The Ideal Three-Day Getaway in the Catskills

I recently enjoyed an extended weekend in the Lower Catskills—covering Livingston Manor, Narrowsburg, Callicoon, and Roscoe—just a two-and-a-half-hour drive from New York City. Perhaps it was the absence of Wi-Fi, TV, and cell service for most of the time, but I returned from my trip with a newfound clarity and focus. You can expect breathtaking vistas, with trees stretching endlessly, along with a plethora of fantastic dining options, intriguing locals to connect with, and numerous exciting attractions to explore.

Below, I’ll share my journey of joy during a three-day weekend discovering several towns while vacationing in the Catskills. Keep reading to start planning your own adventure. First step: find a car suited for the journey—ideally one with an exceptional sound system. For our trip, we opted for a Lincoln Black Label MKX, which boasts 19 speakers, making it practically perfect for road-tripping.

The Arnold House is a charming rustic retreat situated in Livingston Manor, at the southwestern edge of New York state. To keep our adventure within a three-day weekend (though a week in the Catskills would be delightful!), we’ll make this our home base. If you seek an inn featuring exquisite cuisine and regular live music in a cozy barn with a bonfire out front, look no further—this place feels like family. During a recent visit, we booked the lake house belonging to the wonderful folks at the Arnold House. Nestled right by Shandelee Lake, it was the perfect getaway for the four of us to unwind and escape the fast pace of New York City. The house beautifully blends modern amenities with nostalgic touches from the 1950s. Our favorite feature was the vintage kitchen, complete with a stovetop that slid out from under the ovens (a Frigidaire Flair, for the vintage enthusiasts) and an Eames lounge chair perfect for relaxing in the living room.

The same owners of the Arnold House have two additional properties—the North Branch Inn (which we’ll revisit later for dinner) and the newly opened 9 River Road in nearby Callicoon. The region isn't particularly known for its abundance of inns and hotels, so if you're looking to rent a home, check out Airbnb—there's a plethora of quaint, modern, and cozy homes available.

Day One

The Catskills region is famous for its nostalgic diners—make it a goal to try a different one each morning. Start your day at the “World Famous” Roscoe Diner, where the menu offers a delightful array of all-day breakfast options and oversized sandwiches; it’s everything you could want from a breakfast spot.

Driving through the Catskills is a pleasure, with breathtaking mountain views transforming any trip into a refreshing escape from daily life. Head 40 minutes south of Roscoe to Narrowsburg, where you can explore local boutiques like Madame Fortuna (a local jewelry artisan), Dyeberry Weavers (make sure to inquire about the loom in the back!), and One Grand Books, a unique shop curated by celebrities that answers the question: which books would you take to a deserted island? Spend the afternoon mingling with the friendly locals who contribute to Narrowsburg’s vibrant shopping scene.

For a dining experience with an unobstructed view of the Delaware River, make your way to The Heron, then get your swimsuit ready—Narrowsburg is ideal for some river tubing. You can choose between a leisurely five-hour float down the Delaware or a thrilling ride through the rapids at Skinners Falls. If time allows, try both for the full experience.

The North Branch Inn Restaurant & Bar Room boasts an exceptional seasonal menu that changes frequently. We enjoyed the cheese and charcuterie platter (accompanied by preserves and honey butter), the “Cow” entrée featuring New York strip steak with potato confit, garlic, and baby leeks, and the “Vegetarian” dish of spinach and garlic fettuccine with leeks, egg yolk, pesto, and zucchini. Be sure to save room for dessert.

Day Two

If you're staying in a rental house like we did, take some time to whip up your own breakfast. There's something special about having the freedom to prepare all your morning favorites without the pressure of work. If you prefer dining out, consider visiting the Robin Hood Diner near Livingston Manor for a tasty morning meal.

No weekend in the Catskills is complete without some quality time in the great outdoors. This region is filled with stunning hiking trails. Stop by Main Street Farm in Livingston Manor to pick up sandwiches and other lunch essentials, then spend a few hours exploring Giant Ledge Mountain, famous for its breathtaking views of the Catskills. The hike is a little over three miles, taking about two hours. For a longer adventure, continue on to Panther Mountain, which spans approximately seven miles and takes around four hours.

After freshening up from your hike, head over to Catskills Brewery for a flight (or two) of their craft beers. We recommend trying the Ball Lightning Pilsner, Freak Tractor, and Darbee’s Irresistible Pale Ale. Don’t forget to take home a growler of your favorite brew.

The Rolling River Café is the ideal spot to unwind after a day of hiking and enjoying beers. Situated by the Little Beaverkill River, this farm-to-table restaurant updates its menu weekly based on the freshest local ingredients. You can dine in the renovated carriage house adorned with a rotating selection of local art, or enjoy your meal next to the soothing sounds of the river.

Whether you cook for yourself (if renting a home) or cozy up by a fireplace in one of the area's bars, restaurants, or inns, take some time to share stories or play a game of Scrabble by the fire. If you're with just one or two people, engage with the locals and invite them to join in.

Day Three

Start your day with some delightful pastries from Bradenburg Bakery—think strawberry-rhubarb torte, warm scones, and flaky danishes. This charming little shop captures the essence of old-school Vienna, making it a perfect Instagram spot as well.

Once you've fueled up, make your way to the Callicoon Farmers’ Market. While it's not extensive, you'll discover fresh vegetables, just-baked bread, handmade soaps, delicious preserves, and local art. Just a heads-up: dogs are not permitted at this market.

Matthew’s On Main is a popular lunch destination among locals. They offer a solid selection of American dishes alongside seasonal specials to power you through the afternoon. Afterward, treat yourself at Callicoon Creamery; the brownie sundae we tried is a must-have. Take a scenic drive through Youngsville, Jeffersonville, Callicoon, and Callicoon Center to fill your afternoon, making sure to pause and soak in the beautiful views (and visit the shops!). The entire loop spans about 34 miles round-trip and takes roughly an hour. Use Google Maps to plan your route for easy navigation.

For a quick dinner, head to the Tavern at the Arnold House. We visited on a Saturday and enjoyed live music in the adjacent barn after our meal. And don't miss the chicken sandwich—it received rave reviews from one of my travel companions, who called it one of the best he's ever had.

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