📍 Jackson Hole, Wyoming | 🗓️ May 26–31, 2025
There’s something incredibly special about traveling with multiple generations of family. This May, our crew of grandparents, parents, and kids all gathered in Jackson Hole for six unforgettable days of nature, adventure, and connection. Here’s how we made the most of every moment!
🛬 Day 1: Welcome to the Wild West
📅 May 26 | 🕓 4 PM Check-In
We arrived a bit later than planned, but here’s what our ideal first evening would have looked like: After settling in, we would have taken a leisurely stroll through downtown Jackson to get our bearings. With its wooden boardwalks and the iconic elk antler arches in the town square, the area feels like a scene straight out of a classic Western. (Although this wasn’t my first time in Jackson, this quickly became our favorite way to end the day.)
🍕 Dinner: Hand Fire Pizza
A local favorite in a renovated old theater. We shared pizza and toasted the start of our big family adventure.
📸 Instagram-worthy moment: The lit-up Hand Fire Pizza sign makes the perfect first-night photo op.
💦🐎 Day 2: Soaks, Saddles & Steak
📅 May 27
- Morning: Breakfast, then off to Granite & Astoria Hot Springs. A relaxing soak with views of the Snake River = pure bliss.
- Afternoon: Horseback Riding —Even Grandpa saddled up and loved it!
- Evening: Dinner at Local Restaurant & Bar (5:30 PM reservation). Excellent Wyoming beef and a cozy vibe right on the square.
📸 Pro tip: Snap a family photo on horseback—you’ll cherish it forever.
🌋 Day 3: Yellowstone Wonders
📅 May 28
This was our day trip to Yellowstone National Park, and it was absolutely worth the early start.
Highlights included:
- Old Faithful erupting right on cue.
- Walking the boardwalks over steaming geothermal pools.
- Spotting bison herds across the plains.
🍔 Dinner: Jackson Drug
A throwback soda fountain and burger stop—perfect for post-park comfort food. And dessert!
📸 Must-capture: The rainbow-colored Grand Prismatic Spring is unreal in photos. Do the Grand Prismatic Springs Overlook trail for the view.
🌊 Day 4: Rapids & Relaxation
📅 May 29
- Morning: Whitewater Rafting (9 AM–12 PM) 🌊
An unforgettable ride down the Snake River—just the right mix of thrill and scenery for all ages. - Lunch: Hatch – fresh tacos, bold flavors, and a laid-back vibe 🌮
- Afternoon: Free time to rest, explore shops in town, or simply soak in the mountain air
- Dinner: Orsetto (7:00 PM reservations) – cozy Italian-American comfort food with something for everyone 🍝
It was a more relaxed evening, and after the morning’s adventure on the water, the downtime was exactly what we needed.
🌄🥾 Day 5: Trails, Lakes & a Mountain-Top Feast
📅 May 30
- Sunrise: Schwabacher’s Landing – peaceful, stunning, and worth the early wake-up (so I hear…)
- Hiking: Tackled the Taggart Lake Trail and visited String & Leigh Lakes.
- Lunch: Planned to picnic, ended up at Dornan’s Pizza & Pasta instead 🍕
- Dinner: Aurora at Jackson Hole Gondola (7 PM reservation). A mountain-top meal with a gondola ride and panoramic views of the Tetons.
📸 Golden Hour Alert: Schwabacher’s Landing is the photo spot for Teton reflections.
👋 Day 6: One Last Look
📅 May 31 | 🕙 10 AM Checkout
We had a slow morning packing up, sharing photos, and promising to return. Jackson Hole gave us so many shared memories—from thrilling adventures to quiet nature moments.
💡 Why Jackson Hole Works for All Ages
- Adventure for the young and young-at-heart: rafting, riding, hiking.
- Relaxation for the whole crew: hot springs, scenic drives, peaceful lakes.
- Tons of variety: cowboy culture, national parks, fine dining, and local gems.
Whether you’re traveling with toddlers or great-grandparents, Jackson Hole is the kind of place that brings generations together in the best way.
📌 Planning Your Own Multigenerational Trip?
Feel free to bookmark this itinerary or DM me on Instagram (@travelingwithtorie) for tips. I’m happy to share more insights—especially how to balance activities across age groups!
For additional activities & excursion use THIS LINK!
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Post written with help from AI.