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San Jose to Kirkwood Mountain Resort Charge Plan 70D

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Can't help you at Kirkwood, but for the rest:

Depends on the route you take up there. I drive up to South Lake frequently (from the peninsula) with an 85D. I have to stop in Barstow on the way up there for sure, no way I could make it otherwise. On the way back I can make it from South Lake home on a single 90% charge., Maybe even less and I drive 75mph or so.

There are Superchargers up there now in South Lake I believe at the Hard Rock.

That Kirkwood drive during the warmer months is really a beautiful drive and during the fall when the leaves are changing, breathtaking.
 
Will be much easier when the "planned for 2018" Supercharger opens there.

Per Plugshare there are now 6 80A Tesla connectors there and 2 40A Clipper Creeks (although the last comment indicates that only 3 of the HPWCs are working but that's inconsequential as they're mounted in a location where it would be impossible for 8 cars to charge at the same time).

From San Jose I think your best bet is a 100% charge at Manteca and assume you'll need to juice up on one of the L2 chargers before you leave.

I can't imagine the chargers being highly used in the winter.