A trip to the Urban Cowboy Lodge doesn’t start when you pull up the winding driveway to the 28-room wooded and red-roofed buildings perched on the hillside like Cardinal at attention. It starts two and half hours earlier (if you’re lucky)– maybe three and a half (if you’re not) when you push play on the Urban Cowboy “pre-arrival” playlist, and begin the game of life-sized tetris that is driving through the Bronx, over the GW Bridge, and, finally, onto the open roads heading north.

After being subliminally prepped to unwind by the musical and literal journey, you arrive, get your welcome drink (bubbles or bourbon), and go to your room. In this way, the arrival represents the whole experience. It begins before it begins, and it lingers long after it’s ended, each step along the way casual but well thought out.

Big Indian Wilderness is exactly what it sounds like. Big. And wild. But there are surprising spots to eat and drink and hike sprinkled throughout. The Lodge which opened in the spring of 2020 (just in time for Covid), is quickly becoming the epicenter of BIW.

The signature of all Urban Cowboy locations is the design by founder Lyon Porter — in this case, decadent mountain luxury, patterns on patterns on patterns, rooms dripping with layers of funky wallpaper, rugs, robes, and blankets. And of course, clawfoot bathtubs: twelve rooms at the Lodge feature bathtubs in the bedroom, and three have outdoor cedar soaking tubs on the patio. Ritualistic bathing has become a central part of the Cowboy’s ethos and we love it.

Clawfoot soaker with a view at Urban Cowboy Lodge Catskills.

Somewhat more subtle but just as definitive as the design is the unique style of hospitality the Cowboy offers. It’s kind of like going to your friend’s house — if your friend’s house was a giant hotel on 70 acres with leather bean bags, a vintage shop, a sprawling deck, an art gallery, a private theatre for two, an insane record collection and a really good restaurant. 

The menu at the Public House at the Lodge, Urban Cowboy’s food program across locations, has small plates to share and big plates to hoard to yourself, or visa-versa. (I know it sounds crazy, but try the cabbage. It’s amazing.)

Every Friday, DJ Billy Joel picks through the Cowboy’s wall of deep cuts, playing mostly funk and soul classics while guests, locals, and randoms eat, drink, and bop their heads. On Saturday, well into living your Catskills best-life, it’s time for Reggae Bingo, or Hip-Hop Bingo, depending on what kind of music is playing. (It’s mostly just bingo with good music, but it’s fun as hell.) DJ Billy Joel from Friday night has now transformed into the bingo host on Saturday, calling out balls, razzing guests, and sprinkling in trivia based on whatever song is playing. 

And this is when the Cowboy is most the Cowboy, people who didn’t know one another the day before are now just a single group of human beings doing something together, in this case, bingo, laughing, getting secretly competitive as the game goes on and tension builds. Who will win the free cocktail? The Cowboy’s modo is, “Arrive as Strangers. Leave as Friends.” And that transformation happens most-easily at bingo every Saturday night.

The out-and-back trail at Giant Ledge is 3.2 miles and well worth the climb.

Though we’re talking a lot about the lodge, believe it or not, there are other things to do in the Big Indian Wilderness. Two of the best hikes in the Catskills are within a short drive from the Lodge: Giant Ledge (3.2 miles out-and-back, moderately challenging) and Slide Mountain (6.2 miles, more challenging). Pick your degree of difficulty and head into the wild. For those willing to try something really adventurous, we’d highly recommend beginning before dawn to watch the sunrise at Giant Ledge; it’s East-facing views are spectacular. Feeling less motivated? The Lodge has trails on property as well, for a perfectly mellow 15-minute walk in the woods.

After the healthy start to your day, it’s time to pack on some calories. The property at the base of the Lodge, Slide Mountain Inn, has BBQ and beers and a functioning 150 year old two-lane bowling alley and arcade in the bar. It’s legit. “Spend Johnny’s cash, hitch another ride.”

If you want to venture further, the Phoenicia Diner, twenty minutes from the Lodge, is a staple for locals and visitors alike, located right on Route 28, quickly becoming the L Train of the Catskills, connecting Kingston to Woodstock to Bovina like Union Square to Williamsburg to Bushwick, the Diner looks like, well, a diner. You can’t miss it.

Visit the beloved Kingston, NY bar/restaurant Lis pop-up at West Kill Brewing.

After the Diner, head to West Kill Brewery for a beer, more nice drives past churches and pastures, more views, and more food. The Brewery has beloved Kingston bar/restaurant LIS running a pop up tent; get a beer, a kielbasa and a bowl of majadera with the fried onions on top, sit in the sun and be happy.

After (or instead of) the Brewery, go to the Pines for some live music, and more food, of course, and maybe one more drink, or two. The nice thing about Slide Mountain Inn and West Kill and The Pines, unlike the Lodge, is that the owners are from the area. Long time locals and recent arrivers blend as the various waves of people escaping New York for the Catskills over the years continue to mix — the rugged mountain hippies, the hunters, the artists, and New Yorkers who came in the two most prominent exoduses from the city, after 9/11 and, most recently, Covid.

If you want to skip the hikes and the drinking altogether, sleep in and head the opposite direction on 28 to Margaretville. Funky cafes and shops selling art, incense, plants, and home decor you won’t find anywhere else line the short main street. The town is having a moment, as they say, and is quickly becoming a destination. Stop by Le Petite Marche — it’s one of our favorites, and then Bun and Cone for some greasy spoon diner food and a soft serve dessert.

And this, if you squeeze it all in, is a pretty perfect weekend upstate. There is not a corresponding return-to-the-city playlist, unfortunately. We suppose you could play the arrival playlist in reverse? But maybe that’s on purpose. Maybe they don’t want the experience to end. Maybe it doesn’t. Maybe it stays with you, a little bit at least. Remember. It begins before it begins. And it lingers long after it’s over.