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48 hours in Jackson, WY

A three-day guide to the best of Jackson Hole
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Pacaso’s Editorial Team
September 16, 2025
A photo of Jackson, Wyoming, one of the best spots for fall vacations.
Jackson, Wyoming is rugged and wild, brimming with old Western nostalgia and timeless glamour. Nestled in the greater Jackson Hole Valley, this charming mountain town is home to renowned ski resorts, epic mountain views, and a ton of Western flair, all on the doorstep of Grand Teton National Park.
Here, long summer days are made for exploring with endless mountain trails to wander and mouthwatering dining to enjoy. One visit to this ruggedly beautiful town simply isn’t enough. But if you only have a weekend, here’s how to experience the best of Jackson, plus a few hidden gems and local favorites, in just three unforgettable days.

Friday afternoon:

3:00 p.m. | Explore Jackson Town Square

After settling in, stretch your legs with a walk around Jackson Town Square, the heart and soul of the community, framed by massive elk antler arches at each corner. Pop into local shops selling everything from vintage Western trinkets to handmade jewelry and stylish homewares.

4:00 p.m. | Tapas and tannins

Once you’ve worked up an appetite, head to Bin22 for their daily happy hour. Part wine shop, part specialty grocer, part restaurant, it’s a cozy spot with an excellent wine list, European-style tapas, and a patio that locals swear by.

5:30 p.m. | Jackson Hole Shootout

Before dinner, catch the Jackson Hole Shootout, a long-standing tradition that reenacts an Old West gunfight right in Town Square. It’s campy, fun, and a great way to ease into the town’s playful spirit. The show starts at 6 p.m., but crowds begin gathering early for this beloved spectacle.

Friday evening:

7:00 p.m. | Dinner at The Wort

Head to the Silver Dollar Bar inside the historic Wort Hotel—or simply “the Wort,” as locals call it—where you’ll find nightly music and a classic saloon vibe with warm wood interiors and friendly bartenders. Dig into hearty fare like burgers, elk, and their famous corn chowder. Afterward, slip into the Silver Dollar Showroom for live music by local and regional bands.

10:00 p.m. | Nightlife in the Wild West

If you’re still up for more, make your way to the Million Dollar Cowboy Bar, where the barstools are saddles and the bands bring serious boot-stomping energy. It’s rowdy, iconic, and a favorite of locals and visitors alike, and for good reason. 

Saturday morning:

9:00 a.m. | Jackson Hole Farmers Market

Ease into your morning with a relaxed stroll through the Jackson Hole Farmers Market, held on summer Saturdays right in Town Square. Mingle with local vendors and sample fresh pastries, artisan cheeses, and locally made goods.

10:00 a.m. | Coffee and breakfast

After the market, head to Pearl Street Bagels. It’s a beloved local spot with a cult-like following thanks to their fresh bagels, homemade cream cheese, and hot coffee. Bonus: They make their bagels continuously so there are always hot bagels at the ready.

11:30 a.m. | Ride the aerial tram

Head to Teton Village and ride the Jackson Hole Aerial Tram. In just 12 minutes, you’ll ascend over 4,000 vertical feet to the summit of Rendezvous Mountain. It’s one of the most iconic experiences in the area, and requires no hiking boots, no altitude training, and no commitment beyond showing up and taking it all in.At the top, grab a famous gourmet waffle at Corbet’s Cabin and soak in the panoramic views of the Tetons, Jackson Hole valley, and beyond.

Saturday afternoon:

2:00 p.m. | National Museum of Wildlife Art

On your way back into town, consider a quick detour to the National Museum of Wildlife Art, just a few minutes north of the Town Square. Built into the hillside overlooking the National Elk Refuge, this stunning museum showcases American Western and wildlife art, with sculptures lining the cliffside and panoramic views out front.

Saturday evening: 

5:30 p.m. | Early dinner in town

After a day of adventure and exploring, settle in for dinner at The Local Restaurant & Bar, a cozy steakhouse in the town square featuring locally sourced livestock and some of the best burgers in Jackson.

7:00 p.m. | Moo’s Gourmet Ice Cream

Be sure to save room for this fan-favorite ice cream shop. Swing by for a scoop after dinner and don’t forget to try the legendary wild huckleberry flavor.

7:30 p.m. | Jackson Hole Rodeo

If you want the true Jackson experience, there’s no better place to find it than the Jackson Hole Rodeo, a beloved summer tradition running Saturday nights. Expect everything from bull riding to barrel racing, with cheering locals, cowboy hats, and a slice of authentic Western culture.

Sunday morning:

6:30 a.m. | Wildlife Safari in Grand Teton National Park

Wake up bright and early for a one-of-a-kind wildlife safari through Grand Teton National Park. With a local naturalist at the helm, you’ll learn about the region’s wildlife, plantlife, geology, and history—all while scanning for moose, bison, elk, bald eagles, and maybe even a bear. Opt for a private tour for a more intimate and customizable experience, or join a small group for a lively and educational morning in nature.

12:00 p.m. | Brunch

After your safari, make your way to Persephone Bakery, a stylish spot adored by tourists and locals alike. With a shaded patio, delicious coffee, and fresh pastries, you just can’t go wrong.

2:00 p.m. | Last looks and leisure time

Back in town, take one last stroll through Jackson’s shops, including Gaslight Alley, a nook that houses locally owned shops including the popular MADE, which features handmade items from American artists. Take a seat on a patio for a refreshing drink as you bid Jackson a fond farewell for now.See the complete collection of Pacaso homes in Jackson.

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