Wow, thank you for sharing this! I have also been interested in and learning about how the early settlers planted in my area, and part of how we grow our Victory Garden(s?) will be based on how they did it. We're new to New England, and I figure the best place to learn is from the original teachers - the pioneers who learned by doing it, right here!
Allyson...I'd love to read what you discover about your region!
So far, not TOO much, but I've only just started. 
I know that people here used to grow something called "mangles" which are somewhat like a turnip. They can be eaten by humans, but generally were grown as a high vitamin livestock feed. We plan on importing some from Europe (they aren't grown here anymore, but not for any ecological reason we can find) to feed our (prospective) Highland cows and goats.
People around this area farmed the Connecticut River valley, which is where our new farm is located (our kitchen looks out onto the river itself!), because of the rich soil. We plan on growing a variety of vegetables: rattlesnake green beans, bush beans, tomatoes (of course), zucchini, winter squash of many varieties (including Hubbard, which is MASSIVE), pole beans, snap and Lincoln peas, spinach, lettuce mixes, beets, cabbage, carrots, onions, and garlic. I'm sure there's more, but that's what we usually grow, anyhow. Our expectation is that the highly fertile soil will make things much better here than they were in the dead rocky soil of PA.
Come spring, we'll be planting saplings: semi-dwarf versions of apple, pear, plum, cherry trees, and mullberries, raspberries, blueberries, and anything else we figure we can get to grow here. We will be walking out our orchard space as soon as the farmer cuts the corn in the field that is now ours.
In the future, we'd like to have wheat, oats, and barley growing, likely both spring and winter versions. We'd like to attempt to be as self-sufficient as we can, without walking away from modern life. We'll keep our internet, our HD television and movies, and occasional steak dinners out of season. 
But our general daily life we plan to be as close to seasonally correct as we can. If life treats us well, we might have our own grain next fall, and I will be baking bread that comes almost entirely from our own supplies.
OOOH, This gal speaks my language. Years ago I took my kids to visit an old farmstead museum near Dallas, that the city of Plano had grown up around. I was just mesmerized by the simple frugality and common sense of it all - the cistern, the root cellar, the garden shed full of windows and light for the potting benches, the vegetable and flower gardens, etc., that it's been part of my vision of a reasonable life ever since.
Allyson - Thanks for the scoop! I'd love to visit New England. Only been to NYC, alas...
Becky - Isn't Susan great?
Well, we have a "portable garage" we plan to turn into a greenhouse for in the spring, and I'm hoping to get some cold frames built before the heavy frost hits, so they can be used in the spring. I'm new to some of this, though. I've always had gardens, but never on this scale, so it's new and exciting at the same time as being just a bit scary.
Great blog! Are you open to selling ad space in here? I would love to buy a link for my gardening shop from your blog.
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