A Guide to Kingston, NY

Ninety miles north of NYC, the Hudson River Valley town of Kingston, NY sits at the base of the Catskill Mountains on the Rondout Creek.

As New York’s original capital, it’s loaded with history and incredible architecture — but today, it’s equally defined by a vibrant art community and a wave of new restaurants, shops, and cultural spaces.

Divided into three walkable neighborhoods — Uptown, Midtown, and the Rondout — each has its own rhythm, from the painted facades and vintage storefronts of the Stockade District to Midtown’s creative edge and the charming waterfront of the Rondout.

Whether it’s browsing antiques, catching a gallery opening, kayaking the creek, or dining in spaces that feel straight out of the city, Kingston continues to evolve as one of the Hudson Valley’s most dynamic destinations.

Wall St in Uptown Kingston, NY is lined with boutique shops, galleries and restaurants.

Much of Kingston’s appeal is being at the epicenter of “Upstate” culture in the Hudson Valley. Exploring town, and the region, is a must! The town is comprised of three distinct neighborhoods: Uptown (also called the Stockade District), Midtown, and the Rondout (downtown.)

Uptown Kingston is the most architecturally distinctive, with colorful painted buildings facades along Main and North Front Streets – plus some exceptionally preserved historic buildings in the blocks surrounding. In this part of town, don’t miss staples like Kingston Consignments (consignment & antiques for the home), Rhino Records (vinyl, books & curios), Lovefield Vintage and Capital Vintage (two spots with great hand-picked vintage), Blue Cashew (kitchenware) and Hamilton & Adams (women & menswear.)

In Midtown, Kingston’s more industrial neighborhood is probably the epicenter of its creativity, where many artists and entrepreneur-types have taken up residence and have studio spaces in old factories. Keep your eyes peeled for the murals in this part of town, whose number grow every year thanks to Kingston’s annual O+ Festival. While in Midtown, don’t miss Zaborski Emporium, a massive warehouse filled with antiques and architectural salvage stuff for the home; vintage clothing, furniture, and decor at Red Owl; and L’Impatience‘s modern ceramics. Or, skip all that and zen out in a sensory deprivation tank at Zephyr Float.

Last, the Rondout (downtown) neighborhood is perhaps Kingston’s most idyllic, boasting some serious old-world charm. Its main street, Broadway, is a slope lined with cute shops and cafes including some favorites like Kingston Wine Co., Clove & Creek, Milne, and Hops Petunia. From here, stroll down to the Rondout Canal, which cuts along old railroad tracks while taking in the stunning views of the Hudson. Galleries of note in this part of town include One Mile Gallery, Artport Kingston, and Monument.

Awosting Falls in Minnewaska State Park Preserve.

For those looking to stretch your legs a little, Kingston NY is super central to some of the best hiking in New York State. Some favorites nearby include Minnewaska State Park Preserve, with tons of hikes to choose from — among them, the short but scenic hike to Awosting Falls, or the longer trail around a lake at Millbrook Mountain. (Heads up: Minnewaska State Park Preserve does charge a fee, but it’s well worth it.) Further afoot, there’s great hiking in the nearby Catskill Mountains.

Bringing the kiddos? Try Black Creek Preserve, a 2.1 mile walk whose trail crosses a scenic footbridge.

Finally, experience Kingston like never before at A Day Away Kayak, whose affordable rates are a no-brainer for lovers of the outdoors. A quick jaunt up to a waterfall and back takes just over an hour, or spend a few hours out on the water.

Restaurant Kinsley in Kingston, NY offers an inventive New American menu of locally sourced food, designed around the harvest of regional farmers.

Along with artists and other creatives, chefs have flocked Upstate to set up shop in Kingston. Below, some of our favorites.

Each neighborhood seems to have its own little bakery/coffee/sandwich and provisions spot in Kingston, and we’re here for it. In Uptown, this spot is Sissy’s Cafe; in Midtown, find Village Coffee and Goods; and in the Rondout area, check out the very cute Rosie General.

When you eventually tire of gourmet sandwiches, we’re longtime fans of Yum Yum Noodles, for a delicious and indulgent lunchtime noodle bowl, sure to be followed by a nap. Also, blink twice and you might miss Top Taste – but this Jamaican takeout spot was a James Beard nominee and has been featured in Bon Appetit. Other cultural highlights include Tortilla Taco Bar, where you can pretend you’re at a mezcal bar in Mexico City.

Dinnertime brings another plethora of possibilities. Restaurant Kinsley, housed in a restored 19th-century bank, sets the tone with a refined New American menu built around Hudson Valley farms, all served in one of Uptown’s most beautiful dining rooms. Just down the street, its playful sibling LOLA channels a rock-n-roll spirit with imaginative pizzas, mains, and cocktails, perfect for sharing in an upbeat, stylish space. And in the Rondout, Sorry Charlie carries that family tree into grittier territory — a buzzy pizzeria with inventive pies and what might be the best Caesar salad in the Hudson Valley.

Other notable options include Le Canard Enchainé, a romantic French bistro that transports diners straight to Paris, and Mirador, whose deep wine and sherry list pairs beautifully with inventive tapas, bringing a touch of Seville to the Rondout. Wine bar Chleo is a favorite as well, with a menu that shifts constantly to showcase the best seasonal produce cooked over an open fire — grab a bar seat overlooking the kitchen if you can. And in Midtown, Eliza rounds out the mix as a neighborhood bistro inspired by Europe but rooted in the Hudson Valley, serving unpretentious fare in a warm, stylish space from the team behind neighboring Ollie’s Pizza.

As far as nightlife goes, there’s a lot of great bars in Kingston, each with a different ambiance. Beautiful spots like Brunette Wine Bar and Stockade Tavern are perfect for an intimate date night or small gathering, whereas Kingston Standard Brewing Co., West Kill Supply, and Tubby’s – who books outstanding musical talent – are more casual vibes, complete with pub fare. Last, no trip to Kingston would be complete without a visit to Rough Draft Bar & Books, a bookstore and bar (serving some light foods), to do some shopping, or grab a beer and rub elbows with locals for fun events like trivia night.

Hotel Kinsley’s Wall St Suite is a loft-like space featuring original ornate moldings, king bed, full living/seating area, and a marble tile bathroom with a walk-in rain shower and luxurious oversized soaking tub.

Anchored by deep history and brimming with new creative energy, Kingston offers a distinct blend of past and present, where cozy restaurants meet airy natural wine bars, and antique shops share blocks with design studios and artist-run galleries. Divided into three walkable neighborhoods – Uptown, Midtown, and the Rondout – each has its own rhythm, from the painted facades and vintage storefronts of the Stockade District to Midtown’s creative edge and the charming waterfront of the Rondout. Hike in the Catskills by day, kayak the creek by afternoon, and close out with dinner in a reimagined bank or small-plates spot that wouldn’t be out of place in the city.

A few favorites:

• Hutton Brickyards, a sprawling riverside retreat with private cabins and uninterrupted Hudson River views;
• Hotel Kinsley, a thoughtfully restored multi-building property in the heart of Uptown with elevated design and a standout restaurant;
• Kingston Carriage House, a historic property reimagined with modern design, offering an intimate stay steps from the Rondout waterfront, where cobblestone streets, galleries, and restaurants capture Kingston’s creative spirit;
• Glasco BLCK Creek, a thoughtfully designed lakefront estate on 164 private acres, with multiple modern homes, a spring-fed lake, and plenty of space to gather and unwind.

For more options, browse the Hudson Valley Collection in the Escape Club app to explore our favorite design-forward stays – from walkable boutique hotels to private waterfront rentals.