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Medford to Dedham will be very rough, especially with the route you want. I-93 through Boston is extremely packed in either direction, both times of day (really, even off peak times).
From Newton, depending on where you are, you could take Dedham St./VFW Parkway southward to get to Dedham. It's only a 7-9 mile trip that way. Sure, there are lights, but you won't have to try to navigate I-95, which can be sometimes unpredictable.
I would highly suggest Newton. It's really one of the best places in metro Boston.
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