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The route of the canal was first surveyed in August 1793.
Local lore is that it is on this expedition that Baldwin was introduced to a particular apple variety that now bears his name.
The route survey, however, was sufficiently uncertain that a second survey was made in October.
Due to discrepancies in their results, Baldwin was authorized by the proprietors to travel to Philadelphia in an effort to secure the services of William Weston, a British engineering working on canal projects in Pennsylvania.
Baldwin's application to Weston was successful: Weston came to Massachusetts and spent nine days in July and August 1794 surveying and identifying two possible routes, accompanied by Baldwin and several of the latter's sons.
The proprietors then secured contracts to acquire the land for the canal, some of which was donated by its owners ; in sixteen cases the proprietors used eminent domain proceedings to take land.

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