For some reason, that one dude-ranch episode of Modern Family plays over and over again on late-night TV. I won't lie, I'm heavily influenced by what I watch on the tube, and that half-hour of comedy—wherein clay-pigeon rifles are humorously mishandled and an actual triangle chime beckons the guests for a chuck wagon dinner—is part of the reason I wanted to go to the Resort at Paws Up in Greenough, MT, about a 45-minute drive from the Missoula airport. That, and the fact that every magazine editor I know has been seen on Instagram wandering the joint in form-fitting plaid shirts and scuffed-just-so cowboy boots. My FOMO reflex was really acting up.

There is, after all, much to feel envious about, the least of which is Paws Up's sheer amount of land and sky, things city slickers don't realize they need until they've been plunked into 37,000 acres of nothing but. Though the hospitality biz is the main moneymaker here, the ranch, once owned by hall-of-fame aviator Charles Lindbergh, is still a working cattle operation, although there are only a few hundred heads on the whole expanse. (When I was there, I heard nary a moo, but then again, when you've got space of this magnitude, the utter quiet is also something you can't help but notice. Once during my visit, I did, to my amazement, hear the wings of a bald eagle flap in the wind as it flew low before my very eyes.)

Anytime you can text your friends back home a few photos of the 3,258-square-foot "cabin" in the woods you're shacking up in for a few days, do it. Because without proof, they won't believe you. I stayed in Camp Fortunate—the Wilderness Estate (there are 10) located at the top of a forested hill overlooking the ranch below. I had approximately four bedrooms, four bathrooms, two jetted tubs, several fireplaces, and Western accoutrements galore (hide-covered everything, antlers here and there, and peculiar art pieces featuring threadbare denim) to make me feel at home on the range. Two lime-green Kia Souls are parked in each driveway for the guests—from the Wilderness Estates, it's about a five-minute drive to the main post, where Trough, the dining hall, and Tank, the bar, are located. At the other end of shelter spectrum are the Blackfoot River–side en suite glamping tents, which are so luxurious they've got copper tubs at the foot of the four-posters. Something tells me there are Wild West cowboys rolling over in their unmarked graves.

Speaking of Tank and Trough, the food at Paws Up is pretty good for the middle of Montana, in that you can order a beef-and-foie-gras burger with morel mushrooms or avocado-and-heirloom-tomato toast and never feel too far from San Francisco, gastronomically speaking. During their special culinary weekends, the grub gets even better with the addition of guest chefs to the roster. When I was there, stars from the show Top Chef cooked for us; just recently, the country's top grill masters kept the home fires burning. Upcoming, the Bounty on the Blackfoot event in August will feature L.A. chef Brooke Williamson (Hudson House, The Tripel), who will cook whatever the local harvest yields—a tribute to Montana's rich farming history.

If food isn't the center of your universe (gasp), you can plan your visit around one of the expert-taught Wilderness Workshops, which include Starry Night Photography (Aug. 11–14), Drum Circle Madness (July 2–8), or Champion Horsemanship (Aug. 11–14). But since my life always revolves around my next meal, heightened calorie burn is essential, so at Paws Up I partook in several adventures: the Grizzly Man fitness course, located just down the dirt road from my cabin; a full-throttle ATV ramble on 40 miles' worth of the ranch's seemingly endless trails; an off-trail horseback ride through fields of sage; and a challenging ropes course designed to make you feel doubtful about your footing, even though you're totally secure because you're doubly clipped into a safety line.

With each wobbly plank and swinging beam, metaphors for life abound, becoming stunningly clear at the final obstacle, a mere step into thin air off a 40-foot-high platform. Standing at the precipice, questions come rushing to the fore, not just about the reliability of the mechanized "catch," but also about the depth of your own courage. Since climbing back down the ladder would be the wimpy way out—a painless return to the status quo—you close your eyes and step off into the unknown. And just like that, you're being delicately lowered to the ground like a feather. It worked. You didn't die. In fact, you're more alive than ever.

// Fly direct to Missoula International Airport (MSO) from SFO (via United Airlines) and Oakland (via Allegiant Air), and take advantage of complimentary roundtrip airport transfer. Camping rates start at $530/night per person (depending on the season); The Resort at Paws Up, Greenough, MT, pawsup.com