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Roundtrip from Seattle DT to Mt Rainier (Tolmie Peak) ?

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I have a friend visiting and would like to do the Tolmie Peak hike:
Google Maps

I'm starting from DT Seattle, in a Model 3 LR RWD (330 miles). Round trip to Mt Rainier and back says 150miles, even with phantom drain and energy loss, I'm assuming I can do this trip easily.. but still have some concerns.

Do you guys think there's anything to even worry about?
 
You'll be totally fine. There's even a supercharger in Auburn, which is about halfway to the trailhead. Give yourself some margin if you're uncomfortable, but the navigation in the car takes elevation into account. If you start at 100% in Seattle, you probably won't need to charge at all, but the Auburn supercharger will be a nice backup.
 
While you will likely be sweating it as you near the top, you will make up for it on the way down. I can’t imagine you would actually have a problem. I have climbed many a mountain in mine and yes I have driven as many as 8 hours on a charge.

I know regen breaking will be big coming down 5000ft... what kind of regen should I expect?

For example, should I expect to end up at 0 ft with range gained.. or just the same as I started from the top?
 
For example, should I expect to end up at 0 ft with range gained.. or just the same as I started from the top?
Not at all sure what you mean by this question, but you won't have any trouble making this trip at all. The Auburn supercharger is there on the way back if necessary, but it won't be.

I drove my degraded S100D from North Seattle to Sunrise to Paradise and then back to North Seattle last week on one charge and it wasn't even charged to 100%. I started with something like 308 Rated Miles and got home with over 20 left. I even made a wrong turn on the way home which cost me a couple miles, and I had the A/C blasting the whole way. I had planned to stop at the Auburn supercharger on the way back, but I didn't need to so I just went straight home.
 
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Here's the data at the end of that trip (Remember this is a Model S so your wh/mi will actually be lower, but the use of rated miles should be roughly the same):

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5FE00E08-305D-405A-BF16-576FD99750BB.jpeg
 
I drove from South Seattle up to Paradise in my SR+ (240 mi) and back, so I'm sure you'll be fine in the LR. I gained about 12 - 15 mi of charge dropping down from Paradise to the entrance of the park. I got close to empty when I was done with the trip (188 mi trip) but there's always Auburn (like others have said) if you start to worry.