Back in the Saddle: A Return to Jackson, Wyoming

Zack’s Rating: ★★★★★ Ease of Travel: ★★★1/2 Wallet Friendly: ★★☆☆☆

Zack’s Reflections:

This trip was a bucket-list-style return to a longtime family tradition at the R Lazy S Dude Ranch. It marked the premier visit by the fourth generation of the Pence family, continuing a legacy that’s grown stronger with time.

My mom, Marny, served as the head wrangler of our crew and went above and beyond to spearhead this unforgettable trip. Her effort, energy, and heart made the entire experience possible.

One of our favorite memories was watching a herd of grandchildren, children, and wranglers chase Marny during a wild game of horseback hide-and-seek. The laughter was heard all the way back at the stables.

With the Tetons looming in the background, Wyoming is one of those rare places that feels both rugged and refined. From the moment we landed, we knew this would be more than just a mountain-town getaway. The mountains were majestic, and the town shared a blend of cowboy grit and high-end charm.

The centerpiece of our visit was R Lazy S Ranch, located just outside of Teton Village. Welcoming guests since 1947, it’s one of the oldest continually operating dude ranches in the region. Built on a foundation of horseback adventure and home-cooked hospitality, the ranch remains intentionally simple—no TVs, just wide-open trails and a deep sense of connection.

Trail rides carried us through herds of elk and mule deer, while evenings brought campfire cookouts and breathtaking sunsets. The cabins were rustic yet cozy, and the staff made us feel like family from day one. A special shoutout goes to the kids’ wrangler, who made this a magical experience for the younger generation.

Afternoons were often spent playing tag and hide-and-seek on horseback or trying our hand at cow penning—a ranch-style sport where riders work to separate and corral specific cattle into a pen. Don’t worry, real cowboys—your jobs are safe.

One of the highlights of ranch life was the people. We met Rob, a retired Pennsylvania State Trooper turned ballistics forensic expert, who quickly became our favorite fireside storyteller. Then there was Kevin, an active NYPD motorcycle officer, along with his wife and kids, Liam and Fiona. Liam was witty beyond his years, and Fiona owned the ranch lawn with her flawless one-handed cartwheels.

Kevin shared fly-fishing tips with Noah and generously offered to loan us his fly rod—though we all agreed we’d likely break it. Rob became our new drinking buddy, and Colonel Dryden Pence’s legendary tales made their way into the mix, adding just the right amount of storytelling to the evenings.

As for mishaps? Crawford came face to face with a moose and its baby on the trail back to her cabin—it wasn't funny for her at the time, but a story we’ll laugh about and remember forever.

Side Mission:

On one night off the ranch, my wife Natalie and my Uncle Dryden slid away to catch Muscadine Bloodline live at the Snow King Mountain concert series. From all reports, the music was great, the setting was stunning, and it added another memory to an already unforgettable week. Concert lovers, add this venue to your list.

About the Destination:

Jackson Hole is what you might call Cowboy Aspen. It boasts boutique shops, upscale restaurants, and mountain-town charm—but with at least a little grit. You’ll find antler arches, working saloons, and cowboys sharing sidewalk space with luxury SUVs.

Expect a relaxed but polished vibe. The summer weather is unbeatable—warm days, cool nights—and the town is walkable, friendly, and packed with access to Grand Teton and Yellowstone National Parks.

Getting There:

Several options are available from major hubs, but we chose to connect through Denver. As with all regional airports, it’s important to be mindful of the limited number of daily flights. Avoid booking the last connection of the day whenever possible—if that flight gets canceled, it could cost you a full day of your trip.

Flying into Jackson is a breeze—and an experience in itself. The descent offers your first dramatic views of the Tetons, and the airport is small, scenic, and easy to navigate. Flying out, however, is a different story. Things move slowly, and it almost feels intentional—no one seems to be in a rush to get you out. Crowds can build up quickly, and staffing levels often struggle to keep up.

Build in extra time when departing from Jackson Hole Airport. It’s a known hotspot for delays and cancellations, especially in the afternoons. Arrive early, pack your patience.

Where We Stayed:

R Lazy S Ranch, Teton Village – ★★★★½☆

A true Western escape at the base of the Tetons. Cozy, cabin-style lodging. Daily horseback rides. Nightly cookouts. Outstanding staff. All meals were included and absolutely amazing—we’re already planning our post-trip workout routine.

Where We Ate:

R Lazy S Ranch – ★★★★★

Every meal felt special. From BBQ to lamb lollipops and hearty soups—this was ranch dining at its finest.

Million Dollar Cowboy Steakhouse – ★★★¾☆

Slightly Upscale but not pretentious, the steakhouse delivers a refined western aesthetic—think rustic elegance with polished finishes. It’s a step up in formality from the lively Cowboy Bar upstairs, yet it still has the same frontier energy.

Signal Mountain Lodge – ★★★½☆

Perched right on the edge of Jackson Lake, Signal Mountain Lodge offers one of the most relaxing and picturesque meal settings inside Grand Teton National Park. It’s not a high‑end gourmet stop, but if you want a perfect place to unwind, enjoy the view, and a little comfort food in a stunning setting, this lodge is worth it.

Where We Drank:

Mangy Moose, Teton Village – ★★★★☆

A local favorite that blends après-ski energy with laid-back summer charm. Great cocktails, famous sloshies, and hearty bites like burgers and chili. The patio has a killer Teton view, and there’s often live music. Casual, lively, and worth the stop.

The Handle Bar at Four Seasons – ★★★★☆

Upscale bar meets rugged surroundings. Great cocktails, elevated pub food, and a spacious outdoor patio with mountain views. It’s a classy way to unwind in Teton Village.

Million Dollar Cowboy Saloon – ★★★☆☆

Definitely more of a bucket list spot than a hangout. Sit in a saddle-shaped barstool, grab a drink, and check it off your Jackson list. Tourist trap, but a must-do. One drink, check the box, move on.

Activities and Attractions:

Concerts at Snow King – ★★★★☆

Beautiful setting for live music. Family-friendly, relaxing, and scenic.

Whitewater Rafting on the Snake River (Lewis & Clark Expeditions) – ★★★★☆

One of the trip highlights. The crew was fantastic and our guide, Luke, made it even better—funny, knowledgeable, and local. The views along the Snake River were stunning, and we spotted three bald eagles. The rapids were thrilling but family-friendly. Highly recommend this local outfitter.

Fly Fishing on the Snake River (Teton Scenic Floats & Fly Fishing) – ★★★¾☆

Josh, our guide, was great—knowledgeable, funny, and great with kids. The boat setup was comfortable and the scenery top-notch. That said, if you’re expecting to catch a bunch, temper your expectations. The Snake’s native trout are picky. Still, the bonding time with my son made it all worth it.

Jackson Hole Rodeo – ★★★☆☆

Classic Wyoming. Great for first-timers and families. If you’re a big fan of the sport, you might be underwhelmed by the overall competition level—but as long as you don’t expect Cheyenne, you’ll have a great time.

Unique Stops:

Kemo Sabe

Luxury western gear and custom hats. High-end cowboy fashion.

Made Gift Shop

Great for handmade souvenirs and local artisan finds.

Teton Gravity Research

Action-sports vibes. Cool merch and adrenaline-laced energy.

Travel Tips:

Pack the bug spray. Mosquitoes don’t mess around in the summer.

Teach your kids about wildlife. Elk, moose, even bears—these animals aren’t just in the parks. Help your kids know how to act if they spot one.

Bring a good hat. Whether cowboy or city-style, a hat is a must. (P.S. Rafter M Hat Co. can help you find the perfect one.)

Plan extra time at the airport. It’s gorgeous—but chaotic. Pad your schedule.

Final Thoughts:

Our time in Jackson Hole and at R Lazy S Ranch was more than just a vacation—it was a reconnection to nature, family, and a simpler rhythm of life. Between the horseback adventures, fly fishing on the Snake, sunset campfires, and impromptu moose encounters, we left with full hearts and dusty boots.

Jackson has a way of staying with you. It’s wild, yet welcoming. Sophisticated, yet soulful. Whether you’re wrangling cattle or sipping cocktails under the Tetons, you feel grounded here—anchored by the land, the people, and the stories shared around the fire.

We came for a family tradition. We left with new friendships, unforgettable memories, and a plan to return.