Years ago, Escape Brooklyn first created a guide to Kingston, NY inspired by a trip to its downtown area. Retail pioneers Kingston Wine Co. had just opened shop there, with a handful of others including Milne, Hops Petunia, Brunette Wine Bar, and Clove & Creek. Nowadays, the “downtown” area of Roundout is still alive and well, with its own handful of new shops and boutiques; but for this updated guide, we’re setting our sights “uptown,” to Kingston’s historic Stockade District.
An eight-block radius encompasses the Stockade District, the oldest section in New York’s oldest city. The neighborhood dates back to the 1700s, and original historic details can still be seen everywhere on the buildings from the inside out. Not long ago, many of these buildings were vacant; but thanks to an influx of creatives and entrepreneurs, nearly every storefront in the Stockade District is now filled, drawn in by Kingston’s small-town charm, history, tight-knit community, and proximity to the Catskills.
We thought the holidays would be the perfect time to put out an additional guide to Kingston… Because as long as you have to buy gifts for everyone else, you might as well make a weekend of it!
At 100 miles from NYC, the best way to get here is definitely car rental, though Kingston is accessible by Trailways bus and walkable when sticking to certain neighborhoods. Read on for an outline of some of our favorite shops, followed by all the details you need to round out a trip here, including lodging and dining recommendations.
For the Man in Your Life: Located in the heart of the Kingston Stockade district, Hamilton & Adams was just awarded the best menswear shop in the Hudson Valley. It’s stocked with a great selection of mens apparel — think United by Blue, Raleigh denim, Grayers, and Faherty — but it also has gifty stuff for all, including books, cold weather gear by Upstate Stock, grooming products by Hudson Made, and more. Additionally, their signature line of Upstate & Chill products are great for second homeowners, recent transplants, or just anyone who loves Upstate.
For the Ladies: Neighboring boutiques Oak 42 and Flora Beauty are very complimentary: one carries womens apparel, and the other is a wellness destination & apothecary. Created in 2015, Oak 42 was born of necessity as NYC expat Christen Drexler returned to her hometown and noticed a serious need for modern, fashionable clothing for women. She stepped in, opening her boutique stocked with cool and affordable women’s clothing and accessories. Next door to Oak 42, Flora Beauty is an apothecary and spa, stocked with artisan perfumes, oils, sprays, and other grooming products. Its services include acupuncture, facials, massages and more.
Around the corner, Rebecca Peacock has created a beautiful shop not only as a showcase for her own creations; it also serves as a gallery for some of her other favorite regional artists. Rebecca’s gorgeous handmade jewelry is made in a farmhouse overlooking a creek, with top quality semi-precious gemstones, diamonds, and 14/18 karat gold. Across the street from Rebecca, don’t miss Anderst, where Scandinavian and Catskills sensibilities combine to create a literally perfect shop carrying womens apparel, vintage/antiques, accessories, and art. You can stock up on CBD products here, too!
For the Geek Who Drinks: …or you just know one, Rough Draft books & bar is our absolute favorite new place in Kingston. Whether you need a coffee, a beer, or a book, this place has you covered. Their trivia night on Thursday is legendary; according to locals, it clears out all the other bars in town!
For the Aspiring Cook, Master Chef, and Every Level Between: Whether you’re shopping for a pro, or a total newbie, you’ll find exactly what you need to cook up delicious and inspiring meals at Blue Cashew. Their collection at the shop ranges from knives to appliances, and cook books to actual cooking classes. In the rear of the store, the space opens into a large kitchen, which regularly hosts cooking classes by award-winning chefs. We love the idea of a cooking class as a holiday gift — is there anything better than gifting an experience?
Vintage Lovers, Rejoice!: There is SO much good vintage in Kingston — both apparel and home furnishings. Lovefield Vintage should be any vintage lovers first stop, with its beautiful and affordable collection of clothing and accessories. For vintage home goods, dig around at antique shop Kingston Consignments, or go straight for the good stuff at mid-century modern boutique Stuff.
Find Something For Anyone: Got a big shopping list this year? Check everyone off your list in shops like Exit Nineteen, where there’s something for literally everyone: kids, teachers, your boyfriend, and your kooky aunt. Owners John Krenek and Jamie Niblock opened their first Upstate location 10+ years ago after leaving the NYC for the village of High Falls, receiving praise from the likes of Interior Design Magazine, Elle Decor, and New York Home. Their new location in Kingston offers a mix of new and vintage, where gifts for all are mixed amongst vignettes of home decor for cozy cabins, modern homes, and everything in between.
Where to Eat, Drink, and Stay in Kingston
Since its award as best Best B&B Breakfast in the Hudson Valley, we’ve been eager to try out the Forsyth. Branding itself as “the perfect home base for the modern explorer,” the four-room B&B is located in Kingston’s Roundout area just a few blocks from the Hudson River. Each charming room in the house has original brick walls, exposed beams and cozy nooks; or stay in the event barn, with a lofted bedroom and plenty of room to spread out. The highlight is breakfast, where owner/French Culinary Institute-trained chef Tamara feeds her guests a three-course meal to write home about. And though dining alone is nice, we recommend you plan your mealtime with other guests to socialize with your fellow Upstate explorers.
On the subject of food, there’s a handful of new restaurants and bars in Kingston since our last guide. Wilde Beest has perhaps made the largest splash; it’s seasonally changing menu has found its perfect home in a beautiful space in the heart of the Stockade district. Although the menu also explores fields and forests, locals agree that the the highlight is the seafood — and we agree. Try the scallops! For something more casual, Kovo Rotisserie is also delicious, open for lunch, brunch, and dinner.
With all this exploring and shopping, you’ll definitely need to squeeze in a strong drink at the end of the day. Newly opened and still somewhat under the radar, we just discovered The Crown, a cocktail bar housed in Kingston’s oldest home, dating back to the 17th century. Comprised of five distinct rooms/environments, the interior is inspired by Parisian lounges and speakeasies, and spans two floors. Check it out for their awesome happy hour, live jazz/performance nights, or fireside for a nightcap. Last, Kingston’s newest arrival on the bar scene is amongst its best at Lis, serving up Polish comfort food (think pierogies, kielbasa, and Polish flatbread) and delicious, inventive cocktails. Arrive on the early side to grab a seat by the wood stove!
