This past summer, my wife and I took a 1,300-mile road trip with our 1-year-old, leaving Spokane, Washington, and heading to Bozeman, Montana, and looping through two of our most beautiful national parks: Yellowstone and Grand Teton. There were many incredible stops along the way including Jackson, Wyoming, a place we would both hope to visit again.

Her Perspective

Jackson, Wyoming, is an easy place to love.  The town, together with the surrounding area, is known as Jackson Hole—and the two names are frequently used interchangeably, albeit incorrectly—but however it is referred to, it is nothing short of breathtaking. Flat ranch land ends abruptly into the base of steep mountain slopes, creating a rich ecosystem inhabited by the likes of moose, wolves and bears. In town you’ll find Western-style storefronts and historic wooden boardwalks connecting many shops and restaurants, which are a charming reminder of Jackson’s cowboy roots. It won’t surprise you that a John Wayne movie was filmed here.

Jackson caters to all tastes and styles, with offerings ranging from the luxurious to the rustic. Multiple area resorts offer spa and wellness treatments and high-end accommodations. Boutique shops and art galleries dot the streets, between coffee shops and restaurants advertising buffalo burgers. A nightly “Shootout” is performed during summer months by the Jackson Hole Playhouse, which also hosts a popular Western-style comedy and dinner stage show. 

Snake River Brewing sits a short walk from the town square and is absolutely worth a visit. The micro-brewery boasts an excellent slate of beers and a delicious, ever-rotating food menu to match.

Just beyond the city limits, a recreational paradise awaits, with endless options for exploring the valley and mountains. Whitewater rafting and horseback riding are available to those seeking an organized outing. Those looking to build their own adventure will find hundreds of miles of biking and hiking trails to navigate.

As you might imagine for a place surrounded by massive peaks, Jackson is magical in the winter. The town serves as a cozy oasis in the valley nestled between three ski resorts. Snow King Resort quite literally runs into the edge of town. It is so close you’ll feel like you are already at the lodge while standing in the town square. If hitting the slopes is not your style, other popular winter activities include snowmobiling, Nordic skiing and dogsled trips. Plus, there is always the shopping and spas.

Jackson serves as an excellent jumping-off point for visiting the area’s two national parks: Grand Teton and Yellowstone. Nearby Grand Teton Nation Park is a must-visit. Regardless of the season, the star of the park is the stunning 40-mile long Teton Range, with its highest peak, for which the park is named, checking in at nearly 14,000 feet. A lake hugs the base of the peaks and is great for kayaking, paddle boarding and skipping rocks. With snow-capped peaks year-around, you’ll take more photos of the scene than you care to admit—or your spouse will believe is necessary—but the landscape is so striking you’ll feel compelled to do so (so it’s really not your fault).  Watching the sun slowly sink behind the peaks is a perfect way to end a day exploring the park and the surrounding valley area.

Jackson is not an unknown gem. On a summer day, at the height of the tourist season for the nearby national parks, it is not uncommon to see a long lineup of cars from the north slowly inching into Jackson with passengers eager for a break from the outdoors, lunch and a tank of gas. The wait is well worth it, as this lovely little town has much to offer. You’ll quickly learn that you may come to Jackson Hole for the scenery—but you’ll stay for the cowboy charm.

His Perspective

One of my first thoughts upon driving south into Jackson was, “Man, we need to come back here in the winter.” While the town’s official name is Jackson, it’s easy to see where the Jackson Hole name comes from, as being in the center of town surrounded by stunning peaks you do feel like you’ve fallen down a rabbit hole. The surrounding peaks are home to three ski hills: Jackson Hole Mountain Resort, Snow King and Grand Targhee. Teton Village is also not far to the northwest, and although I’ve yet to ride any of these mountains, a quick study of the trail guides suggests that a winter week in Jackson would be burning calves and cramped thighs, but plenty of fun memories.

But back to summer and the trip at hand. After a few nights camping and lots of sightseeing in the car, it was time to find a meal and stroll the streets of the city. As we were traveling in the busy summer months, stop-and-go traffic started forming about 2 miles outside of town. With all the recreation and national parks in the surrounding area, the town swells during summer. We were able to locate a parking spot, and thankfully Jackson is very easy to walk around, even with a baby in tow. I’ve been to many ‘themed’ towns in my travels, and the presentation of this traditional Western community was apparent from the first few steps. Facades on the storefronts all beckon you back to the late 1800s, and wooden-raised sidewalks added to the charm. Some might find it a little cheesy to walk by high-end stores, art galleries and fly shops all done up to look old and rustic, but I suppose that depends on how you see the world.

It’s no secret that there is no lack of wealth in this community. One really cool feature is the four arches made of elk antlers at the town square. Local boy scouts collect the antlers from the nearby National Elk Refuge, and every couple of decades the old antlers are replaced with new ones—some 10,000 pounds worth!

While the population is less than 12,000 permanent residents, seasonal workers and wealthy business owners and celebrities create a much larger demographic. While we didn’t see any famous stars of screen or stage, not that we were looking too hard, it’s not an uncommon sight any time of year. One look at the listings in the multiple real estate offices will show you what kind of income you’ll need to afford even a modest place around here. There are plenty of high-end restaurants, but I was pleased to see plenty of more laid-back, local and affordable places as well, like where we had lunch—Snake River Brewing, the oldest brewery in Wyoming.

On the way out of town there were dozens of fly fishermen casting a line and many bicyclists taking advantage of the paved trail that leads all the way into Grand Teton National Park. While the peaks are massive, the valley below is very flat, making this an excellent place to go bike camping, as the trails are easy, paved and well maintained.

With such incredible beauty and immense outdoor activities, it’s not surprising people pay small fortunes to live here. Still, the town maintains a pleasant Western charm and offers enough to see and do without you having to be Oprah rich to enjoy it.

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