Tucked between majestic mountain ranges and wildflower-filled valleys, Jackson Hole, Wyoming, is the kind of place that feels like it was made for travelers who love adventure with a side of elevated comfort. From panoramic hikes in Grand Teton National Park to rooftop cocktails and local fare, this curated Jackson Hole itinerary blends nature, indulgence, and charm-all in a weekend.

Whether you're planning a romantic getaway or a friends’ escape, here’s how to spend a perfect Spring or Summer weekend in Jackson Hole.

Where to Stay in Jackson Hole

For a central stay that combines rustic elegance with unbeatable access to town and trails, The Cloudveil is a standout. Located right on Town Square, this Autograph Collection property offers luxe accommodations, complimentary gear rentals, and an unbeatable rooftop for golden hour cocktails.

Prefer an ultra-private retreat? Amangani, perched high above the valley, offers sweeping views and a world-class spa experience.

Allure Travel Co. Tip: At Allure Travel Co., we have partnerships with thousands of hotels around the world. Booking a stay through us is a complimentary service—meaning no extra cost to you! Not only will you save valuable time, but you’ll also unlock exclusive perks (like hotel credits and complimentary room upgrades, if available) and experience VIP treatment throughout your stay.

Day 1:

Morning: Grand Teton National Park Adventure

Begin the day with an early drive to Grand Teton National Park-just 15 minutes from downtown. Entry is $35 per vehicle and valid for seven days. Two must-do hikes are:

Taggart Lake Trail (3.8 miles round trip): Easier, scenic, and postcard-worthy.
Hidden Falls Trail (5-6 miles depending on your start point): A little more effort, but absolutely worth the payoff.

Pro tip: Be sure to bring bug spray, sunscreen, and plenty of water. For more tips, check out our full guide of the Grand Tetons.

Afternoon: Rest & Rooftop

After soaking in the beauty of Grand Teton National Park, head back to The Cloudveil to refresh. Their rooftop lounge is perfect for unwinding with a cocktail and light bites while watching the sun dip behind the Tetons.

Dinner: The Bistro

Located inside The Cloudveil, The Bistro offers French-inspired mountain cuisine in an upscale yet approachable setting. Signature dishes include: Chickpea Fries, Smoked Trout Croquettes, Ricotta Pillows (a fan favorite!) , and Steak Frites Au Poivre.

Evening Sweet Treat: Moo’s Gourmet Ice Cream

No trip to Jackson Hole is complete without a scoop of Wild Huckleberry Ice Cream from Moo’s, just across the street. It’s been voted the #1 dessert in Wyoming for good reason.

Optional Nightcap: Silver Dollar Bar

Wrap the night with live music and a Western-chic atmosphere at the Silver Dollar Bar-a local staple featuring over 2,000 inlaid silver dollars in the bar itself.

Day 2:

Breakfast: Persephone Bakery

Start with coffee and a gourmet egg sandwich from Persephone Bakery. This charming café is a local favorite, offering pastries, fresh breakfast options, and a quaint courtyard.

Morning Activity: Jackson Hole Farmers Market

Held every Saturday in Town Square (8am–12pm), the Jackson Hole Farmers Market has regional produce, artisan goods, and local flavors. It’s the perfect place to pick up a souvenir or snack.

Late Morning: Scenic Drive Through the Tetons

Instead of hiking, take a leisurely drive through Grand Teton National Park, stopping at overlooks like: Snake River Overlook, Oxbow Bend, and Jenny Lake Overlook. Bring a picnic or plan for lunch with a view!

Lunch or Afternoon Drink: Snake River Brewing

If you're craving craft brews and casual bites, Snake River Brewing is a great stop. It's a relaxed spot that pairs well with a scenic afternoon.

Dinner: Snake River Grill

For your final dinner, Snake River Grill is a must. Known for its elevated mountain cuisine and moody lodge-style ambiance, this restaurant serves iconic dishes like: SRG Potato Pancake, Steak Tartare Pizza, Risotto & Roasted Carrots, and their Classic Filet or Pork Chop.

Reservations highly recommended, or opt for bar seating if you’re in a pinch!

Evening: Million Dollar Cowboy Bar or the Jackson Hole Rodeo

Million Dollar Cowboy Bar is a Western icon with saddle bar stools, pool tables, and live country tunes.

Jackson Hole Rodeo (summer only): An authentic, family-friendly experience showcasing rodeo events like barrel racing and bull riding. Grab tickets in advance and arrive early for the best seats.

Day 3 (Optional):

Breakfast: Café Genevieve

Set in a historic log cabin, Café Genevieve serves Southern-inspired comfort food. The Cajun gravy biscuits are a must, and it’s a cozy send-off before departure.

Explore Town Square

Spend your last morning browsing boutiques and galleries in Jackson’s Town Center. The antler arch entrances, local shops, and walkable vibe make this a charming finale to your weekend.

In Conclusion…

From trailheads to tastings, Jackson Hole is the perfect destination for a luxury weekend immersed in nature and local charm.

Interested in booking a trip to Jackson Hole?

At Allure Travel Co., we don’t just plan trips—we curate experiences. We offer bespoke travel planning, luxury hotel bookings, and travel concierge services. If you’re looking for full-service planning or to simply elevate your experience, we’d love to work with you!

Weekend in Jackson Hole: A Luxury 2-Day Itinerary for Adventure and Relaxation