Roulette Travel Guide – 4 Days in Wyoming, Yellowstone and Grand Teton

In the years prior to this trip, I had heard the name Jackson Hole thrown around a few times in conversation – mostly in regards to epic skiing. I have sort of retired from skiing (after a long career of 5 cumulative days), so I didn’t think twice about the name. It hadn’t really come up or to mind in recent travel searches, but a cancelled trip to Colorado left a gap in my schedule and a travel itch that just had to be scratched.

Some creative Roulette searching on google flights led me to three choices for places to go in early/mid October: Greece, Costa Rica, or Jackson Hole. A childhood friend and her husband had recently taken a job assignment one town (and state over) in Driggs, Idaho, and a college fraternity brother’s father was a local there who agreed to show me around and lend some gear (and eventually bear spray). Greece would be too long of a haul for a 4 day trip, and Costa Rica had a rainy outlook at the time. Jackson Hole was the easy decision.

Trip Overview

Duration4 Days/4 Nights
FlightNY > Chicago > Denver > Jackson (20,000 points and $100)
Rental CarNational Car – AWD Ford Escape – $204
AccomodationsStayed with friends – but can be found on AirBnB for $70/night
Foodapproximately $150 including drinks
Park Admissom$ 70 -Grand Teton and Yellowstone. For $10 more, you can get an annual unlimited National Park pass.
WeatherVaried from highs in the 60’s to low’s in the teens, with some snow flurries
ItineraryDay 1 – Travel and Arrival
Day 2 – Jackson Hole
Day 3 – Yellowstone
Day 4 – Grand Teton

Approximate route beginning in Jackson > Driggs > Yellowstone > Back to Driggs > Grand Teton

In the spirit of the Roulette Mentality towards traveling, I actually did very little research other than looking at the temperature range, and trusting that I would figure it out along the way. In hindsight, I’m so thankful that I did this – because it made the trip seem like one surprise after another, figuring out each day as I went. My friend actually chuckled when I told her that I had booked a ticket to arrive there 3 days later, as flight prices can sometimes be ridiculous (more on why that is later). Fares usually average in the $400-$900 range for a round trip (but can go up to $1,500+), basic economy ticket from upstate New York into Jackson Hole (which can require up to three legs). Luckily, thanks to a healthy balance of points left over from the corporate world, I was able to get my ticket for about 25,000 points and $100 in fees. Not bad.

Packing List

Since I knew the weather and elevation could vary greatly while I was there, I had to pack for a variety of weather. Luckily, to save weight in my carry-on, my friend’s dad had an outer shell jacket for me to wear during my trip.

ClothesZip off hiking pants
Zip up fleece
Casual and Sleepwear
Hiking Gear60L Backpack
Hydration Pack
Water Filter
Emergency Bivvy
First Aid Kit
Backpack rain fly
CamerasMavic Pro Drone
Handheld Gimbal
Cold Weather GearGloves
Wool Socks
Neck Fleece
Insulated base layers
FootwearOboz hiking boots

Day 1 – Getting There

I had to pack light due to the smaller planes I would be flying in with no checked bag. Even though I had the airline card to get a free checked bag, with two connections in busy airports and a short trip, I didn’t want to risk a lost or delayed bag. To the right, you see one of the reasons I was on a smaller plane – those mountains are the Grand Tetons. Jackson Hole Airport is actually inside the Grand Teton National Park (and at an elevation over 6,000 feet). With just one runway and a terminal that resembles a log cabin, its a truly unique place to fly into.

And, when flying out, you don’t have to endure the usually painstaking TSA process, as Jackson Hole Airport is one of just 16 airports that uses private security screeners rather than TSA Agents. Anyways, enough on why Jackson was probably the best airport I’ve ever flown into. The trip was already off to a good start.

Day 2 – Exploring Jackson Hole and Driggs, Idaho

View of Jackson Hole from hike up Snow King

Despite a population of just around 10,000, Jackson Hole can swell with summer and winter tourism via the airports more than 390,000 passengers in 2018. The location between two national parks draws crowds in the summers, and the close proximity to the Teton Lodge and SnowBird and SnowKing resorts, among others, draws avid skiers in the winter. We actually hiked up to the top of Snow King, which was a nice way to get a scenic view of the city as well as get myself acclimatized to the higher altitudes quickly. Snow King is so close to downtown that you can simply park along one of the streets and walk to the beginning of the trails – they are easy to spot, as the ski trails leave clear cut outs up the side of the mountain.

View of the top of Snow King Mountain

At the top, there’s a nice little viewing platform and lodge to hang out in – we met a couple there that shared some champagne and time with their dogs before we started to head back down, and of course after sending Jenny up above for some views and video. Some bad weather was starting to roll in, and poor Jenny took some hail that made the drone drop altitude quickly, but recovered without any further issue. I took this as a sign to get back on the ground so that we could pack up and start heading down. Its a good thing we did, because it ended up nearly turning into a whiteout on the way down. Compared to the picture above just an hour earlier, you can see how quickly the weather changes.

After the hike, we arrived back downtown to wether that was clearing up, and grabbed some Thai food to warm back up. It was time to head through the Teton Pass, a treacherous road with grades up to 10%, a maximum altitude of 8,431 ft. and a regular risk of avalanche in the winter (luckily, it was still early October, but there was already snow on the ground). I ended up driving this pass several times as it was the connection between Jackson Hole and Driggs, Idaho, where I would be staying with friends. Everytime, it was a beautiful drive, although on the warmer days I wish I had sprang for a sports car on Turo, as it would have been a fun road to drive.

To get to Driggs, you had to pass through Victor, Idaho, which wasn’t that much bigger than Driggs, with a population of around 1,900 vs. 1,600 respectively (2010 census, so assume some growth there). A flat stretch of highway along the back side of the Teton range takes you eventually into Driggs. My friend noted that the apartment comple they lived in was so empty, as some people only stayed in them during the summer or winter busy times – in a complex of a few hundred townhomes, there were maybe 20-30 cars total. It was honestly a little neat to see such a small town in a sparse yet beautiful part of the country. I laid my head for the night, and got ready for the next day – where I would get to check a big one off of the national park list.

Snake Creek

Day 3 – A Long, Long Drive to Yellowstone

Now, I’m all for a scenic drive – thats why I initially intended to head to Yellowstone up through Jackson Hole and Route 191 along and through Grand Teton (so I could see the northern parts of it and just enjoy the drive – I love road trips. But, you see, I should have done the smart thing and checked the national park website for road closures – because I would soon find out that a closure would mean that I couldn’t access the park through the South Entrance. Instead – I would need to take a 3-4 hour detour, back through Idaho and into the West entrance. I mean, there are far worse places to have to take a detour. In my defense…. I have none. Shoulda checked the website.

Continuing on my way, I wound through Idaho across mostly rolling hills and non-descript little towns with just a few buildings and gas stations. I technically also checked another state off the list, as Route 20 actually passes through Montana for about an 8 mile stretch. Montana has since been scratched off of my scratch-off map, so I guess I’ll count it. If you’re looking to check off three states in one drive, there may be quicker ways to do it, but maybe none more beautiful. I had just a little bit further to go to get to the West Yellowstone entrance (where you will pay the $35 entrance fee, unless you have the unlimited pass).

From there, I wound my way through Yellowstone along route 191 – at this point, it was well past noon, and so I planned for a more scenic drive through the park and a shorter hike towards the evening. My first stop was at the Lower Geyser Basin – my first time experiencing these natural phenomenon. A pull off with a parking lot provided quick access to the walkway pictured below, which gave the otherwordly experience of walking through the clouds due to their proximity to the geysers and their steam. This pitstop took less than a half hour, and was about a mile walk along a boardwalk (highly accessible).

Next up was the Midway Geyser Basin – home of the famous Grand Prismatic Spring. Unfortunately, due to the amount and density of the steam (it was in the 40’s), it was hard to see the usually magnificent colors of the spring. But, just walking around it, you could still feel the immense size of the world’s third largest hot spring. This is another good boardwalk trail that is maybe just over a mile or so to walk most of it, with just a small section of a few steps and stairs along the way. I ended my geyser experience with a trip to see Old Faithful – and luckily, was not faced with too many crowds. You can find a plethora of info about that with a quick google search, as its one of the most famous natural wonders in the world.

I finished my day in Yellowstone with a 2 mile out and back hike to Firehole Falls along the Firehole River. In summer, it could have been a drive to the falls, but the road was closed at this time of year – and it also meant that I had the 2 mile out and back walk/hike to myself – although after later seeing some coyote on y way out, realized i might not have been as alone as I thought! Regardless, it was the perfect end to a quick but great trip into Yellowstone.

Day 4 – Grand Teton National Park

I’m going to throw a ton of pictures in here, because honestly words can’t really do this park justice. First established as a National Park in 1929, its home to the ‘youngest’ mountain range in the rockies – and ancient paleo-indian hunter-gatherer cultures. Its home to jagged peaks and glaciers, abundant wildlife (and the western hemisphere’s fastest land mammal – the pronghorn, which is capable of 70 mph), and Grand Teton’s towering peak at 13,775 feet. While not being a ’14er’ like those in Colorado, the peak does tower nearly 7,000 feet over the valley floor (where we even saw a moose on the drive in). The entire drive, I kept saying to myself that if I didn’t touch one of the mountains at some point today, my brain might not believe my eyes. I also bumped into Daniel for the second time on my trip (the previous time was by snake river) – an artist named Daniel ( who was working on a painting of the Tetons.

Since I was somewhat work out from travel and the previous few days, I chose to do an easier hike that would still give me some beautiful views of the Tetons and a decent amount of mileage without being too difficult. After some recommendations from locals and the visitors center, I decided to do the Jenny Lake hike, from the north parking lot entrance for an out and back hike. I made sure to have bear spray, as it was an area known for frequent sightings.

Overall it would have been about 3-4 miles, but I actually found a fellow hiker who was doing the loop, parked at the other end, and agreed to drive me back, and instead we did about 6 miles in a hike working its way around Jenny Lake and some smaller falls and back to the south parking lot where I caught a ride back to my car. I definitely want to come back and conquer some serious hikes in the Tetons when I have more time to spend there. The weather was a contrast from the day before, with warm and breezy temps in the 50’s and 60’s.

Final Thoughts

Overall, I really can’t think of a better place for an impromptu mountain trip for a few days. Like many of the places I visit, I would have loved a bit more time here, but I’m grateful for what I was able to get (and my friends ended up moving about a month later, so my timing was perfect). I was also able to get in between two tourists seasons, as the peak of fall was over, but it was not yet cold enough for skiing – if you hate crowds, I recommend using a similar strategy for planning your trip here. I’m confident that you will get everything you want and more from a trip here during any season of the year.

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