Jetsetting to Jackson Hole

the destinations of distinction blog

I’d almost forgot what a 4am alarm felt like. So many years of traveling internationally where the flight would be taking off at 8am, but it took you over an hour+ to get to the airport; never mind the 2 hour window, prior to departure, they recommend you check in for your flight.

So here I am, heading back to the jetway for a long awaited adventure. My last FAM (familiarization) work trip was to Jackson Hole back in Feb so it’s fitting that my first FAM post-pandemic is back to Jackson Hole.

It’s raining as we pull up to the terminal which seems like the perfect compass, pointing me towards the crisp & clean mountain air.

Although the airport is nothing like its normal bustle, it’s admittedly more busy than when I took my quick trip to Florida in June. If you want to know more about that travel experience + what it was like at Universal Studios, check out my Vlog here.

Years ago I signed myself up for Global Entry + Clear.

It felt as if I floated through TSA like literal breeze. The Clear machine scanned my eyes & all I needed to do was walk up to the bag check. No showing of ID or second scan by the TSA agent. Trust me this is an investment worth looking into for the sheer convenience. For more info on Clear, click here

I’m glaringly aware that I’ve overpacked. Something I advocate against in our most recent blog, found here. Truth is…your girl is rusty & the weather this time of the year in Jackson Hole fluctuates from 55F in the day to 20F at night. Layers are necessary plus jackets, hats, gloves, boots. So with my carry-on + personal bag bulging, I made my way through bag check into the familiar face of Terminal C.

Once I made my way through to the gates, I was excited to see some of the eateries were now open. Markings between chairs were prominent & spaced. I had about 45 minutes until boarding so I grabbed a cup of coffee & relaxed until boarding. 

Boarding was quick & in full transparency I don’t miss the pre-formed lines by group number that would inevitably start forming around 30 minutes prior to boarding. It always reminded me of herding cattle & the space was TIGHT.

Now, there are no lines ropes off by group. No one hoards around the ticketing desk this morning as most of seated with a few standing on the outskirts of the boarding area. I flew United (my airline of convenience as their main hub is out of EWR Newark). United does not space seating & boards from the back of the plan forward now just an FYI. They do send a pre-flight notification to passengers alerting them that the flight is anticipated to be full & you have the choice to switch your flight at no charge. 

On board the service is limited but I did appreciate the pre-packaged snack items with sanitizer wipe. Food service has notoriously gone downhill on many airlines over the years so who knows what service might evolve into as we move ahead into 2021 & beyond.

The rest of this blog is dedicated to featuring all the highlighted activities of our trip with a full review of our host hotel, Hotel Jackson. Grab a cup of coffee & scroll down!

Day of arrival: Kristal & I arrived 24 hours ahead of the group. I always do this on any FAM trip. It’s important for us to be in the destination & ready to welcome our guests on their arrival. It also gives us the chance to run through any last minute itinerary changes, room checks, etc. how important are FAM trips you ask? Take a look here.

Jackson Hole is truly magical. The destination changes with the seasons & depending on when you set foot against the mountainous backdrop, you will have a very different experience each time. We traveled in October, so the weather (as mentioned above) fluctuated. My faux fur vest & scarf came in handy during the chilly nights but could easily be removed for daytime activites.

If you’re going to stay in Town Square, the best choice for elevated accommodations is Hotel Jackson. Call us biased but you won’t find another 5* hotel in the area unless you head towards JHMR (Jackson Hole Mountain Resort).

Our week was jam packed & the activities didn’t disappoint. We also sampled some super tasty food + delicious cocktails. For our foodie followers, Kristal will be doing a full review & ranking of all the places we tried so check back soon.

Our first day was all about Jackson Hole Wildlife Safaris. This is a fantastic guided tour consisting of true local experience. Here we traveled along the southern park roads watching for wildlife and stopping frequently for photo-ops. We saw places like antelope flats, the small town of Kelly and views of several mountain ranges that form the valley of Jackson Hole. Jackson Hole’s wintering wildlife is abundant with opportunities to see bison, elk, deer, moose, fox, coyote, bald eagle, trumpeter swans, and if you’re lucky, wolves.

We got lucky right off the bat & were greeted by some moose!

Next we made a beeline for a “610” sighting. 610 is the tag-name given to a Grizzly momma who happens to have 2 cubs. We got extra lucky & spotted her roaming the valley. To be this close to a grizzly bear is incredible (and a bit scary)!

As we made our way through the winding roads, it would have been an opportunity missed not to get some fun photo-ops in…

The above pic was taken at Jenny Lake. It felt as if I dove head first into a Bob Ross painting. Apparently this is a very popular stop off point for photos so we felt v VIP to snag these fun pics.

Lastly, it was a stop off right on the side of the road…because…well mountains!

That night we indulged in some fantastic food in town & HAD to stop off at the Cowboy Bar. For those that don’t know, The Million Dollar Cowboy Bar is Wyoming’s landmark watering hole & located on the town square in the heart of Jackson. 

The Million Dollar Cowboy Bar is a unique Western drinking and entertainment venue that was established in 1937. True to its name, the Million Dollar Cowboy Bar is no ordinary bar. Countless celebrities, presidents, royalty, cowhands, as well as people from all walks of life, have enjoyed great fun within the walls of the iconic Million Dollar Cowboy Bar.

The Million Dollar Cowboy Bar is internationally famous for its western dancing and live entertainment. Some of the finest entertainers in the country western scene have been known to take the stage here, including Waylon Jennings, Hank Williams Jr., Asleep at the Wheel, Hoyt Axton, Glen Campbell, Tanya Tucker, Willie Nelson, Commander Cody, and the James Cotton Blues Band. Nowadays, The Cowboy provides seven days a week of live music and continues to feature local and nationally recognized bands.

The next day we were off for a 1/2 day hiking experience with Hole Hiking Experience. Our guide Cathy was a full-force of knowledge as we Hiked to the top of Munger Mountain. The full trail takes you just over 5 miles & the views at the top are worth every burned calorie. Pro-tip: If you suffer from asthma like me BRING YOUR INHALER. The flora & fauna is stunning but depending on the season it can wreak havoc on your lungs.

Next up it was time for some stargazing with Wyoming Stargazing. We ventured out into the blistering cold (30F)! to an open (and very dark) field. The high elevation in Jackson Hole (6,500ft on the valley floor) where we stargazed, means that we looked through much less atmosphere than at sea level. Making the night sky clear as glass.

We sipped on wine while wrapped in blankets & were each given an iPad to explore the night sky. Speaking of, I pre-downloaded the Night Sky app on my iPhone & would HIGHLY recommend it to anyone even slightly interested in astronomy. I feel like I’ve finally learned something about the night sky, constellations, planets & quite a few in the group saw shooting stars.

Possibly my favorite experience of the trip was the custom hat making experience with Crown + Brim. This bespoke & private experience is led by the shop’s founder, Sarah Kjorstad. Sarah is a multi-generational Wyoming girl, growing up on a ranch in eastern Wyoming. Her hats, and the passion that fuels their creation, are a reflection of her classic style and cowboy heritage.

As we meandered around her shop trying on the various custom styles, it was apparent just how passionate Sarah is about her work. She was eager to help us all find a hat that expressed our character & personality. Some of us opted for simple leather accents & vintage ribbons, while others chose feathers & hand-beaded hat bands. We had so much fun & it was a special treat to have a look into her workshop where she literally sets her hats on fire!

I’m anxiously awaiting my hat’s arrival (custom orders can take up to 6 weeks). I plan on doing a full unboxing so more to come!

Krisal & I finished out our week staying for 1 night at the Four Seasons in Teton Village. The true benefit of this area lies in the winter season. It’s ideal for families & friends who truly love the ski-in/ski-out concept. While it was interesting to see the slopes bare, the backdrop was still breathtaking & we enjoyed a glass of bubbles fireside to cap off the amazing week in Jackson Hole.

Pro-tip: Four Seasons has the tastiest elk chili + they make homemade bison jerky in-house. INSANE! More on that in Kristal’s food blog coming soon.

Want to learn more about our trip? Check out our vlog here! We also documented the entire trip on our IG storyline! Click here & head to our first highlight bubble to re-live our experience 🙂

Until next time, Pack Light & Travel Deep!





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So here I am, heading back to the jetway for a long awaited adventure. My last FAM (familiarization) work trip was to Jackson Hole back in Feb so it’s fitting that my first FAM post-pandemic is back to Jackson Hole.

Jetsetting to Jackson Hole