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 in Jackson Hole.

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

Beneath the shadow of the Tetons, I realized this wasn't just another bucket list check-off… 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 Scenery is Magical

Wyoming is hands down one of the most beautiful places I’ve ever been. And I've been to some gorgeous places (Leichtenstien mountains at sunrise are next level).

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

Jackson is one of those places that, as soon as you arrive, you’re already planning on how you can come 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 staying at the Wyoming Inn of Jackson Hole and absolutely fell in love. As soon as you enter the lobby you’re greeted with a warm, crackling fireplace and fresh cookies that I’m still craving weeks later. The warmth and coziness instantly made me feel at home.

The rooms are just as cozy and inviting. One of my favorite parts of the property has to be the hot tub by the fireplace, that and the sauna at The Lodge at Jackson Hole right next door.

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

They have a free shuttle that will take you practically anywhere you want to go in town. For those of you who want to drive or rent a car, they also have plenty of free parking on the property (which can be pretty hard to come by in Jackson, especially in 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 working there is so contagious that I left the observatory wanting to become an astronomer!

Afterwards, we stayed at the summit to have dinner at the Snow King Mountain Resort’s restaurant, Aurora. You need to try the fondue and the pasta!

4. Downtown is a Western Wonderland

The next morning, we started our day with an amazing breakfast at Wyoming Inn’s restaurant, The Whistling Grizzly, before heading out to explore downtown Jackson.

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

From the candy shops to the cowboy hats, I was tempted to buy just about everything. I already regret not buying a pair of super cute cowboy boots I found, but I will most definitely be buying them as soon as I return.

I love that it’s cowboy everything, and it’s definitely contagious. You’ll want to be a cowboy too by the time you leave.

5. The Caffeine Fixes and Huckleberry Shakes

If you need a recharge from all that shopping, then you definitely need to get a caffeine fix from Cowboy Coffee Company.

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

While you’re downtown, you definitely need to check out Jackson Drug Original Soda Fountain for lunch.

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

I cannot recommend the huckleberry Oreo milkshake enough.

6. Dancing at the Million Dollar Cowboy Bar

If the milkshakes and shopping aren’t enough of a party for you, then what better way to spend the night than to go dancing at the Million Dollar Cowboy Bar.

Saddle up and grab a drink at the bar with the infamous saddle stools, and then join in on the line dancing down 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 need to head back to Wyoming Inn’s Whistling Grizzly. The food here was unreal. Some of my faves 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 really excited to see that on the menu.
• The Main Courses: The Wyoming cowboy pops looked so good that I even considered being a full-on meat-eater for the night. The cavatappi and mushroom dish was simply mouthwatering.
• Dessert: If you know me, then you know that I’m a sucker for dessert, and the Whistling Grizzly did not disappoint. They’re famous for their Whistling Grizzly Carrot Cake, and it was clear why. The carrot cake and the Blood Orange Crème Brulé were incredible.

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

8. Hitting the Slopes

While peak season for Jackson Hole may be in the summer, winter is one of the best times to visit. For those of you who love skiing or snowboarding, you’ll feel right at home.

For those of you (like myself) who have always wanted to try skiing, 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’m convinced that they have the world’s best ski instructor, Paul Dykeman.

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

By the end of the day, I felt like I was ready to head down a black diamond (not really, but my confidence was soaring). I was immediately hooked.

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

9. Winter Wellness and Activities for Non-Skiers

If you’re not a skier or snowboarder, then have no fear, there are tons of other winter activities in Jackson. You can take in the breathtaking Wyoming terrain up close and personal while snowshoeing with the wildlife, or you can try your hand at dog sledding.

If you want something a little less active, then you can always opt for an eco tour where you’ll get to see moose, bison, elk, or other amazing American wildlife.

There is no better way to end a ski trip than a healing trip to Astoria Hot Springs. When your muscles are sore from a day of skiing, then you’ll be extremely glad that you reserved a soak in the natural hot springs surrounded by a surreal Wyoming landscape with both mountain peaks and wide-open space.

For those of you who are brave enough to try it, you can really max out the health benefits by going from the natural hot springs and into the cold plunge. I promise you’ll feel amazing afterwards!

10. It’s Not Just For Winter

While I fell in love with the winter magic, Jackson Hole is an incredible destination all year round.

In the summer and fall, it serves as the perfect gateway to Grand Teton and Yellowstone National Parks.

You can swap the skis for hiking boots, go whitewater rafting down the Snake River, or experience the legendary Jackson Hole Rodeo.

Even the “shoulder seasons” are spectacular for spotting wildlife as the bears and elk are active. No matter when you visit, the vibe is unmatched.

Bonus: The Best Italian Food Outside of Italy

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

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

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

I will absolutely be eating 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 to do it again. I want to bring my family back here to experience it with me.

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

I would love to go back to visit and end up making Jackson my forever home.

_{**Travel Off Path was a guest of Wyoming Inn of Jackson Hole, who helped with the creation of this itinerary by hosting some of our accommodations and attractions. Our opinions, recommendations, and suggestions remain our own.**}