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Street parking / charging - is the 220V adapter a good choice?

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I think that generally you do own the property all the way to the curb. The sidewalk being a public right of way usually maintained by the city/county, but not always. I agree that liability is the bigger issue. In any case, curbside installs are not unheard of, and there's probably some permit hoops to jump through to do it correctly. I would not do the mobile connector unless I were to put the whole thing in a weatherproof housing.

One other issue is that usually street parking is not reserved, and somebody could block you out. It may be possible to designate the parking as EV charging, but that would be another hoop to jump through.

These things vary, but in most cities the right of way extends to the home side of the sidewalk. Whether the city owns it or simply has an easement makes little difference. Get permission and permits for the work. My 25 years as a municipal attorney (and instructor) urges caution. Many cities are EV friendly.
 
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It might seem like I'm joking, but being the one to go to your city-council mayor/members (or city government) is actually the thing to do here.

You get permission to drill a hole in the sidewalk and/or make yourself a driveway and you're fine.
 
What about if a cable ramp was used across the sidewalk? Something like this (the first one I found, but they are readily available)
This is exactly what I was thinking of doing in my rowhouse here in DC - I telework so can usually get the spot right in front - there is a 110 outlet out front but I'd want to get a 220 so I dont have to leave it plugged in for too long. Just FYI however I did email the DC Dept of Public Works and he said its absolutely illegal to string anything across the sidewalk, even w the cord cover.. I see them all over the place for construction work, etc tho - pretty disappointed as I have no dedicated parking in the city.
 
I have a friend who has a model 3 and parks on the street. She installed a Tesla wall connector on the spiffy aluminum post they sell, and runs the cord across the sidewalk (under a cord guard thing so people don't trip) when she wants to charge. Her neighbors are nice and don't park in front of her house, and she says she only charges about once a week.

I am pretty sure she didn't get permission for this, come to think of it, but it doesn't seem to be a big deal. Helps to live in a smallish southern city I guess. And I agree that most municipalities (including my friend's) would probably take a dim view of running a cord above the sidewalk, even with a cord guard.

I would only do this with the wall connector since it's outdoor-rated and weatherproof. I don't think the mobile charger cord that comes with the car is weather/waterproof.