the-elder-scrolls-v-skyrim
In the Jarl's quarters in Dragonreach (in Whiterun) is a map on a table with red and blue flags marking areas held by the Imperials and Stormcloaks.
I'm still early in the game, so is this map used for some purpose other than the ability to add those locations to your map, perhaps after choosing a side? Currently, clicking on a flag will add the location to your world map.
What we've got definitely isn't comprehensive, and portions may be too specific:
= Settlement
= House
= Wheat mill
= Lumber Mill
= Farm
= Stable
= Port
= Mine
= Shack
= Lighthouse
= Imperial Army Camp
= Stormcloak Camp
= Nord Tower
= Imperial Tower
= Fort
= Dragon + Word Wall
= Standing stone
= Barrow/Tomb
= Surface Encounter
= Giant Camp
= Cave
= Daedric Shrine
= Dwemer Ruins
= Camp
= Orc Stronghold
= Ship
= Pond/Clearing
= Grove
= Mountain Pass
= Generic point of interest. (Guild halls, some quest encounters, ect...)
= Quest Marker - The quest is in the same zone as you.
= Quest Marker w/ door - you must pass a loading screen to get to this destination.
In addition, each city have a unique emblem, as do each palace.
(Images from the UESP)
Well, if you can figure out where they're pointing, they'll lead you to a chest!
See this from Reddit.
I'd link directly to the image, but it's huge. Bottom line, there are at least 10 of these, each of which leads to a randomly generated chest of loot. (The location isn't random. The contents are.)
Best Answer
There are a bunch of these maps around Skyrim. They're basically marking the current territories of the Stormcloaks vs. the Imperial Legion. As you progress in the civil war questline, these flags will change color as regions are captured.
They're basically are a visual representation of who's "winning" the civil war.