The Weekend Getaway Guide to Kingston, New York

Renowned for its breathtaking landscapes and vibrant arts scene, the Hudson Valley is home to many charming towns, including Kingston, New York. As the state capital during the American Revolution, Kingston boasts a historic Uptown area, often called “The Stockade District.” Here, visitors can stroll past well-preserved stone houses and Federal-era brick buildings that host an array of independent bookstores, art galleries, and farm-to-table dining establishments—ensuring that the area retains its unique character without the intrusion of chain stores. Meanwhile, the Downtown district, known as the Rondout District, is invitingly located alongside the Hudson River.

But where should you stay, dine, and shop in this enchanting town that blends creativity with culinary delights? Below is your comprehensive weekend getaway guide to Kingston, New York.

Getting to Kingston, New York

The most convenient way to reach Kingston from New York City is by car. The drive is a straightforward two-hour journey up I-87, and having access to a vehicle is ideal for exploring the picturesque Hudson Valley area upon arrival. Alternatively, you can opt for a Trailways bus departing from Port Authority, which will land you in Kingston in just under three hours. If you choose to stay in Uptown Kingston, you’ll find that most shops and dining spots are easily accessible on foot.

Accommodation Options

For a unique lodging experience, look no further than the boutique Hotel Kinsley. This hotel features 42 guest rooms spread across four historic buildings, including a 19th-century structure that once served as the official State Bank of New York and a Georgian stone house dating back to 1680. Despite their historic charm, the interiors are far from outdated—interior designer Robert McKinley has beautifully transformed the spaces using a palette of Farrow & Ball paints, stylish Smeg refrigerators, locally crafted walnut desks, and plaid accent chairs reminiscent of Jacques Adnet’s designs. McKinley shared that his creative vision for the hotel stemmed from a family inheritance story, which resulted in each family member expressing their unique style within a cohesive theme. Plus, the hotel features a fantastic on-site restaurant, which we’ll delve into shortly.

Dining and Drinks

For a cozy dining experience, head to Chleo, a tucked-away wine bar in Uptown that offers a menu centered around open-fire cooking. Dishes like eggplant, lamb, and rhubarb agrodolce, as well as barbecue carrots, are crowd favorites. Don’t forget to inquire about daily specials; earlier this September, their menu showcased a tomato pie with a cornmeal crust. For a sweet finish, the sourdough sundae topped with miso caramel and cocoa crispies is a must-try.

Located in the Downtown waterfront area, Brunette is a charming natural wine bar complete with a dedicated space for artisanal charcuterie and tinned fish. It’s an ideal spot to enjoy a selection of dishes, including trout roe nachos, corn agnolotti, and their indulgent skillet cookie.

Restaurant Kinsley—found on the corner of Wall and John Streets—is the exquisite dining venue associated with Hotel Kinsley. With interiors reminiscent of a stylish 1970s living room, this eatery boasts seasonal menus featuring dishes like squash doughnuts, pumpkin mole tacos, and comforting chicken pot pie with thyme gravy.

For a modern European bistro experience, you can savor cheeseburgers with malt salt fries, perfectly roasted chicken, and a selection of fresh oysters, all paired with a choice of skin contact wines or refreshing cocktails like the Rhubarbarian (rum, lemon, rhubarb syrup, and Velvet Falernum).

If you’re a sandwich lover, swing by the gourmet delicatessen known for its changing seasonal offerings—from pastrami Reubens to tarragon chicken salad sandwiches—alongside their always-available rotisserie chickens. It’s also an ideal spot for those cooking in a rental, offering housemade bacon and an impressive charcuterie selection.

And of course, for any bread enthusiasts, Kingston Bread is the go-to destination for artisan loaves—ranging from cinnamon raisin swirl to jalapeño cheddar batards. Be sure to drop by in the morning to enjoy fresh coffee alongside delectable pastries like apple turnovers and New York-style crumb cakes—the latter being a personal favorite.

Shopping Venues

At Clove & Creek, you’ll discover a carefully curated collection of textiles, clothing, and kitchen items. Here, plaid wool blankets cohabitate with Sea New York sweaters, whimsical copper pots, and elegant wooden candlesticks—all collectively exemplifying the quintessential Hudson Valley aesthetic. Additionally, their own line of natural apothecary products is worth your attention.

Rough Draft is an indie bookstore that soothes the soul. Housed in a charming old stone building from before the Revolutionary War, this bookstore features wooden-beamed ceilings and exposed brick that enhance its inviting ambiance. Grab a latte or a cider and take your time exploring the shelves lined with the latest literary offerings.

For vintage fashion aficionados, Lovefield Vintage is an absolute treasure trove, offering a diverse range of styles, many inspired by the 1960s and 1970s, including pieces sourced directly from Paris.

Lastly, don’t miss out on a delightful flower and decor shop that harmoniously blends fresh blooms with an array of kitchen and garden wares, including ceramics and artisanal soaps that are proudly made in New York.