There Is Something To Be Said About Authenticity: Jackson Hole

Jackson, I think you might be my favorite ski-town.


I’m not afraid to say it. Even though I traveled here during the early ski season, I couldn’t have experienced better conditions. Unfortunately, I was only able to come for a long weekend and snowboarded twice. But what I took away from this destination lingered with me for weeks to follow.

We’ve traveled to a lot of places and some really cool mountain towns but there was something a little different about Jackson.

I can’t quite put my finger on it but maybe because it felt truly authentic. One of the problems with a lot of ski towns or villages is that they feel inundated with luxury shopping, restaurants, and the clientele needed to keep those places in business. Sure, Jackson had some really expensive restaurants and hotels but they were able to preserve the western mountain town “feel”.

During my flight from Denver to Jackson, I noticed something a little strange. The plane was a small jet to take us the 1.5 hours into Wyoming and everyone was chatting with each other. Not totally uncommon while boarding and flying but it just didn’t stop. I had to take off my headphones and eavesdrop a bit.

What I was beginning to realize was that everyone on this flight actually knew each other. They were all part of the “Jackson club”.

That’s not a real club, to my knowledge, but they chatted about why they had to leave Jackson, what their plans were when they got back, etc. It didn’t feel like a typical flight. Jackson does have a bit of a reputation for being exclusive. The mansions are easy to spot while you’re driving around but the more time I spent there the more I realized it is like a small, unspoken club.

Some ski resorts and the surrounding towns can have a Disney feel to them. Lodges are made to mimic those in the Swiss Alps, chain restaurants sitting next to a Gucci store, and basically no sign of a local anywhere to be found.

Jackson did not feel manufactured. The lodge at the base of the mountain was not even impressive and the base area was one of the most basic I’ve seen. That’s not an insult at all. That’s actually amazing because it keeps the emphasis on the mountain and the riding.

The town of Jackson, only 15-20 minute drive away, had the same vibe. Cowboy bars, friendly locals, and cheap accommodations. Some restaurants definitely tried to be fancy but left the pretentiousness out of the equation. Everyone here was down to earth and more worried about what type of activity they would be participating in that weekend. With Grand Teton National Park surrounding the town, you can have your pick. Ski in the morning, snowmobile in the afternoon, ride some horses in the evening? Doesn’t matter. Get outside and do something.

I’ve been snowboarding for at least 15 years, maybe more, and I’ve never actually spent a day by myself on a mountain. Sure, I’ve been separated from friends for a long time but heading there solo was a totally different animal. My first day it was just me, the mountain, and a blue-bird sky. Stashes of fresh powder were to be had if you meandered a little and I’m sure to a Jackson local this would be considered a mediocre day. Not for us east-coasters! I was a pig in shit!


There was something nice about experiencing this place for the first time, solo. Clear, unobstructed views of the valley and the Tetons were stunning. The mountain makes you feel as if you are in the backcountry and not stuck dodging others down a narrow trail. Everything about it was amazing.

The second day of riding I was accompanied by some friends and 8 inches of fresh pow! Another epic day of riding but something was different about the first day. I felt a real connection to Jackson as soon as I stood on top of the slopes and wondered what I had to do to become part of the “club."

Whenever we depart a new place, Cydny and I always asked each other, “could we live here?” We could live a lot of places if we wanted but there are only a handful that really stick out. As of right now, Jackson might sit at the very top.

Just go and see for yourself! 

FAVORITE EATS: Gather (american): The korean short ribs and brussel sprouts appetizers were incredible!

FAVORITE BAR: Local Restaurant & Bar: Full disclosure, I didn’t have a sip of alcohol while in Jackson but this place had great bartenders and whiskey selection looked robust.

FAVORITE MEAL: Eggs Blackstone from Jackson Hole Coffee Roasters. Quaint breakfast spot. The Eggs Blackstone blew me away, basically their eggs benedict. Great little spot!