The Connecticut River; VT vs. NH

To gloss over a bunch of history, in the middle of the 18th Century, the border between the New York and New Hampshire colonies was fixed by royal decree at the west bank of the Connecticut River. Vermont declared its independence in 1777; when they wanted to join the Union in 1791,[1] Vermont was required to accept that border with New Hampshire.

In most places, borders run down the middle of bodies of water. But not in this case. Because of where this border runs, boats in marinas on both sides of the river have New Hampshire registrations. Vermonters who routinely put their boats into the Connecticut River register their boats in New Hampshire. NH fish cops patrol the river.

Fast-forward a couple of centuries. When it comes to the construction and maintenance of bridges over the Connecticut River, New Hampshire has to pay for most of it. They have to plow and sand most of the bridges' spans. That gets expensive, especially for bridges that may benefit Vermonters more than New Hampsters.

So, a while back, New Hampshire informally broached the subject with Vermont about maybe splitting the cost of bridge maintenance 50-50. The response from Vermont could be summed up as: "Hahahaha.. no."

A similar dispute once existed between Vermont and Massachusetts about where the border ran between Colrain, MA and Halifax, VT. There was about a fifty yard stretch of State Route 112 that was maintained by nobody. It wasn't plowed in the winter and the road became heavily potholed, to the point of impassability with cars. A survey was called for, but then they fought about who would do the survey and who had to pay for it. Finally, the voters on both sides knocked some sense into the politicians, the border was fixed and the road was, too.
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[1] Yes, Vermont was independent for fourteen years. Those pissy boys in Texas? Nine years.