The Oltre Way
Travel Beyond the Ordinary
Dispatches • Jackson Hole

The Hostel at the Base of the Four Seasons

On $160 ski-in/ski-out, Restaurant Week ramen, Handle Bar après, and the wealthiest zip code that feels the most like you.

Jonathan • The Oltre Way January 2026

Jackson Hole is one of the wealthiest places in the country, and it fits me better than anywhere else I've skied in North America. I don't say this as aspiration or flex. I say it because Teton Village — the compact little base area at the foot of the mountain — has a quality I've been chasing across forty-something countries and have only found in a handful of places: it is upscale, comfortable, cosy, convenient, and not at all performative about any of it. The people here came to ski, not to be seen skiing. The restaurants are genuinely good, not "good for a ski town." The Four Seasons is right there, and so is the hostel, and nobody at either one is confused about what they're doing here.

I landed at 12:11 PM on a nonstop Alaska flight booked for 12,500 American Airlines miles. By 2 PM I had boots on. By 2:15 I was on the tram. A partial day — just the afternoon — but at Jackson Hole a partial day still gives you some of the most dramatic skiing in the lower 48, with the Tetons rising behind you in a way that photographs can't prepare you for. Besides Banff and the Dolomites, I haven't seen a mountain view from a chairlift this stunning anywhere.

• • •

The trip was with my sister. We're building a travel brand together — The Oltre Way — and Jackson Hole was a content trip as much as a ski trip, though we agreed early to capture organically rather than stage anything. This was two weeks after Banff, and we hadn't yet processed the content from that trip. Sometimes the best approach to documenting a place is to just live in it and figure out what mattered later.

We stayed at The Hostel in Teton Village. Private room. Bathroom. Ski-in/ski-out. One hundred and sixty dollars a night. This is the number that makes the rest of the trip make sense, so I'll say it again: $160 a night for a private room at the base of Jackson Hole Mountain Resort, steps from the tram, in a village where the Four Seasons charges north of $800 and Hotel Terra isn't far behind.

The hostel is bare bones. No pool. No sauna. No robes. No minibar. Just a clean room, a bed that does its job, and a location that is — and this is the part that matters — identical to the Four Seasons. Same village. Same tram. Same walk to the same restaurants. The mountain doesn't know where you slept.

$160 a night for ski-in/ski-out at the base of the Tetons. The rest is strategy.

The strategy is this: the hostel saves you $200 or more per night. Over three nights, that's $600 or more that you can redirect to the things that actually define the experience of being in Jackson Hole. And so we did.

The Oltre Way • The Jackson Hole Stack
How to experience Teton Village for half the price

$160/night — The Hostel. Private room, bathroom, ski-in/ski-out.

$50 — Gravity Haus day pass. Pool, hot tub, sauna. The amenities the hostel doesn't have, purchased à la carte for a single afternoon.

$0 — Handle Bar at the Four Seasons. Après-ski drinks and atmosphere. No room key required.

12,500 AA miles — Nonstop Alaska flight. Roughly $350 value, paid in points.

The Gravity Haus day pass was the piece that completed it. Fifty dollars. Pool, hot tub, sauna — the recovery infrastructure that separates a good ski day from a great one, especially when you've been pushing hard terrain. After a full day on the mountain, walking from the hostel to Gravity Haus and sinking into a hot tub with the Tetons in the background felt like something a concierge would arrange at a luxury property. We arranged it ourselves, for the cost of a decent lunch.

• • •

This trip coincided with Teton Village Restaurant Week, which is the kind of timing you can't plan for and shouldn't take for granted. Restaurant Week in a place like Jackson Hole means you're eating at restaurants that normally cater to the private equity crowd, at prix fixe menus that make the food accessible without diminishing it.

Corsa — Italian, and not the kind of Italian that uses "Italian" as an excuse to charge $40 for pasta. Proper Italian, in a mountain town, during Restaurant Week. The kind of meal where you forget you're on a budget and then remember, with pleasant surprise, that you're not spending what you thought.

Shin Shin — ramen. After a cold day on Jackson Hole's terrain, ramen becomes less a meal and more a medical intervention. Hot broth, noodles, the slow thaw of hands and face and core temperature. Shin Shin understands that après-ski food doesn't need to be fancy. It needs to be warm, it needs to be immediate, and it needs to meet you exactly where you are, which is exhausted and happy and salt-depleted.

And then the Handle Bar at the Four Seasons. This is the move. The Handle Bar has the Four Seasons polish — the service, the ambiance, the wine list, the fire — without the Four Seasons room rate attached to it. You walk in from the cold, order something good, sit by the fire, and watch the Tetons through floor-to-ceiling windows while the afternoon light turns the snow pink. Nobody asks where you're staying. Nobody needs to know. The experience is the same whether you walked from the penthouse or from the hostel down the road. You're buying the après, not the address.

On belonging in expensive places

People ask what kind of person goes to Jackson Hole. The answer has always been a specific type: affluent, performance-oriented, the Arc'teryx-everything crowd who talk about Corbet's Couloir and humble-brag about skiing the tram in whiteout conditions. Private equity at the Four Seasons. Old money that thinks Vail is too corporate and Aspen too scene-y. It's performing rugged authenticity while embedded in luxury consumption — Wyoming, cowboys, "real" mountain culture, with $600-a-night hotels and $40 craft cocktails.

Teton Village subverts this, or at least the version of it I experienced does. The village is too compact for pretension. Everything is a five-minute walk: tram, restaurants, après, done. No driving between town and mountain. No navigating a sprawling resort complex. It has a European base-village quality — intimate, functional, complete. People are here because they want to ski hard terrain and eat well afterward, not because they want to be photographed in their Moncler.

I said to my sister, somewhere between the Handle Bar and the hostel, that it was fitting that the place that feels most like me is one of the wealthiest zip codes in the country. She laughed. But the observation is real: my taste runs toward places and experiences that wealthy people have identified as genuinely good — not just expensive, but good. The difference is I'm accessing it through strategy rather than capital. The hostel and the Handle Bar. The Gravity Haus day pass and the Restaurant Week prix fixe. The 12,500 miles and the afternoon partial day.

Someday the income catches up to the taste. For now, the strategy is the point. And the strategy — at least in Teton Village — works beautifully.

Monday was a full day. Tuesday was partial — we needed to be off the mountain by early afternoon to make a 5:30 PM flight, and Jackson Hole Airport's proximity to the resort (the only commercial airport inside a national park) meant we could squeeze every possible minute out of the morning. Two and a half days of skiing. Zero PTO used — I had my phone for Teams messages, took my morning meetings from the hostel, and was on the mountain by late morning. The same remote-work flexibility that lets me ski Utah every other week made Jackson Hole possible on a regular workweek.

The flight home was tight. The week ahead was already filling in: SLC in two weeks for Sundance and more skiing, staying at my sister's house in Sugarhouse with her spare car and standby flights. Then maybe a European ski trip — Megève, Ischgl, Chamonix — then Italy with the family in the fall, then Uzbekistan, then the Colombian rainforest retreat. The year was assembling itself the way it always does: winter for mountains, spring for culture, fall for transformation.

I don't want to make it work with hostels forever. The strategy is elegant now, but there's a version of this where the income matches the taste and I just book the room because I can. That's what I'm building toward.

But for now — and I mean this without resignation, with something closer to satisfaction — the hostel at the base of the Four Seasons is not a compromise. It's a proof of concept. That the experience of a place is not locked behind the room rate. That the Tetons look exactly the same from the Handle Bar whether you slept on a $160 mattress or an $800 one. That Corsa during Restaurant Week and Shin Shin ramen after a powder day and the Gravity Haus hot tub with the mountains in the background are available to anyone who knows where to look and what to prioritize.

Jackson Hole is the kind of place that was made for people with more money than I have. I went anyway. And I didn't miss a thing.

Previous Dispatch Banff: Record Snow & the Post Hotel Series Winter Dispatches — Jan 2026