It's probably safe to say that no other place in video games has been more frequented and visited than Skyrim. The game has been going strong for nine years now and it will likely remain popular come its 10th year in existence as a complete game. Skyrim will always be a home for many players who have gone in other open-worlds as it's one of the most recognizable.
Of course, when taking a virtual vacation in the land of the Nords, it doesn't hurt to plan out an itinerary. After all, Skyrim's holds and provinces are not made equally and some are worth more of your time than others. So don't just jump into a new game without some newfound appreciation for the cities and large towns of Skyrim. Climb in the back of our cart and we'll be off to the crown-jewels of this war-torn Tamriel province.
Updated November 16, 2021, by Sid Natividad: With the release of Elder Scrolls 5: Skyrim Anniversary Edition, we all get a new and upgraded vacation stay in Tamriel's coldest province once again. As always, Skyrim's roads and wilderness are fraught with loud bandits, pesky dragons, and terrifying mudcrabs. It's best to stay in the cities, to be honest.
Thankfully, there are many things to do in each of Skyrim's major holds and settlements. Apart from the usual sightseeing and real-estate shopping, you can also attend to the main story or quest offering of said city. Hence, we've listed down what makes each city special or notable as far as questlines go. So that maybe you attend to them first before lollygagging.
10 Winterhold
We're not even sure why this one continues to be called a "hold." It's clearly less than a hamlet by the current timeline of the game and the only notable structure is that weird mage college from afar that has a questionable curriculum.
Winterhold, for that matter, is by far the most destitute hold in Skyrim after a supposed accident with tsunamis swallowed a huge chunk of the town. Now it's barely recognizable and much less so with its frigid position way up north.
Notable Feature: College of Winterhold Questline
For any other class in Skyrim, Winterhold is just a decrepit fridge but for mages or some kind of hybrid spellcaster, it's a gold mine of experience and items.
It houses the College of Winterhold which contains the most in-depth spellcaster questline in the game. If you finish it, you get to be the school principal along with some nice robes.
9 Falkreath
Falkreath is a small and lovely respite from stonewalled civilizations and much like Winterhold, not much is going on in the local area. However, Falkreath is still more desirable than that desolate fridge because of its warmer climate and dreamier haze.
It's surrounded by a forest too, making it a good outpost from all your mountaineering and camping. It wasn't always a part of Skyrim, however, as Falkreath has changed hands many times between the Imperials and the Nords. That sort of explains why it has one of the biggest graveyards in Skyrim.
Notable Feature: A Daedra's Best Friend Quest
Falkreath is relatively less eventful compared to the other Skyrim holds but it's full of odd quests that deal with spirits and of course, Daedric Princes.
Clavicus Vile is one of those princes and he has quite a surreal presence in Falkreath via a talking dog who's dealing with employment problems. It's definitely a quest to remember.
8 Morthal
Looking for a place that's seemingly insulated from all the Jarl politicking and the Tamrielic province woes? Morthal is one such area and its residents love to distance and isolate themselves from all the disturbances and turmoil inherent in their home province.
It does help that Morthal is surrounded by a marsh, making it less accessible and strategically important compared to other holds. Sadly, this fixation for keeping the local peace and quiet has led to the residents of Morthal being unwelcoming towards newcomers.
Notable Feature: Laid to Rest Quest
Laid to Rest is a classic investigation quest about a burned house and possibly murder and infidelity. You're tasked with finding out the truth behind why Hroggar's house burned down with his wife and child inside it and why the man already has a new lover shortly after the disaster.
7 Raven Rock
It's not located on the mainland as Raven Rock rests at the harbor of Solstheim which is an island between Vvardenfell and Skyrim but nevertheless, it's an important part of the game. Raven Rock is one of the busiest dock cities or towns in the region.
It's home to a bustling population of miners, merchants, and treasure hunters looking to make a profit in the turbulent winds, snow, and sands of Solstheim. Raven Rock is busy and pretty enough especially for those looking for a change of scenery from all the Norse and Viking iconography.
Notable Feature: Earth Stone Nearby
The Earth Stone isn't exactly in Raven Rock's immediate vicinity but it's a short walk away. You'll immediately spot the weird ritual site full of uncanny individuals and if you talk to them, they don't actually know why they're there or what they're doing. It's one of the eeriest ways to set up the happenings in Solstheim.
6 Dawnstar
Dawnstar had a pretty big contribution to the guilds of Skyrim as they popped up like mushrooms after martial law was declared in the province following the destruction of a fortress in the city. With that said, Dawnstar has seen better days.
It doesn't look as fortified as before and its current citizens are suffering from nightmares due to a certain Daedric Prince. In any case, Dawnstar is an important city and holds the key to many rich mines and trading resources, making them a high-activity area. The dragons seem to know that as well.
Notable Feature: Pieces of the Past Quest
Dawnstar is also another calm and quiet place in Skyrim but it does have some tension-filled quests. The most notorious one and also arguably the most rewarding would be Pieces of the Past.
This is the quest where a Mythic Dawn supporter opens up a museum dedicated to the infamous cult who assassinated Uriel Septim VII and served as the villains in The Elder Scrolls IV: Oblivion. They also worship Mehrunes Dagon and the quest will grant the players his legendary dagger.
5 Riften
It might be one of the biggest cities in Skyrim but it's hard to recommend this wretched place for a little R&R. You don't even have to enter the place to experience how bad the corruption in Riften is, simply walking by the gate is enough to get swindled by the guards.
Once you get in, the whole place just reeks of crime and thuggery. Soon enough, you'll realize that the very foundations of the city itself are dishonest work and dirty money. But hey, if that excites you, then head on over to the sewers for some cloak and dagger betrayal.
Notable Feature: Thieves Guild Questline
Upon entering Riften for the first time, the local guards will try to swindle you. That sets the tone for what kind of deceitful hive of scum Riften is in Skyrim.
Near the top of the food chain, of course, is the elusive and mythical Thieves Guild. You don't exactly have to break a sweat trying to get in, Brynjolf will scout you. They're low on members, you see.
4 Windhelm
Windhelm is a disputed capital of Skyrim because in the current timeline, it houses Ulfric Stormcloak and his army. It's a walled city that also boasts a dock that can connect to Vvardenfell and Solstheim, making its location strategic in Tamriel.
When it comes to size, Windhelm is quite a beast of a stronghold and all the homes and structures are made mostly out of stone to keep out the howling winter winds of Northern Skyrim. Sadly, it's neither the biggest nor most impressive out of all the holds.
Notable Feature: Jarl Ulfric's Throne
Windhelm is Ulfric Stormcloak's seat of power and given his philosophies and attitude, the whole place is a reflection of extreme Nord culture. That means nearly everyone in his throne room is xenophobic, heavily muscled, and sleeps while hugging their axe. Don't feel bad for trying to take all the food and utensils on Ulfric's dining table.
3 Markarth
Markarth is probably considered as one of the most novel cities in Skyrim since it was built by the Dwemer or the Elder Scrolls' fancy word for dwarfs. As such, Markarth is a city carved out of a mountain, making it a fan-favorite especially with the added allure of the lengthy city questline.
The city is also a big place with impressive waterworks and structures and roads chipped away from the mountain stone. As for the attractions, walk around a bit in Markarth and there's bound to be no shortage of things to do, even the surrounding area is a busy place.
Notable Feature: The Forsworn Conspiracy Questline
There are lots of notable quests in Markarth but none of them will grab your attention immediately and violently as The Forsworn Coinspiracy.
It happens abruptly upon entering Markarth for the first time. A murder happens right before your very eyes and you get to pick up a note from the murdered which will then lead you in quite a maelstrom of adventures including a delicate prison break mission.
2 Whiterun
The most popular city in Skyrim, is the very first one players get to visit and witness in its wooden splendor. Whiterun is a bold city that placed itself in the middle of an open plain but it has proven that it can withstand any attack from any angle.
It's also one of the most relaxing cityscapes in Skyrim ever since it has a dedicated park and large open space for loitering around and/or lollygagging (just don't let the guards catch you). What gives it the feeling of home though, is its residential composition even if half of them are social climbers and warmongers.
Notable Feature: The Cloud District
Do you get to the Cloud District often? Oh, what am I saying, of course you do! It's only the Dragonsreach area in Whiterun, nothing special, mmkay, Nazeem?
In any case, lots of beautiful and epic things happen in Dragonsreach. The most important of which is catching a dragon and regularly seeking Jarl Balgruuf's audience. Don't forget to shout his sassy son Unrelenting Force.
1 Solitude
As for the most unique conventional city in Skyrim, Solitude can be hard to beat. It's a city built on a natural mountain bridge, making it one of (if not) the prettiest. Solitude's area extends beyond its games though and it also has a dedicated dock that connects to the major seas and rivers of Tamriel.
Outside the gates are also respectable pockets of farmlands and peasant cottages. Meanwhile, the inside of the walls has enough space for a full garrison of Imperials to show just how much of a sellout Jarl Elisif is to the Empire. Still, if you ever wanted a retirement house in Skyrim, Solitude is the premium location.
Notable Feature: The Mind of Madness Quest
Between this quest and the Bards College questline, it's a tough call. While the latter gives players good chunks of skill points via training and fetch quests, you can't beat meeting good old Sheogorath face-to-face and at a party. He's the Daedric Prince of madness and an Oblivion expansion was dedicated to him, meaning he's entertaining enough to provide limitless content.