Rate the cities from the most interesting to the most unimpressive.My rating is

Solitude

Whiterun

Markarth

Falkreath

Dawnstar

Riften

Windhelm

Morthal

Winterhold

My best cities are Solitude and Whiterun because they are straightforward and seem more friendly. I like Markarth also because of the dwarven ruins, despite the fact that it is a confusing city. My worst cities are Morthal and Winterhold . Both of them seem interesting when you first visit them but they end up dissapointing you because of the few quests. There is no point in visiting them, unless you have a specific quest that leads you there

Falkreath and Winterhold, two of the most disappointing things I've seen in a game.

Winterhold was once the capital of skyrim, it should've been huge. Falkreath was the kingdom of Emperor Zero otherwise known as Cuhlecain. There should've been a giant ancient colovian castle with a colovian-style town. Oh and Dawnstar was disappointing, it should've been a large walled city with a palace that dates back to the Akaviri potentates.

Windhelm was depressing, Markarth would be ok if it wasn't for the silver-bloods. I like the feel of Riften, Winterhold is pretty cool as is solitude. All of the small shack towns are disappointments.

I actually am fond of Falkreath now, thanks to my roleplay on another site.

My favorite holds are Windhelm, Whiterun, Falkreath and Dawnstar.

Whiterun
Solitude
Windhelm
Markarth
Riften
Falkreath
Dawnstar
Winterhold
Morthal

Yeah, I forgot Dawnstar. I'll add it in.

Markarth

Windhelm

Raven Rock

Solitude

Whiterun

Riften

Falkreath

Morthal

Winterhold

Dawnstar

Dawnstar, Winterhold, and Falkreath were massive let-downs. All of them should have been, well, cities - not villages. I know you have the Great Cop-Out, but that doesn't explain the others.

Windhelm
Falkreath
Riften
Winterhold
Whiterun
Morthal
Dawnstar
Markarth
Solitude

Solitude

Whiterun

Windhelm

Riften

Markarth

Dawnstar

Winterhold

Falkreath

Morthal

Whiterun

Riften

Windhelm

Solitude

Markarth

I've come to like Windhelm more than Solitude. Probably because I go there far more often than Solitude throughout my time playing Skyrim and it has felt more comfortable. The number of times I've gone through Windhelm and Eastmarch when going back and forth from Whiterun to the Rift. The western side of Skyrim is rather boring or unpleasant to be honest. I didn't go there as much as the east when I played Skyrim. I find that the villages have too little depth to bother comparing considering they don't differentiate much from one another.

I'm not sure they are all cities. I think Morthal and Dawnstar may just be towns as they don't have a temple or a barracks etc

Can a town still be a capital of a hold (county etc)? I think it can be.

They're supposed to be city. Towns in Skyrim were Laintar Dale, Pale Pass, Sungard, etc. They're just not there.

Larger Hold Capitals

Solitude

Markarth

Whiterun

Riften

Windhelm

Smaller Hold Capital

Falkreath

Morthal

Dawnstar

Winterhold

What make a town a city?

I think a capital of a hold can still be a town. Being a capital doesn't give instant city status but I think numbers of citizens and whether it has a temple, castle etc

1. Riften - if I had to live in a Skyrim city, it would be Riften. Gorgeous setting, nice enough way of life.

2. Markarth - my second home, again lovely setting and I like the Dwemer theme to it.

3. Winterhold - ok, not much by way of quests, but I like the history and melancholy surrounding it.

4. Windhelm - again, there's a certain bleakness to the place that a strange part of me enjoys...

5. Dawnstar - right in the middle, it's a nice enough place but nothing special in my opinion.

6. Solitude - close call with Dawnstar, and I have a pretty much identical view of it.

7. Whiterun - I never really saw what the fuss was about, I found it quite run of the mill.

8. Morthal - I never did forget my first playthrough when I was run out of town after getting rid of the vampire...

9. Falkreath - to be completely fair, I've never spent much time here, but on the odd visit I found it quite boring.

I like Windhelm, Whiterun and Markarth.

I like Riften and Markarth best, in different ways. Both are favourite in terms of the looks of them, Riften's got pretty houses, a nice layout and I like the colour palette. Markarth on the other hand has that "Dwemer stuff plunked down on a mountain in no real order" thing which is gorgeous, IMO, and again the colours are lovely. They also both have a corrupt underbelly, in quite different ways (particularly the stuff that goes on in Markarth which isn't actually corrupt in the governmental sense, but in a different one). I prefer the people of Riften, though, on the whole (so long as I stay out of earshot of Maven and her croneys.)

I like Morthal, but it's pretty bleak and definitely not as city-ish as it should be. Windhelm is okay but also quite depressing and Blood on the Ice irritates me so much that I end up avoiding the place. Solitude's nice looking but there's little going on there that interests me all that much. I have a soft spot for Whiterun, and it's a decent enough place, good shops and so on, but it's kind of boring, no? And Dawnstar's a bit meh, and Winterhold's a depressing dump. Oh, and Falkreath is meh as well, plus I feel guilty every time I see the blacksmith and haven't brought him that dog yet. Maybe I could bring him Meeko... (That would actually be quite nice, to be honest, wonder if anyone's bothered to make a mod for it...)

Riverwood. No guards.

Bigger population, sustainable economy, a palace, etc...

Dawnstar and Falkreath were supposed to be massive cities guarded by ancient fortresses (Akaviri and Colovian, respectively).

Whiterun

Solitude

Riften

Windhelm

Markarth

Windhelm, Whiterun and Riften are my favourite cities, mostly due to their surroundings. And I actually like Falkreath... it just seems so serene. Although there is the reminder that the town is literally just a graveyard at every corner.

1. Riften

2. Solitude

3. Morthal

... then the others.

Large cities

Riften

Whiterun

Solitude

Windhelm

Markarth

Other cities

Falkreath

Riverwood

Morthal

Dawnstar

Winterhold

Personally, I can't stand either Windhelm nor Markarth, although Windhelm wouldn't be quite so bad if it weren't so closely tied to the dirtbag of Skyrim. Interesting town, but a piss poor Jarl running the show.

You're right, they are towns. They're just not supposed to be, not according to what they taught us Skyrim was before the game was shipped. The actual towns that were supposed to be dotted around mostly got removed, and they made the hold capitals smaller. Winterhold especially was a massive disappointment, and so much could have been made of Dawnstar. The ice-tribes, islands in the high Arctic, the Akaviri fort and all that. I don't know what they did instead with the time, but I sure hope it was worth it.

I'm not going to put these in any particular order but here's my feelings on the cities.

Winterhold is very lackluster although it does give an isolated feel which could be cool for some characters. If it didn't have the college it would be completely useless.

Falkreath is a very average small town, I would say it's very bland. It does have an alchemy store which not a lot of small towns can say that. The hold is fantastic.

Morthal is probably the worst town/city in Skyrim IMO. There's nothing that excites me in that town. It too is very bland but unlike Falkreath the hold doesn't offer much.

Dawnstar is a decent small town, I actually like it the best out of the 4 smaller cities.

Whiterun is a great town, that's very centralized and it has the companions guild. I personally love this city.

Windhelm is probably the worst big city, the snow makes it feel cold but the town doesn't really offer much.

Riften is a nice city, it has the thieves guild although it's corrupt. The hold though is fantastic.

Markarth is underrated in my opinion. The Dwarven building style gives it a unique look and it has one of the best holds in the game from both gameplay and asethics.

Solitude is probably my favorite city in Skyrim, although the hold is kind of lackluster. It does have some of the better side quests in the game.