Ask a bunch of people what they love about the Hudson Valley, and you’ll get wildly different answers each time. Indeed, such is the beauty and diversity of this lush and lively destination — just a few hours north of New York City — that everyone from thrill-seekers and foodies to history junkies and shopping enthusiasts can pack a long weekend with memorable experiences.
Get lost in the hip cities or take in the grandeur of the Catskill Mountains. Dine at some of the most well-regarded farm-to-table restaurants in the state or go treasure hunting at innumerable antiques shops. Drink at distilleries and cideries or pick fruit and veggies at the sweeping orchards.
The always-evolving Hudson Valley has all this and more — enough to convince the first-time weekender to come back soon for another, longer visit. To start, here’s a weekendlong tour of the region even repeat visitors will love.
As always, check for travel guidelines and closures before planning your trip.
Friday: Wander the Culture-Packed City of Hudson
Your introduction to the region will be in its namesake town: Hudson. Settle in for a rib-sticking breakfast at the nationally recognized Cafe Mutton. For a sweet start, grab the crepes, or for something savory, try the innovative porridge with mutton and a poached egg. Afterward, head to the stretch of Warren Street between South Seventh and South First streets — it’s the life force of the downtown neighborhood and a must-stop when you’re in town.
Warren Street is a mile long and lined on either side with galleries, antiques stores, clothing boutiques and places to eat and drink. There’s no pressing need to chart your course, as your interests will pull you into one shop or another, but do look out for the Spotty Dog Books & Ale for — you guessed it — reads and pints; FINCH Hudson for modern home and garden goods; and Florent for exquisite house-made perfumes.
When you get hungry again, dip into Grazin’, a modern diner with a farm-to-table ethos that’s known for its wide array of grass-fed Angus beef burgers.
After lunch, stop to admire the mansions and town houses that line the streets surrounding Warren, showcasing architectural designs from nearly every major American period, including Federal, Victorian and early Arts and Crafts. Pause for coffee at WYLDE Hudson, which also sells clothing, books and objects for the home — and wine, as well, if you’re in the mood. MOTO Coffee Machine, where you can also ogle the motorcycles, is another good choice, as is Verdigris Tea & Chocolate for one of New York’s finest hot chocolates.
Come dinnertime, you can pretty much go anywhere for a stellar meal. But some of Hudson’s more celebrated spots are Lil’ Deb’s Oasis for tropical-style comfort food and the funky Backbar for Southeast Asian small plates.
Saturday: Explore the Valley’s Natural Wonders
After filling up on hearty omelets and breakfast sandwiches at the Wick Restaurant, a bright, airy café in Hudson, it’s time to immerse yourself in the natural beauty of the surrounding valley. A hike inside the bucolic Greenport conservation area, which is only a six-minute drive from Hudson, is your first activity of the day. Lose yourself in eight miles of trails, from easy to challenging — many with painterly views of the Hudson River and Catskill Mountains.
To refuel, take a quick trip north to the charming town of Chatham in Columbia County. You’ll love the Americana vibes at Main Street Goodness, but the menu is far from typical: Try the Tuscan omelet (sun-dried tomato, asparagus, Parmesan and house-made herb oil) or the turkey Reuben on thick-cut marble rye. Don’t leave without swinging by the Chatham Bookstore to pick up a new weekend read — it has one of the best book collections in the Hudson Valley.
From there, it’s an easy 10-minute drive to Art Omi, a 120-acre sculpture and architecture park with more than 60 pieces scattered throughout the manicured grounds and walking paths. Check out the park’s website if you want to chart a route, or just let yourself be surprised by what’s around the corner.
Head back into Hudson for dinner at Feast & Floret for Tuscan-accented Italian and some of the Hudson Valley’s best pasta dishes, and end your night with a show at Basilica Hudson. The solar-powered former factory is host to a wide variety of events, like film festivals and intimate music performances.
Sunday: Take a Day Trip to Rhinebeck and Kingston
Part of the allure of the Hudson Valley is how accessible its cities and towns are from each other. On your last day in the area, take a quick drive on the Taconic State Parkway to the towns of Rhinebeck and Kingston. On your way, stop for breakfast at West Taghkanic Diner, a retro-style spot serving cheffed-up takes on classic dishes. Don’t leave without an order of the cornmeal-buttermilk pancakes — they’re impossibly fluffy.
One of the top reasons to hit Rhinebeck on a Sunday is the Rhinebeck Farmers’ Market, which runs from approximately May through December. It’s one of the area’s finest, with everything from fresh fruit and veggies to homemade pies, dumplings and breads.
But even if you come during the colder months, the town’s main intersection (East and West Market streets, and Montgomery and Mill streets) is worth exploring. You’ll find a variety of unique boutiques and vintage clothing shops, interior-design meccas (Hammertown, for one, will have you wanting to redo your entire home) and farm-to-table restaurants. For a sugar rush, try one of the most popular hangouts in town, the celebrity-owned Samuel’s Sweet Shop.
Now it’s time to cross the Hudson River to explore Kingston, a trendy, ever-evolving city that’s only a 20-minute drive away. The town is bookended by two lively neighborhoods: the Rondout (or Waterfront District) and Uptown (or Stockade District). The easiest way to get between the two is to drive, but that doesn’t take long.
Start with a stroll along the waterfront in Rondout. Then work your way up Broadway to check out boutiques like Clove & Creek for home goods, Milne Antiques & Design for modern and industrial pieces and Hops Petunia Floral for flowers, jewelry and kitchenware.
Cap off the weekend with dinner in Uptown Kingston, where you’ll be spoiled for choice. Lola Pizza, with its famed Tiger Paw pie made with pepperoni and hot honey, is a favorite. Or for a trip to the Caribbean in upstate New York, stop in Midtown Kingston (located between the Rondout and Uptown) and visit tiny Top Taste, a no-frills Jamaican spot beloved for its curried goat, oxtail and other authentic fare.
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