My solo snowboard trip to Big Sky
Highlights and tips from a Montana 🏂 adventure
Montana, for me, was always this place at the top and sort of middle of the U.S., untouched and raw in a perpetual natural state.
It had never really been on my travel radar…until two developments over the past 7 years: being a Yellowstone fan, and getting more serious about snowboarding.
Sure, I’d seen friends document their Montana trips in vlogs, but their POVs were as “strangers in a strange land” where rural places still seemed inaccessible to outsiders, so I remained aloof.
Content entrepreneur | Agency Founder & CEO | Bestselling author Featured in Forbes, Wall Street Journal, Business Insider, Bankrate, Cheddar TV, HuffPost | Join more than 2,500 people who follow Shindy’s unconventional lifestyle, travel, and career advice:
But then, as one of approximately 5 million weekly Yellowstone viewers, I too, became enamored with Taylor Sheridan’s American pastoral soap opera about the Dutton family’s saga to preserve land and protect family at all costs.
Perhaps what the show does even better at is advertising for Montana, showing off landscapes and vistas that would make anyone tap their inner cowgirl.
After all, I grew up in the south, and I’m a walking duality: I’m city and country; a little Four Seasons, a little redneck; I like black tie galas and line dancing; I like cheesy pop music and metal; I like eating at hole in the wall places and Michelin restaurants.
The New York Times described Big Sky as “sprawling, luxurious, and pricey. And maybe the future of skiing.”
Naturally, luxe mountain vibes definitely spoke to me.
As I planned my solo snowboard trip to Jackson Hole, I also came across this article which proposed taking an “unforgettable” and “once in a lifetime” trip to explore both Jackson Hole and Big Sky.
My Ikon Pass would grant me up to 7 days at both mountains, consistently rated as some of the top ski mountain destinations in the U.S.
And because I was already renting a car, I figured why not?
Part of the reason this trip took a ton of planning and logistics was the planning of not just one but two accommodations in Jackson and then Big Sky, and then also getting to both places and back in one piece, with a dog.
In the end though, it was totally worth it.
Here’s how I traveled on my solo snowboard adventure to Big Sky, Montana.
Highlights of my snowboard adventure in Big Sky
How I got there
From Jackson Hole, Bean and I set out on a sunny late morning road trip in our Hertz-rented RAV4 to Montana.
We drove through Idaho and the western border of Yellowstone National Park.
We knew a snowstorm was making its way to Big Sky in the evening, so we wanted to arrive before dark.
The total journey was 175 miles, or about 4 hours, including a stop at Wydaho Coffee Roasters in Driggs, Idaho, about 40 minutes in, and another for gas.
Along the way, we saw expansive, snow-covered fields and mountains, and weather changes from sunny and mild to cloudy and cold.
Road conditions were clear through most of Wyoming and Idaho, until the very last hour into Montana, which became downright icy and treacherous.
If you’re planning on driving this same trip, I’d recommend an AWD or 4WD car or truck, and have some experience driving in snowy or icy conditions; we slipped and skidded a couple of times on single-lane, ascending mountain roads.
But if you stay calm, drive slowly, look ahead, and know what you’re doing, then it should be less of a white knuckle experience.
Where I stayed
I took advantage of a special discounted launch price to book at Wander’s Big Sky Basin, located a short 10-minute drive from Big Sky ski resort.
If you're unfamiliar with Wander homes, then consider them to be kitted out AirBnb homes.
Tiktok failed to load.Enable 3rd party cookies or use another browser
One huge draw is a full workstation setup, complete with ultrawide monitor and (usually) a microphone and webcam, though our house didn’t include these.
These “smart-enabled” homes also often offer full gyms and Peloton bikes, and some properties even include a Tesla for use.
Our property wasn’t quite ready because some of the advertised amenities were either missing or weren’t set up, but the concierge did the best they could to make things right.
That said, the house was among other new construction properties located at the end of a cul de sac and the target market is clear: modern, tech-enabled, and affluent adventure seekers.
Lodging alternatives
Because I booked the Wander home early on, I didn’t really search for other options, however I saw a number of private condos, villas, and hotels for rent in the Moonlight Basin and Spanish Peaks areas among properties managed by the resort itself.
For hotel resorts, consider the Montage, and rumor has it a new One & Only will also be opening in 2025.
There's also a lot of new construction happening for high-end mountain homes, so there will be even more opportunities for luxury rentals in the future.
How I got around town
Big Sky resort itself is fairly small; the village is walkable from one end to the other in under 10 minutes.
The village comprises restaurants and gear shops, with one main central building, The Exchange, that offers branded merch, restaurants, and a small grocery store.
For riders, the shop in town is The Rider’s Room, where I purchased replacement gloves for a lost mitten somewhere in Jackson Hole.
How I got around the mountain
Getting to the resort by car is easy. The best part? Free daily parking, with a shuttle that takes you from the lot to the main Mountain Village.
Like Jackson, I booked group lessons for an intro to the mountain and to get familiarized.
My guide was a southern gal from Greenville, South Carolina, and my group lesson ended up being a private lesson—love when that happens.
How I shipped my gear
Just like how I shipped my gear out, at the end of our trip it was time to ship my gear back with ShipSkis.
We visited Big Sky Print & Ship where we printed our ShipSkis labels and dropped off our gear for pickup.
General observations
If you’ve heard Big Sky is rocky, you heard right. In early February snowfall was scarce leading up to my trip; the result was rocky surfaces on some runs which can be downright dangerous.
Luckily the conditions turned just as I arrived and I experienced some super fun powder and some of the widest, uncrowded, and most expansive runs I’ve ever experienced.
In fact, I wish I’d spent more time here exploring all the runs; a few days and you’ll only see a fraction of what’s here.
The Andesite Mountain area alone is massive; next time I’ll dedicate a week.
If it interests you, here were my costs and what to expect for a ski or snowboard adventure at Big Sky:
Airfare: Varies depending on origin and flight class, fly into Bozeman Yellowstone Airport (BZN)
Wander: $545/night intro offer (now listed at $1,333/night). This link gives you $250 off a new booking
Ikon Pass: An annual Ikon Pass is $1,249 and renews for a little less; it gives you 7 days at Big Sky; this is totally worth purchasing if you are spending a few days here and anywhere else managed by Ikon. This is because daily lift tickets at bigskyresort.com can go upward of $400; prices vary (~$250 to $480) by demand and time of the season
Group lessons: Big Sky offers group lessons starting around $335 and you can book onsite
Hertz rental car: $261 (for 10 days)
Gear shipping: Sending my gear home on ShipSkis cost $147. This link gives you $10 off your next shipment
Next up: New York (as a tourist, no longer a resident)
Visiting New York City as a tourist and former resident is a novel experience, almost like riding “the amusement park of New York,” as my friend, former longtime New Yorker and casting agent Aaron Bakalar once described.
And you can read all about my whirlwind return to the big apple in next week’s newsletter.
**
Until next time,
Shindy
On Instagram + TikTok
***
Like it
Did you enjoy this newsletter?
Please like it by clicking on the ❤️ at the very top or bottom of this post.
Referral Rewards
When you share my newsletter with someone you think would find value in it, that is the greatest gift. 🙏
But now, if you refer once, twice, or thrice, then I’m rewarding you with Instagram shoutouts, personalized notes, and Zoom chats for up to 30 minutes on any of the following topics: your content marketing efforts, a work problem and how to solve it, how to write or edit better, a frank opinion about your social media branding, a style or brand consult, travel tips, and anything else you want to gab about.
Your writing has a way of making us feel that we are on the journey. It’s so fascinating, interesting, informative, magical, and inspiring.
You’re so adventurous and organized.
Bean is a lucky boy! I cannot wait to read about NYC next week!!!!! This was FANTASTIC!!!!❣️❣️❣️