Favorite city is Solitude because its heart of Empire in Skyrim, second favorite Markath because its amazingly beautiful.Third favorite is Winterhold - i like snowy mountains,college,beatuiful outlandish landscapes and tons of snow.
Least favorite is Windhelm because Windhelm full of racism and racistic npcs and only few Windhelm npcs is fighting racism. Also i dont like Windhelm landscapes
A POX ON THE EMPIRE! the emperor can kiss my as#s

favorite city is solitude because it's the most medieval looking city (better yet after a Stormcloak siege

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my favorite city would be Winterhold if they didn't had blowed it up, soo many wasted potential, loved Winterhold from TES Arena

least favorite is Markarth, notthing against the city itself, just don't like the Dwemer architeture, and that city is all about it qq-