintage delivers and more, even bringing back clothing sourced straight from Paris. Their offerings run the gamut, but many of them exude a ’60s and ’70s flair.

In this flower and decor shop, blooms sit alongside kitchen and garden wares—including vases by Sharland England and bowls by Les Ottomans. They also take great care to highlight New York-made products, from ceramics to soaps.