Spokane to Omak, over the pass to Twisp, then south to Wenatchee, in the winter. Will you make it?
I checked with ABRP and my car can make the trip. I would plan to stop in Entiat and top off the battery at the Tesla Supercharger there.
https://abetterrouteplanner.com/
According to Plugshare, Omak has multiple "level 2" chargers. Depending on what you were planning to do in Omak, you might be able to plug in your car for a few hours... if you are spending the night, odds are good you could charge your car fully.
You chose this route well as a tough test. ABRP says my car should start by charging at the Spokane Supercharger station to 96% state of charge, and could make it all the way to Wenatchee with 14% charge left, no charging stops along the way. But you specified winter, and I'm sure that eats up the 14% margin and more. But the Supercharger in Entiat should make it work.
Note that Wenatchee is also not great for Teslas. There is no Supercharger in Wenatchee. If you have the CCS adapter, you could maybe fast charge that way, but the CCS adapter is expensive and I have no plans to buy one. (My car would need an upgrade before I could use it, making it even more expensive.)
If you are spending the night in Wenatchee, it shouldn't be any problem, you can use a level 2 charger and the charge should be done before morning. Note that you can charge a Tesla anywhere by plugging into an ordinary 120V outlet... but in winter, it may not charge fast or at all. But 240V charging works even in winter.
Both Winthrop and Chelan have options for level 2 charging, including some Tesla "Destination Chargers". Twisp has a CCS charger, another place you could use the CCS Adapter if you have it.
If you are heading west, there's a Supercharger station in Leavenworth. (I've used it!) If you are planning to get onto I-90 there are multiple Supercharger stations on that. Even in winter, travel on I-90 is easy.
Your proposed trip is an example of a trip that is possible, but marginal. If it's something you plan to do a lot, you might be better served with a combustion car, at least until Tesla builds a few more Supercharger stations.
If I were doing this I'd make sure to pack my Tesla mobile connector charger. In the worst case, find an RV park with 240V power and pay them to use it for a few hours.
Looking at the map, I'd say that Omak would be an excellent place to add a Supercharger station. It would be a nice midpoint between Spokane, Entiat, and the nearest Supercharger to the north (over the border, in Canada, a place called Osoyoos).
If I could add two, I'd add Republic, WA.
But really I wish for three: Omak, Republic, and Coulee Dam. There should be Superchargers right next to the Grand Coulee Dam.
Ah! For completeness, I checked the Tesla web site to see if they are promising any Supercharger stations that would help with your winter tour. It says that in 2024, a new Supercharger station should open in Okanagan.
It really is just a matter of time until Supercharger stations are connected up enough that even a winter tour of the northeast corner of Washington state will be easy.
When I first got a Tesla, it was a challenge for me even to drive to Mount Rainier and back. But now there's a Supercharger in Auburn and it's not remotely hard. The more time goes by, the better connected the charging network will get, everywhere.
P.S. I found the Okanagan Supercharger by looking at the map on the Tesla page. I checked the list of Superchargers and it's not in the list, not even as a "coming later". I also checked https://supercharge.info/ and it didn't have anything yet about Okanogan.