The Webster-Ashburton Treaty gave all of northern Maine to the Americans. If this had not been the case, the Maritimes would not have been nearly as geographically isolated from central Canada. It's interesting to speculate how this might have changed the economy of the Maritimes in general (and NB in particular).
Alternatively, a little known chapter of the Revolutionary War is the
Eddy Rebellion. Jonathan Eddy was a planter with revolutionary sympathies who obtained a letter of support from George Washington to try and sway Nova Scotia to the separatist cause. In 1776, he and a group of sympathizers launched an attack on Fort Cumberland (formerly Fort Beausejour) near Sackville NB. They very nearly took the fort, which would have allowed them to control land access to peninsular NS, and have given them a base of operations to continue to harry British forces in the Maritimes. If they had ultimately been successful, NS (and NB) might now belong to the USA.
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