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100D Roadtrip Idea - Entire Natchez Trace on one charge (440 miles), speed limit 50mph

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Map of the route
Speed Limit

According to plugshare, there are public chargers very near both ends of the Natchez Trace. According to Tesla's website, a 100D can travel 468 miles at 50mph and 70 degrees without climate control.

This would be a great drive for someone to attempt without charging.

Bonus points if it can be done 100% with autopilot.
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From a technical standpoint, it may be possible, but probably at a lower speed than 50 MPH. Elevation changes, traffic conditions (maintaining constant speed) and weather (rain, snow, temperature, wind) could also have a significant impact on range.

You should also assume you'll only use 90-95% of the charge, and not risking damaging the battery pack by depleting it too far.
There are a lot of elevation changes, but, it's a net 1,000 feet change. From Nashville, it's essentially downhill. I've thought about it as I live about 5 miles from the start in Nashville. Would be better to get 10 100D drivers to do it in an AutoPilot convoy and take turns drafting like a bicycle peloton. That would make it a no brainer to get all the way there.
That would be a beautiful drive! I've driven a great deal of it, and it can be very nice. It's been a good while, but I recall that traffic typically is fairly light and easy to deal with (due to the highly enforced, low speed limit).

Now, should something go awry, are there any spots along the way where you can bail out for an emergency charge?
Charging options are sparse. There are chargers just off route in Tupelo, MS which is approximately mid-way, but that defeats the challenge of one charge.

There are also chargers in Jackson, MS for an emergency top-off (if going north to south).
I’m new here, so if I do something incorrect, please let me know and be gentle.

I too have had this idea for a while. I even made a nice proposal/presentation.

Frankly, this is doable and should be done NOW!

The timing is right and I would like to be involved consulting and making simple suggestions:

1) The whole idea so far presented would be fine, but it includes too many roadblocks to success
a) What people see and how it’s produced are two different things, perception is that a sellable product does the prescribed course. OK, but it’s useless without the beautiful photos, planning and execution which would kill it’s actual completion. So, two+ projects are required 1) producing the vlog of the travel journal, and 2) doing a 4XX mile, one charge course. Both of these jobs are simple and very doable with a little planning.

More later...
I'm not looking to do this in a one-shot with my Model Y, but it would be nice to have some chargers at the various rest stops so the trip could be made without having to divert far off the trail to reach a Supercharger. Unfortunately there still aren't any L2 chargers along the way.