Jackson Hole. This place is legit: real wilderness; pristine painterly mountains; air so clean it hurts a little; that freakish Wyoming light that makes even gas stations look like they were art‑directed. Best of all, you can walk out of town and, with a few wrong turns, end up food for something bigger than you. It’s the kind of place where nature is still in charge and no one cares about your follower count.
Some will be quick to point out that this once rugged western town has recently become a rich-guy theme park attracting the hedge‑fund cowboy cosplay crowd in $800 flannels and their well stocked wine cellars, but I say can’t we all get along? The town is still just wild enough—on the fringes and after hours—that if you stay up late, sit in the right bar, and shut up long enough, the real place comes out from under the money.
A Rat Pack weekend in Jackson Hole promises 48 hours of western days and dinner jacket‑adjacent nights: steaks, martinis, live music, and historic bars.
Some thoughts on run of show:
Land in Jackson, check into a downtown base so you can walk everywhere at night:
You may need to call ahead and order them off menu, but a killer way to kick off the weekend is with a round of Rocky Mountain Oysters, or calf fries, you know, “cowboy caviar” – your first shared dare. Order a big shared basket as your first course of the weekend, beers or highballs only—no wine, no spritzes. House rule: everyone eats at least one ball; anyone who taps out buys the first round of martinis that night.
Pro tip: Be sure to talk about the finer points of taste and texture—somewhere between gizzard and clam strip, with that faintly creamy center if they’re not cooked to death—and that slightly metallic, barnyard aftertaste that tells you these nuggets ain’t from Mickey D’s. Eat one, laugh, have another, and you’re in. Flinch, and the West has already decided who you are.
Next walk to Local Restaurant & Bar on Town Square:
Saturday – Western day, Vegas night
For late morning, book a guided, private multi‑gun session run at the Jackson Hole Gun Club, 15–20 minutes south of Town Square and about 30 minutes from Teton Village.
Meet your coach in the parking lot, safety briefing, eye/ear protection. Start on .22 rifles and pistols, then move up to larger‑caliber handguns, AR‑style rifles, cowboy revolvers, and sometimes even .50 cal depending on the package. About 3 hours, fully guided, with up to ~300–400 shots included, drinks/snacks, and all gear.
Alternatives include a scenic Snake River float, a short hike in Grand Teton National Park or horseback riding. In winter, there’s good snowmobiling tours including a robust day out to Yellowstone & Old Faithful – lots of wildlife viewing and winter‑in‑the‑park bragging rights.
Plan on rolling back into town early afternoon for a late lunch and downtime.
Dinner pre-game do a short lounge crawl.
Always remember to drink local: Ask what’s brewed or distilled in Wyoming (Snake River, Roadhouse, Melvin, StillWest, Wyoming Whiskey, Jackson Hole Still Works) and build flights or cocktails around those names.
By now everyone is dog-hungry, leg it to your booked table at Steadfire Modern Chophouse at the Four Seasons:
Cap off the night with a couple of quality sticks and great conversation. Some hotels have outdoor areas for cigars, otherwise Jackson Hole Cigars or Tobacco Row can hook you up with very good humidors and onsite lounges.
Late morning Sunday
Afternoon — Vintage‑style shopping or gallery walk around Town Square; hunt for:
One last quick drink at the Silver Dollar or Cowboy Bar if timing permits—a final martini or highball as you head for the airport.
Jackson Hole is obscenely beautiful year‑round: a valley ringed by the Tetons where the river, the wildlife, and the bars all feel a little too cinematic to be real. Days are for motion—scenic floats on the Snake, hiking and biking under those jagged peaks, wildlife safaris, and summer tram rides out of Teton Village. Nights are for glow—rustic saloons, hunks of meat and cocktail bars humming under a wall of mountains, live music and rugged charm.