David Agnello

The Million Dollar Cowboy Bar, a drinking landmark.

A buzzy downtown surrounded by national parks makes this the ultimate base for cowboys and millionaires alike

Jen Murphy  – May 14, 2019 | Updated June 11, 2019

Come spring, when the snowcapped peaks of the Tetons start to melt, Jackson Hole sheds its ski-destination image and turns into a family-friendly outdoor playground. Named for fur trapper Davey Jackson, this mountain town hasn’t lost its western spirit. Elk-antler arches grace each corner of the Town Square, and cowboys still rope steer on the rodeo grounds. But this doesn’t mean the town is stuck in the past. Big-city-worthy restaurants, cocktails, shops, and hotels make Jackson one of the most amenity-rich bases for exploring nearby Yellowstone and Grand Tetonnational parks. Photo ops are plentiful in the quieter months of May and June, when wildflowers start to carpet the valley floor and bison calves roam the parks.

8 A.M. Fuel up for a day of adventure at Picnic. Guest roasters supply the coffee, and sister bakery Persephone churns out decadent pastries, like banana Nutella bread, each morning. For a savory hit, try the egg sammy, topped with ricotta, bacon, and pesto.

Jackson Hole Action LLC

Smoked-salmon-and-cucumber toast at Picnic.

9 A.M. Rent a stand-up paddleboard from Rendezvous River Sports ($51, permit included), then drive to Grand Teton National Park and put in at Jackson Lake Dam. If you’ve mastered your balance, navigate the 4.5-mile Class I stretch of the Snake River down to the Pacific Creek Boat Ramp. 

Moritz Wolf / Getty Images

Jackson Lake Dam.

12 P.M. Head back into town and browse the locally owned shops of Gaslight Alley on the corner of North Cache Street and Deloney Ave.
At Made you’ll find handcrafted items such as 45-caliber-bullet cufflinks and letterpress stationery from more than 360 American artisans. For field guides and trail maps, stop by Jackson institution Valley Bookstore.

1 P.M. Lunch on Asian dishes with a mountain twist at The Phoenix and the Dragon, a new walk-in-only spot known for its spicy noodle soups and Korean fried chicken. Save room for a cup of their homemade soft serve.

3 P.M. Spot bison, moose, elk, and more with Jackson Hole Wildlife Safaris ($145/half day). Tours start along the western boundary of the National Elk Refuge and go deep into Grand Teton National Park. Award-winning photographers serve as guides; they can help you frame the perfect shot of the historic homesteads in Antelope Flats, and they know the habits of local wildlife.

7:30 P.M. Both millionaires and cowboys saddle up to the bar at Old Yellowstone Garage in the new Caldera House hotel to dig into gussied-up red-sauce Italian dishes, such as wagyu-meatball-spiked spaghetti.

9 P.M. Back in town, follow the glowing bucking-bronco sign to the Million Dollar Cowboy Bar. Jackson’s infamous watering hole is the spot to go for live honky-tonk performances.

Perfect Night.  The Anvil Hotel (from $195), a 1950s motel turned 49-room inn, has a convenient downtown location. Bonus: the cocktail wizards behind NYC’s Death & Co. crafted the drinks.

Mikael Kennedy

The hip Anvil Hotel.

Getting Here. The airport is only 15 minutes from town, and Jackson Hole Mountain Resort is 15 minutes from there.