What do the different symbols on the map represent?

What we've got definitely isn't comprehensive, and portions may be too specific:

  • big house = Settlement

  • small house = House

  • Mill = Wheat mill

  • Water Wheel = Lumber Mill

  • sickle = Farm

  • horseshoe = Stable

  • anchor = Port

  • mine = Mine

  • shack = Shack

  • lighthouse = Lighthouse

  • imperial = Imperial Army Camp

  • paw = Stormcloak Camp

  • Nord Tower = Nord Tower

  • Tower = Imperial Tower

  • fort = Fort

  • dragon = Dragon + Word Wall

  • stone = Standing stone

  • barrow = Barrow/Tomb

  • helmet = Surface Encounter

  • Tusks = Giant Camp

  • cave = Cave

  • shrine = Daedric Shrine

  • dwarf = Dwemer Ruins

  • tent = Camp

  • orc = Orc Stronghold

  • ship = Ship

  • treehill = Pond/Clearing

  • pine = Grove

  • pass = Mountain Pass

  • shield = Generic point of interest. (Guild halls, some quest encounters, ect...)

  • Quest Marker = Quest Marker - The quest is in the same zone as you.

  • Quest Marker w/ door = 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)