One Night in a Five-Star Resort at the Center of Big Sky’s Transformation

Welcome to One Night In, a series about staying in the most unparalleled places available to rest your head.

At around 2.2 million acres, Yellowstone National Park is vast—which makes visiting it a big trip to plan, logistically. Figuring out where everything is, what to see, and where to stay to best accommodate the latter requires some careful perusing of many sample blog itineraries, and mapping of routes between spots. I suppose if you have an RV and book campsites ahead you can wing more of it than if you’re just driving, but for those that want a pleasant experience, it’s best to be prepared.

I learned this when I—fairly last minute, for Yellowstone at least, in that people often plan their trips there a year in advance—decided to organize a road trip there since we would "be in the area"—aka Colorado, a day’s drive away from the actual park. I had already been to many of Colorado’s national parks and always wanted to see Yellowstone, so why not make it work? I quickly learned that in-park and nearby accommodations book up quickly—though you can be on the lookout for cancellations, which happen fairly frequently—especially for the most desirable and/or affordable properties. It was during this research that I realized that an actually not crazy choice for my visit would be to stay not in the park, or in West Yellowstone (the most popular town base for those visiting) but in Big Sky, Montana, just a couple short hours away from some of the central Yellowstone sites (again, out there, that’s close).

One of the most touted new properties in Big Sky is the aptly named Montage Big Sky, part of the newer offerings from luxury hotel management brand Montage International. Opened in 2021, the hotel is spotless, and on several "Where to Stay in Yellowstone" lists featuring high-end properties. So after receiving a press release about the property, and realizing I would be in the area during my fall road trip, I reached out to the team to see if I could arrange a stay to see what, exactly, was going on in Big Sky. My couple days there gave me a quiet, up-close look at what major development has meant for this formerly sleepy town.

Tuesday

4 p.m.: After a day seeing Yellowstone’s many sites (and sights)—Old Faithful, the Grand Prismatic Spring, and the Grand Canyon of Yellowstone, among others—we drive through the town of West Yellowstone—kitschy and fun—and along 191, which crisscrosses back and forth between Montana and Wyoming, along the Gallatin River. I’d been warned of the construction going on near the hotel by looking at some the Tripadvisor reviews, but was curious to see exactly what that entailed up close. Indeed, this town, and mountain, are fully in the midst of a massive development project, a process intended to be completed in 2025. The view out of the front of the hotel is of the residential, purchasable apartments being built up (the Montage is part hotel, part luxury residences; the residences cost between $1.5 and 2.5 million). Everything is brand new—the roads newly paved, the vacation houses you drive past look like they just sprang out of the ground.

Long known as a laid back, quiet place to go skiing, a "real" skier’s dream, Big Sky is in the middle of a big shift, and the many parties at play in that shift speak to the money tied up there. The Montage, for example, is owned by the Lone Mountain Land Company, which is part of CrossHarbor Capital Partners, a Boston-based private equity company, and also owns the nearby Spanish Peaks Mountain Club, another luxury residential property. Meanwhile, Big Sky the mountain, owned and managed by Boyne Resorts—originally founded by ski visionary Everett Kircher, and a huge player in the ski resort game—is accessible from these various properties, as they are all literally ski-in, ski-out.

And the Big Sky 2025 plan has gotten plenty of attention. First announced in 2016, as Bloomberg reported, Boyne "unveiled a 10-year, $150 million capital investment plan to transform not just the resort but also the small mountain community bearing the same name from a remote outpost to a full-fledged luxury destination." Indeed, "Some expect the Montage to shift the energy of Big Sky from an unpretentious ski town to a luxury paradise complete with rising real estate costs and significant outside investment," reported Forbes last year.

I’m not much of a skier—to put it bluntly, it makes me crave death—so spending time there in the cuspy fall season was perfect for me. To my surprise, because I’m here as press, upon arrival, we’re given a full itinerary for the next two days. Our room is a suite, overlooking the Spanish Peaks, with a small sitting room with a fireplace and a spread of welcome snacks; had we been paying for it, it would have cost over $1,000 a night. Walking through to the bedroom, the other side of the fireplace is also on, next to a large closet. There are not one but two bathrooms, the larger of which features beautiful marble, a deep sunken tub, and some unique fixtures that I immediately take a photo of to go in my "would love to replicate this later" folder. Indeed, design for the property was done by BraytonHughes Design Studios, out of San Francisco, who were also responsible for the famed nearby Yellowstone Club. But I don’t linger long: I head down to the heated outdoor pool, which is almost empty, and swim a few lengths in peace.

6 p.m. Dinner has been scheduled for us at the Italian restaurant Cortina. (Later, we’re told the owner grew up skiing in Italy, hence the name.) Sans a loudmouth Trump supporter at the table next to us trying to impress his friends with his brushes with our esteemed former president—Marla Maples is mentioned—it is superb, and the space beautiful, with large marble counters and an impressive wine menu, as well as a very knowledgeable waitstaff on said wine menu. I have the veal—delicious. When I go to the bathroom, I see there’s a Toto toilet; class all the way.

8 p.m.: We’re exhausted from many hours of scenic driving, so we hit the Chrome cast and watch Love Is Blind. I have a very comfortable king bed at home, but there is truly nothing like a hotel king.

Wednesday 

8 a.m.: We grab breakfast at the cafe, which is a walkthrough space near the main lobby—the pastries are unreal—before meeting our hiking guide, who takes us to Ousel Falls, a popular local hike. He tells us about all the nearby flora and fauna, and also about sharing a townhouse that’s owned by the hotel with a group of other friends who all work for the hotel—a reality show in the making! We talk a bit about grizzly maulings, and the complex businesses that own all this land and property now.

Affordable housing is, as ever, an issue in this area, particularly given the grand aspirations had for it and subsequent astronomic growth. "Even more modest sales and rentals are soaring, making it harder for both visitors and the local workforce to find affordable lodging," the New York Times reported last year. "Big Sky is trying to alleviate the pressure for its staff by building more employee housing, and it currently can house 700 workers (there are about 1,700 employees)." Our guide mentions there are currently limited stores in town—basically one for each thing you’d need—which makes groceries expensive. Many residents, he says, drive the hour-ish to Bozeman to pick up what they need when they can, though, he says, more stores are being built to rectify this issue.

12 p.m.: I read a bit on the veranda looking out over the mountains; while I do, I notice a woman whose job appears to be carefully touching up the building’s interior wood grain. It is mesmerizing.

1 p.m.: Lunch is at the poolside cafe, Backcast—which is, again, way better than it has any right to be. It’s just us and another couple, and we chow down on spicy, buttery shrimp and guacamole. Then I head to the 10,000-square-foot spa—which features the only nail salon in Big Sky—where I get an hour-and-a-half-long massage that sets me right again. After, I spend some time in the (empty) interior pool and sauna, which is surrounded by a wall of what appears to be volcanic rock. Everything is stunning, brand new, and deeply peaceful, in the general muted spa tones of grays and whites—it’s hard to imagine that in the summer and winter, this place is likely crawling with people.

5 p.m.: We have some drinks at Alpenglow, the bar in the lobby with, like every other space in the hotel, views of the mountains beyond. Then we head down to the Beartooth, a bowling alley and bar on the hotel’s lower level. Our bartender tells us a bit about how he ended up here—everyone seems to be a huge nature lover/skier/hiker/etc—as we chow down on burgers and fries. After losing at both pool and bowling, I call it a night and head to sleep—we have a big morning ahead of us.

Thursday

7 a.m.: We’re up early because the hotel has arranged a fly fishing lesson for us on the Gallatin, with Gallatin River Guides, which my partner is excited about, and I’m excited but slightly nervous for. (He went horseback riding for me on the prior leg of this trip, this is his treat.) We pack up all our stuff, and grab some stunningly packaged—in mason jars—salads for later at the cafe. Though I’m obsessed with the waterproof gear they give us, for the first hour or so on the river, my feet are fully freezing off, given that it’s like 30 degrees out. Our guide distracts me by telling how he got into fishing and hunting. Once we wander downstream into the sun, I’m enjoying myself more, and catch not one but two trout. (It’s catch and release; as our guide points out, these fish are his business partners.) When we get back to the shop, I reward myself with a Gallatin River Guides T-shirt.

11 a.m.: As we leave town, and head north to drive through Bozeman to the north entrance of Yellowstone (all the better to see more wildlife) I think back to the literally dozens of trucks we’d seen heading up the hill as we drove down to the river, all presumably busy getting the 2025 plan to where it needs to go. It’s unique to be able to visit a place as it’s in the middle of such a stark evolution, and I’m left even more curious than when I started about what Big Sky will look like in just a few more years.

This essay is part of a three-story mini-series from executive editor Kate Dries’s fall road trip through the West. Previously, a college-run hotel in Grand Junction, Colorado, and a luxury dude ranch in Wyoming.

Top image courtesy of Montage Big Sky

Related Reading:

A Rambling Fishing Retreat in Montana Cuts Through Cabin Conventions

The Italian Huts Where Mountaineering Was Born