Your Quintessential 5 Day Jackson Hole Summer Itinerary
Experience summer's highlights
Sunny days, wandering wildlife, and glassy, calm lakes - Jackson in the summertime is simply perfect. Whether you're window shopping through local boutiques, indulging in a delicious meal, or lacing up your boots to hit the trails, JH is the quintessential summer escape.
Day 1
As you land at Jackson Hole Airport, you’ll be greeted by the majestic silhouette of the Teton Range just beyond the runway—one of the most stunning airport views in the world. It’s a short thirteen-minute drive from the airport to The Cloudveil, your base for the adventure ahead. Whether you choose private transportation or a rental arranged by the Pathfinders team, the journey into Jackson sets the tone with wide skies and crisp mountain air.
Upon arrival at The Cloudveil, check in and take some time to relax or freshen up before heading out to explore the Town Square. This iconic center of Jackson is home to the famous elk antler arches, a must for a photo op. If you’re there by 6:00 PM, catch the Jackson Hole Town Square Shootout, where locals bring Old West Days to life with a fun, theatrical reenactment featuring cowboys, outlaws, and saloon girls.
Dinner tonight is at Local, a contemporary steakhouse known for its dry-aged beef, homemade sausages, and a refined wine list. Settle in and enjoy the best of Jackson’s elevated American cuisine.
Day 2
Wake early for a private hiking tour with JH EcoTour Adventures. Their experienced naturalist guides will take you into Yellowstone National Park for an up-close view of Old Faithful and the gorgeous trails surrounding it. You’ll hike scenic paths while learning about the region’s rich ecology, wildlife, and human history—all while soaking in views of the world’s first national park.
After returning to Jackson in the afternoon, unwind at The Cloudveil before heading down to The Bistro, a modern European eatery with an oyster bar, lovely outdoor seating, and a curated selection of wines.
Following dinner, stroll over to the iconic Million Dollar Cowboy Bar. Known for its saddle barstools and neon-lit cowboy sign, it’s the perfect place to listen to live music and experience Western dancing.
Day 3
Start your morning with a short walk to Persephone Bakery, a local gem beloved for its delicious pastries. Over a cup of coffee, you can thoughtfully plan out your day ahead in Grand Teton National Park.
The entrance to GTNP is just a 10 minute drive from Jackson. Once inside the park, enjoy a day of hiking and exploration. Hidden Falls, Inspiration Point, and Cascade Canyon are all excellent trail options for taking in the scenery of alpine lakes and jagged mountain peaks. For a peaceful shortcut across Jenny Lake, take the easily accessible ferry.
Stop at Dornan’s in Moose Junction for lunch on the deck. With panoramic views of the Tetons as your backdrop, it’s one of the most picturesque dining spots in the area.
Back in Jackson, spend the afternoon wandering the local art galleries and boutique shops downtown. Downtown Jackson is the vibrant heart of the town, bustling with life. For dinner, enjoy hand-crafted Italian cuisine at Glorietta Trattoria, known for its fresh pasta and cozy, wood-fired atmosphere.
End the evening at the Jackson Hole Rodeo, a summertime staple running from Memorial Day through Labor Day. It’s a lively and authentic way to experience Wyoming’s deep-rooted cowboy culture. From bareback riding and bull riding to barrel racing and more, the action-packed show offers a true taste of the Wild West.
Day 4
Begin your day with brunch at Café Genevieve, just a short stroll from your room at The Cloudveil. Their eggs benedict is a local favorite, best enjoyed with a Bloody Mary or mimosa.This charming log cabin has plenty of outdoor seating, so you can enjoy your meal with the fresh mountain air.
Following brunch, drive to Teton Village and ascend the summit of Rendezvous Mountain via the aerial tram. The “Top of the World” offers unparalleled panoramic views of the Tetons and Jackson Hole Valley. For the adventurous spirits, high-altitude trails offer the opportunity to hike or mountain bike with incredible views of the valley below.
In the afternoon, embark on a river adventure with the trusted guides of Dave Hansen Whitewater. Choose between a serene, scenic float or an exhilarating whitewater rafting trip down the Snake River. Either way, you’ll experience sweeping canyon landscapes and the chance to spot wildlife—including bald eagles—along the riverbanks.
After some well-earned downtime back at The Cloudveil, head to Snow King Mountain for a remarkable dining experience at Aurora. Ride the gondola to the summit, where the restaurant offers a sophisticated menu, accompanied by stunning mountain views. If you’re lucky, the ethereal Northern Lights may make a rare appearance above the peaks.
Just a few steps away, conclude your evening under the stars at the Snow King Observatory and Planetarium— the perfect finale to your day.
Day 5
Begin your final morning in Jackson with a seamless start, as the team from SUPerior Paddlesports meets you at The Cloudveil. One of their professional staff members will personally deliver and secure your paddleboard rentals to your vehicle, ensuring every detail is attended to with ease. Additional accessories, including premium life jackets and dry bags, are available upon request.
Your destination for the day is String Lake—a serene lake nestled in Grand Teton National Park with gorgeous alpine views. Just 25 miles north of Jackson, the scenic drive takes approximately 45 minutes.
Plan to enjoy lunch on the inviting shores of the lake. Our pathfinders recommend making a stop at Creekside Market and Deli to grab sandwiches and provisions for your relaxed picnic.
Spend your afternoon gliding across String Lake before portaging to Leigh Lake, a hidden gem accessible only by boat or foot. The view of the Grand Tetons reflected in the glassy water is unforgettable. For those seeking further solitude, explore Mystic Isle, a small and idyllic island on Leigh Lake.
After your day out on the lake, head back to the Cloudveil. The team from SUPerior Paddlesports will arrive to receive your rentals, so you can spend time unwinding before dinner.
For your farewell meal, indulge in a thoughtfully curated Japanese meal at Kampai. Led by Executive Chef Chris Massad, of San Francisco’s Akiko’s, Pabu, and Nobu— this meal is nothing short of perfect. Their omakase experience highlights an excellent multi-course tasting menu of sushi and sashimi personally selected by the chef.
End your unforgettable trip by soaking in the hot tub or cozying up near the fire on the rooftop deck as you take in the mountain views, one last opportunity to savor the beauty of your time in Jackson.
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