Interesting thread.

I'll second the recommendations re Portland, Oregon and Portland, Maine.

New Orleans, definitely.

Also, Baltimore, especially but not only if you like crab.

Charlottesville, Virginia.

I recently visited Pittsburgh briefly a couple of times, partly to visit my niece who'd started college there. I didn't see enough of the town to give a really knowledgeable recommendation, but its rivers and hillside provide a much prettier setting than I'd expected.