10 reasons why Jackson Hole should be your number one getaway in 2026

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I’ve traveled the world, but nothing prepared me for the moment I stepped off the plane Jackson hole.

The jagged silhouette of the mountains against the skyline immediately grabs your attention, promising an adventure that feels both wild and welcoming.

Under the shadow of the Tetons, I realized this wasn’t just checking off my bucket list… it was a place I never wanted to leave.

Here are 10 reasons why I think Jackson Hole should be on your 2026 bucket list:

1. The landscape is magical

Wyoming is without a doubt one of the most beautiful places I have ever been. And I’ve been to some beautiful places (The Leichtenstien mountains at sunrise are next level).

I can’t even begin to describe how magical Wyoming is in the winter. From the snow-capped peaks of the Tetons to the wide open spaces filled with wildlife, I was hooked.

Jackson is one of those places where as soon as you arrive you are already planning how to get back and never leave.

In fact, that was the story of most of the people we met who live in Jackson; they came to visit and decided to stay forever.

2. The warmest welcome at Wyoming Inn

I recently had the pleasure of being in the Wyoming Inn of Jackson Hole and absolutely fell in love. As soon as you enter the lobby you are greeted with a warm, crackling fireplace fresh cookies which I still long for weeks later. The warmth and coziness made me feel immediately at home.

The rooms are just so cozy and inviting. One of my favorite parts of the building has to be the hot tub by the fireplacethat and the sauna The Lodge at Jackson Hole right next door.

As a bonus, so is Wyoming Inn and its sister property, The Lodge at Jackson Hole less than five minutes from the heart of downtown Jackson.

They have a free shuttle that will take you pretty much anywhere you want to go in the city. For those of you who want to drive or rent a car, that is also possible ample free parking on site (which can be quite difficult to find in Jackson, especially in the winter when you can’t park on the street).

And the off-season prices are extremely reasonable!

3. Starry nights on Snow King Mountain

On our first night we went to the top of Snow King Mountain to the Snow King Observatory and Planetarium where we spent the evening learning about the stars.

The passion of the people who work there is so infectious that I left the observatory wanting to become an astronomer!

Then we stayed at the summit to have dinner at the Snow King Mountain Resort restaurant, Aurora. You must try the fondue and the pasta!

4. Downtown is a western wonderland

The next morning we started our day with a great breakfast at the Wyoming Inn restaurant, The whistling grizzlybefore heading out to explore downtown Jackson.

The shops in Jackson are so cute! When they’re covered in snow, they almost look like they could be Santa’s village with a western touch.

From the candy stores to the cowboy hats, I was tempted to buy just about everything. I’m already regretting not buying a pair of super cute cowboy boots I found, but I will definitely buy them as soon as I get back.

I love that it is cowboy everything, and it is certainly contagious. By the time you leave, you’ll want to be a cowboy too.

5. The caffeine fixes and huckleberry shakes

If you need a break from all that shopping, you’ll definitely need a caffeine fix Cowboy Coffee Company.

They were so nice and went out of their way to give me one sugar cookie iced chai latte even though it wasn’t technically on the menu, and it was AMAZING.

While you’re downtown, be sure to check it out Jackson Drug Original Soda Fountain for lunch.

Their salads and burgers are great, but the real magic is in their milkshakes.

I can do the blueberry Oreo milkshake enough.

6. Dancing at the Million Dollar Cowboy Bar

If the milkshakes and shopping aren’t enough of a party for you, what better way to spend the night than going dancing in the Million dollar cowboy bar.

Get in the saddle and grab a drink at the bar with the infamous saddle stools, and then join in the line dancing on the dance floor.

You’ll be partying like a cowboy in no time.

7. A foodie’s dream at The Whistling Grizzly

For dinner you absolutely have to go back to Wyoming Inn’s Whistling Grizzly. The food here was unreal. Some of my favorites were:

• The Jumbo Garlic Shrimp: It was so good and Actually jumbo (it was literally the size of my hand)! I’m a pescatarian so I was very excited to see that on the menu.
• The main courses: The Wyoming cowboy pops looked so good that I even considered being a full-fledged meat eater for the evening. The cavatappi and mushroom dish was simply delicious.
• Dessert: If you know me, you know I love desserts, and the Whistling Grizzly did not disappoint. They are known for their Whistling Grizzly Carrot Cake, and it was clear why. The carrot cake and the Blood Orange Crème Brulé were incredible.

I may come back to stay at the Wyoming Inn just to eat here again.

8. Hit the slopes

Although peak season for Jackson Hole may be in the summer, Winter is one of the best times to visit. For those of you who enjoy skiing or snowboarding, you will feel right at home.

For those of you (like myself) who have always wanted to ski, then this is the perfect place for you. Jackson Hole mountain resort is great for any ski/snowboarder level. I had never tried skiing before, and I am convinced they have the best ski instructor in the world, Paul Dykeman.

He was patient, friendly and gave clear and concise instructions. Paul made me feel comfortable and safe the entire time. I’m sure there were times when I looked absolutely ridiculous, but he never made me feel like I looked weird.

By the end of the day I felt like I was ready to go to a black diamond (not really, but my self-confidence soared). I was immediately hooked.

All I’ve talked about is going back to Jackson Hole Mountain Resort to ski again (my husband can confirm this). Everyone at the resort was great to work with, and I wanted to be friends with all of them.

9. Winter wellness and activities for non-skiers

If you’re not a skier or snowboarder, have no fear: there are plenty of other winter activities in Jackson. You can get up close and personal with Wyoming’s breathtaking terrain on a snowshoe hike with the wildlife, or you can try dog sledding.

If you want something less active, that is always possible choose an eco tour where you can see elk, bison, moose and other amazing American wildlife.

There’s no better way to end a ski trip than with one healing journey to Astoria Hot Springs. If your muscles are sore after a day of skiing, you’ll be extremely glad you booked a soak in the natural hot springs, surrounded by a surreal Wyoming landscape of both mountain peaks and wide open space.

For those of you brave enough to try it, you can really maximize the health benefits by going from the natural hot springs to the cold dip. I promise you will feel great afterwards!

10. It’s not just for winter

Although I fell in love with the winter magic, Jackson Hole is an incredible destination any time of year.

In summer and fall it serves as the perfect gateway Grand Teton And Yellowstone National parks.

You can trade your skis for hiking boots, go rafting on the Snake River or experience the legendary Jackson Hole Rodeo.

Even the “shoulder seasons” are spectacular for wildlife viewing, as bears and elk are active. No matter when you visit, the atmosphere is second to none.

Bonus: the best Italian food outside of Italy

Before you leave Jackson, you need to eat Orsetto Italian bar and eatery. This was by far the best Italian food I’ve had outside of Italy.

Everything we ate was incredible. Although everything we ate was delicious, I still had a few favorites.

• The Bruschetta: First of all, you have to try this. I can’t emphasize that enough.
• The Cacio e Pepe: You should also try this pasta. I promise you’ll thank me later.

I will absolutely eat at Orsetto again.

I can’t wait to come back!

Everything I did in Jackson made me feel like I couldn’t wait to come back and do it again. I want to bring my family here to experience it with me.

Honestly, I’d like to be one of the stories we kept hearing from the locals.

I would love to go back and visit Jackson and eventually make it my forever home.

Liz Fox

Liz is the Press and Marketing Manager at Travel Off Path and the genius behind The Upgrade newsletter, where she connects our readers with the best travel tips, secrets and advice twice a week. An avid adventurer herself, Liz enjoys horse riding, exploring historic sites and walking through beautiful landscapes, and embodies the adventurous spirit that Travel Off Path stands for.