List: Prominent cities and their respective months by the rule of esotericnessness.
Toronto - January (Twin Cities if we sticking to the US) - If you want to celebrate the cold, the best places to be in.
Chicago - February, Chicago has an "we here, what can we do about it" energy, plus it's brutally cold winters strike fear into the hearts of its residents.
New York - March: March Madness.
San Francisco - April - look at the weather.
Los Angeles - May - again, look at the weather.
Miami - June - again, look at the weather.
Atlanta - July. Hotlanta. I visited Clark Atlanta and Morehouse one summer. Saw a wall of humidity and 800 foot tall trees.
Houston - August
Dry heat to burn your feet.
Washington DC - September
It's nice, and important like September
Seattle - October - Seattle and the Pacific Northwest all feel like Winter is around the corner.
Philadelphia - November - Philly is very homely and fulfilling. Even the word has "phill" in it.
Boston - December - Cosy