Field Report No. 20 · Couples trip
Jackson Hole Wyoming, USA
Two Octobers in a row, just the two of us: whiskey on the saddle stools at the Cowboy Bar, horses at Diamond Cross Ranch, and mountains that come out of the ground vertical.
Field Report
No. 20
Couples trip
Jackson Hole Wyoming, USA
Worth the flight.
- Coordinates
- 43.4799° N, 110.7624° W
- Traveled
- October, 2024 & 2025
- Kid-readiness
- We haven't brought the girls yet. Both trips were just the two of us, so there's no kid section to fake.
- Where we stayed
- The Cloudveil, right on Town Square, twice. Great location, great vibe. You walk to dinner, the bar, and the antler arches from the front door.
- The non-negotiable
- A shot of whiskey at the Million Dollar Cowboy Bar, sitting at the bar on the saddle stools. We do it every trip.
- What we'd skip
- Trying to hike straight up anything near the ski resort your first morning. These mountains come out of the ground vertical, and they will humble you before lunch.
- Best season
- October, both times, and the weather was amazing both times. The valley grass goes gold and the crowds thin out.
- Points & hacking
- Jackson Hole (JAC) is the rare airport inside a national park, so award seats can be tight and pricey. Flying into a bigger hub and driving in is the cheaper points play.
43.4799° N, 110.7624° W
Jackson Hole is really freaking cool, and it’s nothing like Colorado. The valley floor is these amber grass fields, and then the Tetons just pop straight up out of them with no foothills, no warning, sharp as anything we’ve seen in the Lower 48. Jamey learned that the hard way on the first trip: tried to hike a mountain by the ski lift the next morning and it destroyed him. It’s that vertical. We’ve now gone two Octobers in a row, both times without the girls, and both times the weather was perfect.
We stay at The Cloudveil, right on Town Square, and we’d book it a third time without looking anywhere else. Great location, great vibe, and everything below is a short walk from the front door.
You have to get a drink at the Million Dollar Cowboy Bar. Sit at the bar on the saddle stools and order a shot of whiskey. We do it every single trip.
The Million Dollar Cowboy Bar has been on the square since 1937, the bar stools are genuine saddles, and there are 624 silver dollars inlaid into the bar top. It’s touristy in the way that’s actually earned. From there the eating in this town runs deep: Gun Barrel Steak & Game House is dinner surrounded by the taxidermy of the old Wyoming Wildlife Museum (the menu runs to bison ribs and elk chops), Snake River Grill on the square is the fine-dining night (reservations open three months out and you need one; closed Sundays), and Café Genevieve, the little blue 1906 log cabin a block off the square, does breakfast worth planning around. Ask about the Pig Candy. Melissa’s spot is Persephone Bakery: French pastries and good coffee on a little patio. It fills up, so go early.
The one experience we’d tell you to book
Diamond Cross Ranch. We’ve done it twice and it’s unreal: a working ranch at the base of the Tetons, horses against that skyline, private rides that don’t lump you in with strangers, and we’ve eaten out there too. It runs May through late October, which is one more argument for the fall trip.
For the park day, we’ve done Jenny Lake and the hike out to Hidden Falls and Inspiration Point, which is the right size at three to four miles with the boat shuttle across the lake. Back in town, the girls in our crew always end up at Kemo Sabe getting custom hats fitted, and yes, you take the picture under the antler arch on Town Square. The whole town is a vibe, and we mean that as the highest compliment we give.
