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I think he failed to appreciate the 80A charger at the base of the mountain.

He clearly made a rookie mistake not using the CS90 Clipper creek charger. Keep in mind we were all rookies at some point.

Um, aren't they talking about using the CS-90 here?

2:50 p.m.: Arrive at the Mt. Washington Auto Road Welcome Center with 37 percent battery, not 47 percent. We get a charge off a Level 2 station that usually charges the center’s Smart Car, pictured above wrapped in the glorious vistas of Mt. Washington State Park. It’s a little faster than the Indian Head Resort charger, but it won’t get us where we need to be for this to be our last stop. +100 to range anxiety. We’re off the chart, people.

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This Tesla (barely) climbed Mt. Washington - News and reviews - Boston.com

I do believe a Supercharger in Northern New Hampshire would solve the problem, somewhere at the Junction of 16 & 302. People do just day trips. Frankly, I do believe he tested insane mode several times....
St Johnsbury (I91/I93 junction) would be good, too. I know several people who prefer to go straight up I91 to A-10 for the CT to Montreal run.
 
Climbing Mt Washington is a pretty tough challenge as it's out of the way, requires a lot of energy, and is often done as a very short up and back trip. This seems like a general, but hopefully temporary problem. The Superchargers are being installed on major travel routes which makes a lot of sense, but leaves a lot of holes for vacation destinations, e.g. camping, skiing, beaches which are a day trip and/or there's no destination charging. For the time being such trips take some planning and are not very convenient.

What I'm hoping is that after 2016 Tesla will have enough major routes covered that they can continue by filling in the holes in the map. IMHO, if they really are planning on building a mass market Model 3, that will be a make or break requirement.

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This Tesla (barely) climbed Mt. Washington - News and reviews - Boston.com

I do believe a Supercharger in Northern New Hampshire would solve the problem, somewhere at the Junction of 16 & 302. People do just day trips. Frankly, I do believe he tested insane mode several times....
It's 133 miles from the Hooksett Rest Area to the top of Mt Washington, so even ignoring the altitude gain, it's not really a practical round trip without a few hours of level 2 charging.