I Spent 48 Hours in Jackson Hole This Fall—Here's Everywhere I'd Go Again

Fall makes a fairly persuasive case for getting out of town. There are leaves to peep, miles to hike, and chilly evenings to spend fireside. And, perhaps most importantly, there’s an excuse to start wearing good clothes again. Suede jackets! Cowboy boots! Big knits! I found a combination of it all on a 72-hour trip to Jackson Hole, Wyoming, packing up an unreasonable number of layers, my husband, and our very tiny dog for the two-plane journey from New York.

It was my first time visiting, though as a fashion editor, I'd heard much ado about Jackson Hole and its many spoils. Five-star resorts, fabulous restaurants, and an increasingly chic crowd have earned it a place alongside Aspen and the Berkshires in the chic-mountain-getaway canon, sans-pretense. The prevailing mood is mellow, easy, and refreshingly unrefined, even when your hotel has a very serious spa and lunch comes with a spectacular view of the Tetons.

And about those Tetons! Step off the plane and there they are—a wall of jagged, Alps-worthy peaks announcing, rather dramatically, that you've arrived. Come fall, the summer crowds have thinned, and the whole valley has reached a cozy off-season sweet spot. It's quiet without being dead, private without feeling deserted, and there's still plenty to do between bouts of admiring the scenery.

After three days of hiking, eating, drinking, and marveling at the Tetons on one sunny lawn or another, I came away convinced that fall might be Jackson Hole's best-kept secret. Here's my guide to making the most of it.

Rent a car. Ubers are expensive, notoriously slow to arrive, and not especially convenient when your itinerary involves bouncing between Jackson, Teton Village, and the national parks. Having your own wheels makes it infinitely easier to explore on your own schedule, and a couple of Ubers will quickly add up to more than a multi-day rental.m

This cozy five-star hotel in the heart of Teton Village makes a compelling case for balancing all that fresh-air virtue with a little indulgence. They hooked up our pooch Pinot with more than one gigantic treat, also offering him his very own food and water bowl and plush bed, which he spent half the trip on while people-watching from our balcony. 

After your longest hike, book a massage in the spa’s intimate treatment room, sweat it out in the cedar dry sauna, then take in the Tetons from the heated outdoor infinity plunge pool. There’s also a 24-hour fitness studio, should you somehow still be itching for exercise.

Sure Hand: A must-visit. Offered the most splendid breakfast a girl could ask for with beautiful bluebird skies and views of paragliders floating overhead.  Do not hesitate to get the corn griddle cakes, which come complete with maple thyme butter and huckleberry lemon compote. We didn’t go for drinks, but rumor has it that the cocktails are fantastic.

Teton Tiger: A welcome departure from traditional mountain-town fare, with Asian-inspired dishes and a lively atmosphere. Service is super warm and cozy; having told our servers our entire life story and taken shots together, we left feeling like family.

The Handle Bar: Come for lunch with a view of the mountains and the upper-crust Four Seasons treatment, stay for the Boot Beer—a ginormous draft poured into a just-as-big boot-shaped glass. An unmissable photo opp.

Silver Dollar Bar: Check the weekly schedule for swing dancing and come prepared to put your cowboy boots to work. Even if you've got two left feet, it's worth going for the Wort Hotel people-watching alone. We went at the recommendation of our server earlier that day and were not disappointed.

Hidden Falls + Inspiration Point: For a relatively easy hike with a spectacular payoff, head to Jenny Lake. Take the boat across to shorten the trek, then continue past the waterfall to Inspiration Point for sweeping views.

Cascade Canyon: For something more ambitious, this longer hike takes you deep into the Tetons, with dramatic mountain scenery and plenty of opportunities for wildlife sightings.

Yellowstone National Park: If you have an extra day to spare, make the drive north to explore one of America’s most extraordinary national parks. Geysers, hot springs, waterfalls, roaming bison—the landscape changes so dramatically from one stretch of road to the next that the drive itself becomes part of the experience. It’s a full-day commitment from Jackson Hole, but one worth making, especially in fall, when thinner crowds make its most famous sights a little easier to take in.

Sunrise Wildlife Safari: Set your alarm obscenely early and head into the park with a guide to spot some of Wyoming's most famous residents.

Mormon Row: You've seen the photographs of the historic T. A. Moulton Barn, framed by the Tetons. Go at sunset to see it for yourself—its a sight to behold.

Rent Bikes: One of the most enjoyable ways to explore Jackson Hole is on two wheels. Rent bikes for an afternoon and take advantage of the area's extensive network of scenic pathways.

Book a Massage at Caldera House: After a day spent hiking, there's nothing quite like surrendering yourself to a massage and an afternoon of spa time.

For Hiking: A puffer vest, leggings, and comfortable sneakers or hiking shoes make an easy daytime uniform. Bring layers, though: Temperatures drop dramatically once the sun goes down.

For Exploring Town: Textured leather jackets, cowboy boots, and all the funky belts and beaded jewelry a girl can wear. For the guys, a bolo tie is always a good idea. Think Western-inspired, without going full costume.

Wondering how to pack like a fashion editor for the mountain town? Discover all of my personal picks ahead.