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I think you can do this. Realize you are probably flying out of BDL in Connecticut (Hartford-Springfield) on your way home which is IIRC less than 20 miles from Hartford. The suggestion to add a Trinity driveby is not an impossible one. Another 20 miles downriver, err.... I-91 ... would net you Wesleyan, and yet another 20 or so would get you to Yale.
While in the Smith/Holyoke area, I'd be tempted to do a driveby on UMass and Amherst, just as area information and maybe Hampshire too.
If you are doing Western Mass, I wouldn't try to do Maine unless you have a lot of extra time.
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