I haven't been to them all, but of those I have it's hard to say anything but Whiterun.

First experience here is a racist bullying scene...first experience there is a public execution...before I even get to there I conclude the Jarl is in the pocket of some scummy robber baron...I walk in the gate of this other place and some thug wants to run me off before I even get ten feet from the shakedown artist guard that let me in the gate...

Okay, so I no sooner got to Whiterun than I got roasted by a dragon, but still...

Didn't expect Whiterun to have so much backing. Am I the only one who finds Whiterun rather dull and empty compared to the other Holds/Cities?

I HATE Whiterun's NPCs and find it's capital rather bland.

Really, you would have thought the "Gateway to Cyrodiil" and the most historical gravesite in Skyrim would have merited a bit more then three quests on the questing front.

That being said, the place is THICK with ruins and caverns and the like, making it good hunting. The fact Lakeview is nearby is also nice.

*Raises hand*

It's so...generically boring. It's the Balmora of Skyrim. I don't tend to linger there any longer then I have to.

I kind of like Whiterun too. Friendly city, nice scenery, and flat enough that it's harder to get lost there.

Not fond of Eastmarch. Had I been running the Civil War, I'd have taken the rest of Skyrim and let Oafric have Eastmarch all to himself. Maybe Winterhold too, since it's essentially an enormous ice cube.

I think people like Whiterun for the same reason they liked Balmora. First major city, relatively friendly, and a central location. Meanwhile I was always chilling in Sadrith Mora or Ald'Ruhn.

Probably.

I love Whiterun (its a small reason of why I normally side with the Empire, but lets leave that fir another decade).

Personally, I find many if the other cities dull ajd empty.

I was an Ald'Ruhn guy myself.

First major city, relatively friendly, central location...definitely all good qualities.

In Morrowind I liked the Redorans. I could role-play as a scummy Hlaalu or arrogant Telvanni, but I generally liked the Redorans. I can't say that I so much like the people in Whiterun, but the others so far have been really distasteful. My current play is a main quest straight liner to get a feel for the game and the world, but I can already see a couple cities where I could easily do a 'slaughter all or at least most of the populace' play through and feel good about doing it. My son just started a 'kill everyone in Markarth' game and instead of thinking 'that's an appalling objective' my first response was 'good idea'.

Well, Whiterun was the first city I ended up in so it will always have that "homefeeling" to me.

As for actual favorite, the Rift.
I love that mystical-autumn-forest-atmosphere.
Besides, Riften have, more or less, all I really need in a city (except a smelter >.<)