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Devil's Advocate

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I'm rather familiar with Western Amtrak service but not with the Empire Builder route specifically.  Is there a particular season and/or direction that's more advantageous than the others?  What about doing something like a PDX-SPK-SEA run instead of CHI-SEA/PDX?  Are there any predictable PV options on this route?  What are the best stopovers with regard to easy access to local transportation and natural beauty?  Is there a hotel that looks/feels like a visit to "The Shining" anywhere near the Going to the Sun Road area?
 
Going east is the way to go.   You go through Glacier during the day that way. But your two trips don't really match up.

What about PDX-SPK-SEA-CHI?   That why you get the best if everything.   I only rode once SEA to CHI.   I will be returning this year but riding the gorge on my bike then up over Mt Hood back to PDX.   Catch the train to Olympia.  So I will get to see the best part of the gorge but on a bicycle.  Something still tells me that by train on the EB the leaving from SEA is the better of the two.   With the SEA route you get the Puget Sound  and the Cascades. 

The opening scenes of The Shining was filmed in the gorge.  The outside scenes of the hotel was the Timberline Lodge on Mt Hood.

The Price of Wales in the Glacier Park area has the same feel to it.

https://www.glacierparkcollection.com/lodging/prince-of-wales-hotel/

Way up in Alberta though.

The hotel at Many Glacier is pretty close.

Edit:   so sorry you want  to head east on the EB.   My dyslexia strikes again.   Corrected above.
 
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One of the more spectacular things encountered on the EB between CHI and SEA is the Cascade Tunnel.  Other than being in darkness during the 7.8 mile trip through it, there's nothing much visually spectacular about it from the train.  However, it is somewhat mind-numbing (to me at least) to realize that when passing under the peak of Cowboy Mountain about 2 1/3 miles from the West portal, you're under about 3280 feet of solid granite.

To me, the most visually spectacular part of the trip is the sheer vastness of the  plains of central Montana.  I've taken the EB both ways about six times total and I still marvel at that view of Big Sky Country from the train.   
 
This New Englander is a fan of the Cascades SPK-SEA AND the Columbia River SPK-PDX.  Both have fantastic scenery.  I've done both perhaps 10+ times each, mostly eastbound.  I did #28 last April and will be on #27 this April.  Next year, Seattle will be my 'target' city.  I recommend both!

As for a PDX-SPK-SEA 'triangle' trip, you're cutting it VERY close at Spokane if you plan on getting off #28 from PDX and boarding #7 to SEA a few minutes later.  I'm crazy enough to expect #7/27 to be running an hour late so it's worth a shot for me.  For the faint of heart, an overnight at SPK would be recommended and rent a car the next day to tour the area.
 
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East bound has more wiggle room to seeing Glacier in daylight. The schedule puts it through in the early morning (8:15ish and for the next 1.5 hours), so you’d have to be pretty late to miss Glacier eastbound. West bound, the schedule is 6:45 pm, so depending on the time of year an hour or two delay and you miss Glacier entirely.
 
We are traveling west in May, getting off/on the train in Whitefish. I'm excited that we get into Whitefish within a couple of minutes of sunset and leave there at 7:40 so we'll be awake for Montana coming/going in daylight.
 
Headed eastbound, you get Glacier in the morning but the Gorge or WA Cascades in darkness. Westbound, it’s the opposite.

You can’t do PDX-SPK-SEA due to timing, but you can do SEA-SPK-PDX as a same day trip! You can even do a PDX-SEA connection beforehand. I’ve done it.
 
Last trip I had plenty of daylight pretty much all the way to Levanworth from Seattle.   My trip was in September and as I recall left at least a half hour late.

.
 
One of the more spectacular things encountered on the EB between CHI and SEA is the Cascade Tunnel.  Other than being in darkness during the 7.8 mile trip through it, there's nothing much visually spectacular about it from the train.  However, it is somewhat mind-numbing (to me at least) to realize that when passing under the peak of Cowboy Mountain about 2 1/3 miles from the West portal, you're under about 3280 feet of solid granite.

To me, the most visually spectacular part of the trip is the sheer vastness of the  plains of central Montana.  I've taken the EB both ways about six times total and I still marvel at that view of Big Sky Country from the train.   
I agree with you on the vastness of Montana. Some people find it boring. I find it to be an amazing landscape.
 
I sit there and wonder how long it takes the rancher to get from his house all the way to the other side of his property.  ;)
 
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