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Hard to say, but if you include places where I have driven through and did not stop as having never been it would have to be Chesapeake, Virginia. Stopped over in Norfolk, Virginia Beach, and Portsmouth, but there is really no reason to go to Chesapeake unless you live, visiting family/friends, or work there. If you include places I have driven through as having been there than I believe Leesburg (Virginia's largest incorporated town) is the largest place I have not visited. Poquoson, VA is the largest incorporated "city" I have not driven through or stopped in.
I dont recall ever going to California's 15th largest city, Chula Vista(Pop 275,487)
I've been there lots of times (have friends there), but haven't been to #3, San Jose. Unless you count the airport, which I don't.
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