In the mood for food and adventure? Cruise to these destinations for day trips in the Sullivan and Ulster Catskills.
The Catskills are calling! For foodies in need of an escape, there’s nothing quite as wonderful as a day trip around the picturesque Sullivan and Ulster counties. Not only are the regions stocked with sights to see and things to do, but they’re also packed to the brim with some of the most mouthwatering eats in the Hudson Valley.
So what are you waiting for? Check out these day trip itineraries, then get ready for a food-filled day in the Catskills.
Monticello – Livingston Manor – Callicoon
If natural beauty is what you seek, look no further than Sullivan County. Weekend trips to the Sullivan Catskills are all about savoring the great outdoors, exploring hidden gems, and discovering delightful dining throughout the region. Whether you’re doing a quick cruise up from Orange County or driving north from New York City, you’ll love exploring these destinations.
Play: If Monticello rings a bell, that’s probably because you’ve heard it mentioned as the home of Resorts World Catskills. The casino sits right down the road from The Kartrite Resort & Indoor Waterpark, a family-friendly hub filled with fun galore.
Eat: With so much to do in one area, it’s hardly a surprise that there are a fair number of places to eat as well. If Americana cuisine is what you crave, head to Bixby’s Derby inside The Kartrite. Nearby at Resorts World, Lotus is a hotspot for Asian eats in an elegant setting, while Scott Conant’s Cellaio celebrates the flavors of Italy.
Stay: With so much to do between the two resorts, why not stay the night? Families will adore the spacious, kid-friendly rooms at The Kartrite, while couples and friends will enjoy the happening vibes at Resorts World Catskills.
Play: Livingston Manor has fast garnered a reputation as the Brooklyn of the Catskills, and for good reason. With an abundance of Instagrammable storefronts scattered around Main Street, this town is a shoppable delight. Find your next treasure at Jitterbug with records, art, and kid’s games, or Life Repurposed—a trove of thrifted finds. For knickknacks and gifts, pretty much everyone will fall head over heels at DROOZ and Company. And the curated bookshop, One Grand, will leave you wanting to browse the shelves for hours.
Eat: One of the hardest parts of dining in Livingston Manor is deciding where not to go. If an a.m. bite is what you seek, look no further than Main Street Farm, offering delicious breakfast sandwiches and coffee (with a lunch menu, too). When the dinner hour rolls around, make a beeline to The Arnold House for an elegant, welcoming interior and a menu that will make your mouth water. Smoked trout rillette? You can find it at the Catskill Food Truck at Catskill Brewery. Then, try a glass of natural wine at Sunshine Colony, or take in the view at Upward Brewing Company and sip the Base Camp LagerBier, a 2023 World Beer Cup winner!
Stay: If you fall in love with the Catskills town, turn your day trip into a weekend away with an overnight at The Arnold House. Here, guests can choose between 16 different types of rooms, all of which feel cozy, fresh, and welcoming.
Play: A short drive away from Livingston Manor, Callicoon is the epitome of small-town charm in the Catskills. During a visit, catch a flick at The Callicoon Theater, then shop in style at Spruce Home Goods and Litt Home & Book. Storefronts line the streets, so there’s no shortage of browsing here.
Eat: Just a short jaunt outside of the town’s center, Seminary Hill Orchard & Cidery is a hub for ciders and scrumptious dishes. A short drive down the road in Kenoza Lake, Kenoza Hall offers lake views and elegant, old world cuisine.
Stay: After a full day of dining and discovery, rest your head at the Bungalows at Kenoza Hall. The 10 luxurious accommodations pay homage to the historic bungalow colonies of the Catskills during the 20th century.
New Paltz – Saugerties – Woodstock
Located along the western bank of the Hudson River, Ulster County has an enviable mix of outdoor recreation, top-tier shopping, and bucket-list dining destinations. With so many iconic sites packed into one county (Mohonk Mountain House, Opus 40, and the Saugerties Lighthouse, anyone?), it’s all too easy to plan day trips in the Catskills region.
Play: As home to SUNY New Paltz, the town embraces the college’s creative spirit with an abundance of shoppable storefronts. Hit up Verde, Eden Boutique, or Rock Candy Vintage for clothes of all styles, then venture into Water Street Market for antiques and giftable goodies galore. If hiking in the Catskills is what you seek, the River-to-Ridge Trail is ideal for bikers, runners, and walkers, with Mohonk Preserve, Minnewaska State Park, and the Empire State Trail all easily accessible as well.
Stay: After a long day in town, treat yourself to an unforgettable overnight stay at Mohonk Mountain House. The historic Victorian lodge offers spectacular views of the Hudson Valley, and the grounds are packed with things to do. With ice skating, hiking, and family-friendly activities all onsite, it’s more than likely you’ll want to make a weekend out of your stay here.
If you want something just outside of New Paltz, look no further than Wildflower Farms, part of the Auberge Resorts Collection. With classes and experiences galore available, the resort is ideal for vacationing in style. Plus, foodies won’t want to miss a meal at Clay, the venue’s farm-to-table restaurant.
Play: Saugerties has so much happening, it’s hard to know where to start. Lovers of arts and culture won’t want to pass up a trip to Opus 40, while outdoor adventurers might want to check out the picturesque Saugerties Lighthouse or the scenic Esopus Bend Nature Preserve. In town, a wealth of boutique clothing and furniture shops await.
Eat: The restaurant scene in Saugerties is so robust that it can be hard to score a table on the weekend if you don’t have a reservation. Do yourself a favor and book a spot at The Dutch for American gastropub fare or meander down the road to The Kitchen at Salt & Fire for local flavors with a wood-fired touch. If you want to dine with a view of the water, look no further than BLACKBARN, the iconic New York City restaurant with an upstate outpost at Diamond Mills.
Stay: Embrace the local B&B scene with a weekend at The Villa at Saugerties, a charming bed and breakfast just outside of the center of town. In warmer weather, The Villa boasts a picture-perfect pool, which is a treat for swimming and lounging on sunny days. Stick around for breakfast in the a.m., which the B&B’s owners lovingly prepare for guests.
Play: Woodstock is fun. Yes, it’s iconic, but it’s also a happening place to be during a weekend in the Hudson Valley. With attractions like the Bearsville Theater and the Woodstock Playhouse for shows, the Mower’s Saturday/Sunday Flea Market for local finds, and the entirety of Tinker Street for shopping, it’s easy to get caught up exploring the town.
Eat: After adventuring in Woodstock, treat yourself to a gourmet meal that will make your taste buds sing. Kick the night off right with drinks at Early Terrible, then get ready for a dinner you’ll dream about. Millstream is a delight for elegant, Americana bites, while Cucina is the place to go if you’re craving upscale Italian. No matter where you end up, don’t skip out on Nancy’s of Woodstock Artisanal Creamery for dessert.
Stay: With treehouse vibes and a prime location in town, Woodstock Way Hotel is an easy choice when it’s time to decide where to spend the night. The hotel is uber-cool, thanks to a modern design and bright and welcoming interior. Plus, did we mention it’s right next to a waterfall?
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