Merle had been born and raised in northwest Connecticut, a region of clockmakers, gunsmiths, and inspired thinkers, so his trip out to the Western Reserve was just a personal expression of Yankee migration generally.
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"northwest Connecticut"
The county of Litchfield, or possibly Hartford. Having grown up as a Bay Area resident in California, I know that looking at a map and describing the area of the state I grew up in as "Northern California" can seem to be at odds, so I won't judge if the people of Connecticut want to call Hartford County "northwest Connecticut."
"a region of clockmakers, gunsmiths, and inspired thinkers"
Seeing as how gunsmith is included here and assuming Pynchon means Samuel Colt who was from Hartford, it strengthens the argument for northwest Connecticut being Hartford County. Not to mention how every mention of Merle in Connecticut has been in relation to Hartford and Yale. Oliver Winchester was also from Connecticut but New Haven County rather than Hartford and New Haven is decidedly southern Connecticut.
Eli Terry is probably the clockmaker, also from Hartford County although he later moved to Northbury (later Plymouth) in Litchfield County so maybe I'll just believe northwest Connecticut applies to both counties. Apparently his work ignited the industrial revolution so that's probably important.
I don't know who the inspired thinkers might be there are too many people who could fall under that category. J.P. Morgan is from Hartford so we'll just go with him as the best example since he'll probably be important later.
"Western Reserve"
The original charter for Connecticut from 1662 marked its western border as the "South Sea" (Pacific Ocean). So Connecticut was a long-ass state. Almost immediately there were conflicts with New York which were ultimately resolved so that the long stretch of land to the Pacific was cut off from the rest of Connecticut by New York's dangly bit. The portion of Connecticut west of New York was called the Western Reserve. Unluckily, Pennsylvania also had claims to this land via the Dutch and also because it was sold to them by the Iroquois which seems like a reasonable trick to play on the European invaders.
"personal expression of Yankee migration generally"
Merle is headed toward Cleveland, Ohio, which would have one time been a part of Connecticut according to the original charter and the Western Reserve. So Merle's trip can be seen as merely an example of another Connecticut Yankee heading out to settle Connecticut's western frontier. He refers to himself as "Yankee" to remind the reader of the Pennamite-Yankee War fought between the people of Pennsylvania and the people of Connecticut over this chunk of land. I use the verb "remind" so it seems like I once knew about this interstate war but had forgotten about it. And maybe that's true and I didn't just learn about it this late in life because how am I supposed to remember what I have forgotten?
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