The Best Way to Spend 5 Days in Jackson Hole, Wyoming

If you’re looking to cross a historic, rugged, and stunning place off your bucket list, you need to pay a visit to Jackson Hole! Whether you love exploring the great outdoors, boutique shopping, or tasting unique flavors, there’s so much to see and do here! We recommend spending at least five days in Jackson Hole, Wyoming. In order to make planning a little easier, we’ve compiled the best ways to spend the week here! For more local recommendations, be sure to access our complimentary Jackson Hole Vacation Guide.

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5 Days in Jackson Hole Wyoming: Your Ultimate Guide

Day One: Settle Into Jaw-Dropping Jackson Hole!

Whether you’re flying in from afar or from just a few hours away, day one in Jackson Hole will call for some rest and relaxation. The first part of Jackson Hole you’ll experience is the Jackson Hole Airport: A small, warmly-lit one that receives direct flights from nine U.S. cities. From the moment you land, you’ll fall in love with this airport’s cabin-esque feel and, of course, the breathtaking Tetons that surround it.

You’ll want to rent a car for your Jackson Hole travels, as there is plenty to see! Once you step into your rental car, you’ll be well on your way to the most relaxing and essential part of your rugged Jackson Hole getaway: Your cozy accommodation at Bentwood Inn! It’s less than 25 minutes from the Jackson Hole Airport. Once our friendly and knowledgeable innkeepers check you in, kick back and relax as you take in the details of your beautifully crafted lodgepole room. Don’t forget your Cottonwood-shaded views of the Tetons! In the evening, head down and enjoy Bentwood Inn’s bistro dining experience: A 4-course dinner prepared by our skilled on-site chef! You’ll love tasting our seasonal, local, and organic offerings.

Day Two: See the Town of Jackson

After a tranquil night of rest in your comfortable bed, wake up to a complimentary gourmet breakfast with us! You’ll be able to do this every morning of your stay, and you won’t want to miss your chance to spot moose in the backyard as you savor a delicious morning meal.

After a fantastic breakfast (and some caffeine to get you going), you’ll be ready to explore! Bentwood Inn is located in serene Wilson, Wyoming, but Jackson—the heart of “the Hole”—is just a 10-minute drive away. Jackson may be a popular stop for out-of-towners, but it retains the look and feel of a village in the Old West. There are countless leather goods shops, Western craft outposts, and historical buildings that appear to have been plucked from the pages of your favorite Western tale. You’ll also discover lots of noteworthy Jackson Hole restaurants and nightlife here, so spend part of day two enjoying it! Don’t forget to snap a photo under downtown Jackson’s famous antler arches before you head back.

Day Three: High Time for a Hiking Adventure

If there’s one activity you must do when in Jackson Hole, it’s hiking! There are so many places to experience gorgeous, rugged backcountry here, but we recommend starting with Grand Teton National Park (located just 10 miles north of Bentwood Inn). Grab your sustaining breakfast at Bentwood Inn, then bring your hiking gear to Grand Teton National Park! This area boasts some of North America’s most stunning landscapes. You’ll be able to see it all from the hundreds of miles of hiking trails that wind throughout the park! Be sure to keep an eye out for majestic wildlife such as moose, bison, elk, and more.

Other incredible hiking spots:

Day Four: Say Yes to Yellowstone!

Did you know that Bentwood Inn is just 63 miles south of Yellowstone National Park? That means you absolutely must wake up early on day four and cross it off your bucket list (that is, if you’re staying in the warmer months when all access roads are open. If you’re staying with us in the winter time, check out some Yellowstone winter tours instead).

Once you go from Jackson Hole to Yellowstone, the possibilities for adventure are endless. If you’re a first-time visitor, we recommend driving a little farther and checking out Old Faithful, the park’s famous geyser. If you have enough time after exploring on your own, check out one of Yellowstone’s wildlife tours. You may even see a wolf—one of the park’s most elusive creatures!

Day Five: Take Advantage of the Season

No matter what time of year you visit, Jackson Hole is a sight to behold. Each season does, however, present restrictions, so be sure to plan ahead. Here is a brief guide to the best activities (and what you’ll want to keep in mind) for each season in Jackson Hole.


Visiting Jackson Hole in the summer? You must go rafting or kayaking on the Snake River! Our summer days are typically sunny, dry, and beautiful—the perfect weather for floating down a gorgeous river surrounded by towering peaks! Summer is our high season, so come prepared to brave crowds. Always make your food, lodging, and activity reservations a few months in advance!


Fall in Jackson Hole is a truly incredible sight. Changing leaves and cooling temperatures make for epic outdoor activity conditions. Whether you prefer hiking, biking, climbing, or wildlife photography, you’ll love fall here. Be sure to check out our Photography Retreat if you’re thinking about a fall getaway to Jackson Hole! Keep in mind that heavy snowfall can take place in autumn here—especially at higher altitudes. If you plan on exploring outdoors, come prepared for rugged, cold conditions and always check the weather in advance.


Winter is a snowy, cold time in Jackson Hole, which makes for excellent skiing conditions! After all, we’re one of North America’s best ski destinations. Though summer is our high season for warm-weather travel, just as many people come in the winter to shred the slopes. Make reservations in advance and be prepared for road closures and snowy weather!


Spring in Jackson Hole can feel a little bit like an extended winter, but that just means more time for winter activities! Skiing conditions are often still excellent through March here, so keep that in mind as you plan your spring getaway to Wyoming. Always check weather forecasts and local news articles to make sure late spring flooding (due to snowmelt) isn’t an issue.

End Each Night Surrounded by the Beauty of the TetonsThe Bunkhouse Room at Bentwood Inn

The first step toward achieving the most amazing five days in Jackson Hole is booking your stay at Bentwood Inn, one of National Geographic’s Unique Lodges of the World! Jackson Hole is a very special place surrounded by natural beauty as far as the eye can see. At Bentwood Inn, we want your boutique lodging experience to reflect that! Here, we uphold a variety of sustainable values. We focus on educating our guests and giving them access to Jackson Hole through responsible vendors. All of our practices (lighting, food preparation, landscaping, etc.) reflect our concern for Jackson Hole’s well-being and sustainability. Learn more about our green initiatives, then pick your perfect home away from home! After five days with us, you may not want to return to the status quo!

Ready to see Jackson Hole for yourself? Check our availability today and start planning your trip! We can’t wait to show you around.