Can the uber-wealthy get into the U.S. undocumented via private-property helipads/airstrips?

The answer, certainly is YES practically, but NO legally.

There is probably something I am not seeing, but my thought would be to jump out over Canada and do a HAHO, er so you accidently land on the American side, could happen to anyone.

Declan

You can leave the US from anywhere, but upon return, your first landing in the US has to be at an official Airport of Entry (with on-site Customs service), or an official Landing Rights Airport (no Customs but you have to get their permission before you land there so they can come meet you), or else the jackboots will be on your neck.

But in this case, they’d probably let it go with a polite request not to do it again.

Along the Vermont border with Canada there are, or were, a number of small side roads that crossed the border. At least one of them didn’t have a customs station, just a sign that you should turn left and proceed to the customs station on another road a mile or two away. On at least one occasion we came down that road from Canada, and didn’t bother turning left. Apparently no one took any note of it.

This has probably changed in the thirty years since.

Rumour has it that a lot of the common “sneak” approaches to the USA from Canada are wired with footstep sensors etc.

As for parachuting, etc. - well, anyone can try to sneak into the USA, and might even succeed depending on planning, unexpectedness, and dumb luck. I assume border patrol in some areas of the southern border are overloaded, but I suspect the ones watching Canada and the air approaches have time to look for funny business.

However, the answer to the OP is “no”. No matter how rich, you must stop at customs one way or another, and everyone coming in better have the right papers. You mess with the border patrol at your peril. IIRC, if they don’t like what you’ve pulled and they want to be dicks, they can seize your aircraft and auction it off. Even for Bll Gates, that’s not that trivial a cost.

Post #5 mentions that a Customs exemptions can be requested and may or may not be given. Is that good information? Would Customs concievably ever “wave someone through”?

According to this is does start at Katahdin

From International Appalachian Trail - Wikipedia

I’m more inclined to believe if Bill’s personal assistant forwards (faxes?) to the customs people the names and passpot numbers of all on board, their itinerary out of the country, a list of all good purchased and what import categories they fall under, etc. and has not been a problem in the past - maybe they will simply say “OK, head to your private strip without stopping”. But if he shows up with some foreigner who needs a visa, on an impulse, they will likely be less tolerant.