As a holiday gift, we planned a special getaway to Jackson Hole for my wife's parents. Not long after, I decided to do the same for my parents, except to Belize. Around the same time, we got invited to a destination wedding in Todos Santos, Mexico. Since we’re based in Costa Rica and flights to the U.S. aren't exactly budget-friendly, we decided to stack the trips back-to-back-to-back. Wild? Yes. But it totally worked. First leg of the journey: Jackson Hole, Wyoming.
Our travel dates revolved around the wedding, which landed our Jackson Hole visit in April, prime shoulder season. Our crew isn’t into skiing, so we weren’t chasing powder, but it also wasn’t quite summer hike season. Even so, we found plenty to love during this off-peak window in Jackson.
Where We Stayed in Jackson Hole
We booked a cozy cabin that struck the perfect balance between town and Grand Teton National Park. The space could technically sleep six adults, though four of us (plus baby Marin) felt just right. Each day we woke up to breathtaking Teton views and elk casually grazing in the backyard. Not bad.
What to Do in Jackson Hole During Shoulder Season
🦌 Ride Through the National Elk Refuge
The elk tour was a highlight. Because most of the snow had melted, we rode in a horse-drawn wagon instead of a sleigh, but it was still magical. The guide shared fascinating insights, and we were surrounded by hundreds of elk. An unforgettable wildlife experience.
🚡 Visit Teton Village
While known for its ski scene, Teton Village also boasts great restaurants and boutique shopping. We had lunch at The Handle Bar inside the Four Seasons a surprisingly relaxed and welcoming pub despite its posh location. Unfortunately, the gondola was closed due to the season. One of those shoulder-season tradeoffs.
🎨 Stop by the National Museum of Wildlife Art & Visitor Center
The art museum features stunning outdoor sculptures and a beautiful overlook. Definitely worth pulling over for a quick wander. And surprisingly, the Visitor Center had some really fun exhibits for toddlers Marin loved it!
🏞 Explore Grand Teton National Park
This is what Jackson Hole is all about. Even in April, the snow-covered landscapes were jaw-dropping. Sunny skies and mild temps made it easy to explore, although some trails were still closed. Still, the park in shoulder season has a peaceful, untouched beauty that’s hard to beat.
🍸 Hit the Town (Bar-Style)
The Million Dollar Cowboy Bar is iconic with saddle barstools and a Western-themed gift shop. We also stumbled upon a free music fest downtown and ended up catching a great band at the Silver Dollar Bar in the historic Wort Hotel.
🐾 Go Wildlife Spotting
Driving through the park at sunrise and sunset gave us our best chance to spot animals. We saw tons of elk, and after much searching, two majestic moose. Worth every minute.
🛍 Browse Local Boutiques
Jackson’s town square is packed with charming shops. We picked up a baby onesie for Hobie and matching PJs for the boys. I was this close to buying Marin cowboy boots… but figured they’d be outgrown in weeks (plus: Costa Rica = barefoot life).
Where to Eat in Jackson Hole
Glorietta Trattoria: Beautiful interior, handmade pasta, and an unforgettable meal.
Persephone Bakery: The perfect brunch stop with great coffee and a cozy atmosphere.
The Handle Bar (Four Seasons): Don’t be intimidated, it’s kid-friendly and comfy.
Cowboy Coffee Co.: Stop here for your morning fuel and a warm pastry.
The Local: Great food with a casual bar side that’s ideal if dining with toddlers.
Is Jackson Hole Toddler-Approved?
Yes! Our Jackson Hole trip was a blast for the whole family. Marin loved seeing wildlife, playing in the snow near our cabin, and running around the parks. While the dining and shopping scene is definitely more adult-centric, there’s enough outdoor fun and relaxed activities to keep little ones entertained. Just keep in mind: If you’re hoping to explore the parks, be ready for some long drives.
"A version of this guide is also available at Gypsy Sols Travel and Lifestyle."
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Grant Davis is an entrepreneur, devoted dad, and beach lover focused on purposeful, intentional living. As the founder of Bright Futures Counseling and Gypsy Sols Travel and Lifestyle Design, he combines empathy with business savvy to help others reduce stress, increase impact, and create fulfilling lives.
Grant started his journey supporting school counselors in managing workload and gaining recognition through practical strategies. With Gypsy Sols, he shares his and his partner’s story of leaving traditional careers to pursue travel, freedom, and sustainable income, encouraging others to live intentionally today.
Driven by a commitment to empowerment, Grant helps people design lives that reflect their values and passions, proving meaningful change is possible with the right mindset and action.