The Perfect Three-Day Weekend in the Catskills

I recently spent a long weekend in the Lower Catskills—Livingston Manor, Narrowsburg, Callicoon, Roscoe—a mere two an a half hour drive from New York City. It might have been the complete lack of Wi-Fi, TV, and cell service (most of the time), but I broke in to Monday with a new level of refreshed focus. Not only can you count on stunning views—we’re talking trees as far as the eye can see—but there are plenty of amazing food options, incredibly interesting locals to meet, and lots of other exciting attractions.

Ahead, my attempt to spread the joy that is a three-day weekend exploring a handful of towns during a vacation in the Catskills. Read on and start planning that trip. Step one: find a car fit for the drive—preferably one with a killer sound system. Looking for a suggestion? We took a Lincoln Black Label MKX, which comes equipped with 19 speakers, i.e., it was practically made for road-tripping.

The Arnold House is a rustic home located in Livingston Manor, a town in the southwestern tip of New York state. For the sake of keeping this a three-day weekend (we could spend a week exploring the Catskills!), we’ll call this home base. If you’re looking for an inn with amazing food and regular live music sessions in a barn with a bonfire burning out front, this is your spot—the owners will treat you like family. On a recent trip, we rented the lake house owned by those fine people at the Arnold House. Located right on Shandelee Lake, this was the perfect spot for all four of us to sprawl out and truly take a mental break from the hustle and bustle of New York City. The home is a mix of modern elements and throwback features from the 1950s. Our favorite part: a vintage cooking space with a stovetop that pulled out from underneath the ovens (a Frigidaire Flair, for those well-versed in vintage accessories) and an Eames lounge chair to enjoy in the living room.

The same people behind the Arnold House own two other properties—the North Branch Inn (which we’ll revisit later for dinner) and the recently opened 9 River Road, in the nearby city of Callicoon. The area isn’t quite known for its abundance of inns and hotels, so if you’re looking to rent a home, head to Airbnb—there are never-ending options of quaint, modern, and cozy homes.

Day One

The Catskills area is known for its throwback diners—try to hit up a different one each morning. “World Famous” Roscoe Diner is the perfect place to start. The menu is a refreshing mix of breakfast-all-day options and giant sandwiches; basically everything there is to love about a breakfast stop.

Driving in the Catskills is far from a burden—the stunning expanses of mountain views make any jaunt a welcome break from day-to-day life. Drive 40 minutes south of Roscoe to Narrowsburg. There you’ll find a handful of local boutiques, including Madame Fortuna (a local jewelry maker), Dyeberry Weavers (don’t forget to ask about the loom in the back of the store!), and One Grand Books, an entire shop curated by celebrities answering the question: which books would you bring with you to a deserted island? Spend the afternoon getting to know the many locals who make up Narrowsburg’s shopping district.

If dining with an uninterrupted view of the Delaware River sounds like your kind of situation, head to The Heron, then grab your swimsuit—Narrowsburg is a great spot to spend some time river tubing. There are two options: a relaxing five-hour float down the Delaware, or tubing through the rapids at Skinners Falls. Depending on your schedule, give both a try.

The North Branch Inn Restaurant & Bar Room serves an incredible seasonal menu that’s constantly changing. We tried the cheese and charcuterie plate (which comes with a side of preserves and honey butter), the “Cow” entrée option (New York strip with potato confit, garlic, and baby leek), and the “Vegetarian” option (spinach and garlic fettuccine with leek, egg yolk, pesto, and zucchini). Definitely don’t miss dessert.

Day Two

If you’re staying in a house, as we did, take some time to make your own breakfast. There’s nothing better than actually having the time to make all of your morning favorites without having to worry about getting to work. If you are looking to get out, hit up another breakfast spot, like Robin Hood Diner near Livingston Manor.

You can’t spend a weekend in the Catskills without getting some quality time in the Great Outdoors. This part of New York is full of gorgeous hiking trails. Stop by Main Street Farm in Livingston Manor to grab sandwiches and other lunch provisions, then take a few hours and explore Giant Ledge Mountain, which is known to have some of the best views of the Catskills. The entire hike is just over three miles (about two hours of walking). If you’re looking for something a bit longer, keep hiking to Panther Mountain (about seven miles, or four hours).

Clean up from your hike and head to the Catskills Brewery for a flight (or two). We recommend the Ball Lightning Pilsner, Freak Tractor, and Darbee’s Irresistible Pale Ale. Bring home a growler of your favorite.

The Rolling River Café is the perfect place to relax after a long day of hiking (and drinking). Located on the Little Beaverkill River, this farm-to-table spot changes its menu weekly to keep up with the freshest ingredients from the region. Eat in the renovated carriage house—which features a revolving display of local art—or enjoy your meal next to the babbling river.

Whether you make your own (if you’re renting a home) or just curl up near a fireplace at one of the area’s bars, restaurants, or inns, take some time by the fire to tell stories or set up a game of Scrabble. If there’s only one or two of you, get to know some of the locals and ask them to join in.

Day Three

Grab a few pastries at Bradenburg Bakery—think strawberry-rhubarb torte, warm scones, crisp danishes. This tiny shop is designed with old-school Vienna in mind, making it a great Instagram op, as well.

After fueling up, hop on over to the Callicoon Farmers’ Market. It’s not huge by any means, but you’ll find fresh vegetables, just-baked bread, handmade soaps, delicious preserves, and local art, as well. Be warned: there are no dogs allowed at this market.

Matthew’s On Main is a favorite lunch spot for locals. There’s a solid mix of American food and seasonal specials to get anyone through the afternoon. Hit up Callicoon Creamery for a sweet treat to follow lunch. We tried the brownie sundae—it’s not to be missed. Take a leisurely drive through Youngsville, Jeffersonville, Callicoon, and Callicoon Center to fill the afternoon—and make sure to stop and take in the scenery (and shops!). The entire loop is about 34 miles round-trip and will take you about an hour. Plan your route on Google Maps before heading out for simple navigation.

The Tavern at the Arnold House is a great spot for a quick dinner. We went on a Saturday and caught some live music in the adjacent barn after dinner. Speaking of which, try the chicken sandwich—one of my travel buddies described it as one of the best he’s ever had.

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