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By Oct 28th, the foliage will be past peak and the ag fair season over.
But the good news is that all the rural parts of CT are less than a hour from Hartford. Just stay out of the southwestern corner.
Heading east to the UConn campus is the obvoid one, a little further and it is classic New England farm country.
If you head west towards Litchfield you have the Vineyard trail, parks, lakes and rivers. It's more hilly but plenty rural. If you want to drive more than an hour you can continue out to Lime Rock Park in Lakeville. There is a bunch of fancy antique shops there and the race track. But it is a difficult place to access as there is one two lane road in and out.
South is New Haven and some overrated (yeah I said it) thin crust pizza that people consider famous along with the Yale campus.
South east coast is the Casinos and Mystic. The submarine base is also down there.
You can Google the rest but as far as day tripping goes, those are the basic compass points.
Pretty sure it's Brick oven not thin crust.