Skyrim: A Craftman's Journey

Population (City, not all of the Hold)

Note that this is only people living inside the cities themselves, not counting the numerous settlements and villages that exist inside each hold.

– Solitude: 100,000

– Whiterun: 60,000 → 75,000 (after dragon hunt)

– Windhelm: 50,000 → 47,000 (after Caraxes' attack)

– Riften: 45,000

– Dawnstar: 30,000

– Markarth: 35,000

– Morthal: 12,000

– Falkreath: 15,000

– Winterhold: 7,000

Military (household guards)

This only counts the amount of Hold Guards each Hold is capable of raising. This doesn't take into account the military forces that support and exist within the holds. Ex: Empire, Stormcloaks, Vigilants, Dawnguard, College of WInterhold, etc.

– Solitude: 5,000 (Has the largest city in Skyrim and its biggest and most successful port, also the capital of the country. However, many potential guards were instead recruited to the Empire when the Civil War started)

– Whiterun: 8,000 (Lots of fertile land and the most populated with many settlements and villages, center of Skyrim's land trade, and very resource rich. Largely uninvolved with the Civil War so none were sent to support Ulfric's cause)

– Windhelm: 2,500 (low number of hold guards since most of the able bodied men and women were drafted to the Stormcloaks. Could still field a respectable amount with the dock and multitude of farmland)

– Riften: 4,000 (Plenty of fertile land and densely populated. Moderate resources and doesn't have much dangers except for the Thieves Guild (who doesn't kill))

– Dawnstar: 3,500 (Very large even though it's mostly snowy mountainous land. Has a busy port for the northern shores of Skyrim and is rich in resources with many mines)

– Markarth: 4,000 (While decently large, constant forsworn attacks has caused a major dump in population. This however causes the average men and woman to be more experienced than other holds)

– Morthal: 1,200 (A barely populated swamp with practically no settlement beyond Morthal itself)

– Falkreath: 2,000 (The center of trade between Skyrim and Cyrodiil after the fall of Helgen. Sizable fertile land and has a good number of settlements. The only thing holding it back is the low number of population to support any sizable army)

– Winterhold: 400 (While it used to be a powerful hold, its glory days are long gone. No resources to speak of, no ports, no farmland, and a city barely bigger than Riverwood. However, the protection of the College of Winterhold probably brings the power of Winterhold up a few notches.)