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The Elder Scrolls V: Skyrim Hints
How can I get to Castle Dour?
1 of 6: Go down the street to the open-air marketplace to encounter several Imperials. Hang back if necessary to let Ulfric and his men take them down.
2 of 6: As soon as you can, bash (or burn) the two wooden barricades that are blocking the huge archway near the open-air market.
3 of 6: Wait near there until Ulfric and the rest catch up, then move down the street to a split.
4 of 6: Turn left and wait until Ulfric's men engage the enemy, then sprint past them and turn left again to find another wooden-barricade-blocked archway.
5 of 6: As before, destroy both barricades and wait for your allies to catch up before going through the archway.
6 of 6: Help finish off the enemy soldiers in the courtyard, then go enter the castle. (Or run over and enter the castle before all the courtyard enemies are killed.)