We literally stumbled upon this beautiful little town on our way to Grand Tetons and Yellowstone and decided to spend a night. Jackson Hole, Wyoming has retained a genuine charm and sense of place that can often get lost as ski towns explode in popularity. If you look out on a clear day you will find yourself wonder-struck by the cascading mountains around you. The old-world charm of Jackson Hole’s wood-plank sidewalks, low-slung Wild West–looking buildings around the main square, and, of course the ever Instagram-able, Antler arch.
Jackson is abuzz with life: trails and outdoor opportunities abound and a great stop on your way to any of the surrounding National Parks however keep in mind that this tinny little town is anything but affordable and make sure to book your stay way in advance. It doesn't really matter where you will stay as the town is quite small and wont make any difference if you decide to book a little bit further from the town square.
In the winter, Jackson Hole is first and foremost a ski town. So hitting the slopes is the name of the game. Make your way to Teton Village and the Jackson Hole Mountain Resort for 4,139 vertical feet of runs.
Off of the slopes, there is so much to see—Grand Tetons National Park and Yellowstone National Park, chief among them. Scenic Safaris offers full-day snowmobile tours of Yellowstone, where the excitement of seeing Old Faithful erupt might take a backseat to navigating past herds of bison or pulling over to track coyotes and bald eagles.
There is plenty of shopping to do in Jackson Hole, including the requisite slightly touristy T-shirt stores and overabundance of art galleries, However, make sure you are well prepared for the mountains weather in advance and don't expect to refurbish your supplies at Jackson as the prices are extremely high and you may end up spending much more then planned.