The High Road entrance is composed almost entirely of a highway that once cut through the center of Hopeville. It is now a ruin, complete with fallen skyscrapers and abandoned vehicles. The highway is, for the most part, contiguous, with just a few deadly gaps.
Just after the commissary terminal near the High Road Entrance, there is a large hospital cross sign laying on the road. When approaching the sign, Ulysses can be seen in the large building to the right of the Crow's Nest. He walks into the open, standing briefly in front of the partially obscured Exit sign in the building, then walks out of sight. Firing at him draws no reaction.
Upon arriving on the High Road entrance; Ulysses will speak to the courier through ED-E and depending upon the courier's responses, an additional flag may be completed for the Most Likely To...challenge:
Selecting "What makes you think this leads home?" will trigger another completion flag.
xbox360 When fast traveling to any of the locations in the High Road section of the add-on, there is a small chance that a deathclaw will spawn. The deathclaw appears on the compass as a red blip, but is nowhere visible until the player character passes a certain area. The deathclaw seems to have increased damage, as it can easily kill a level 50 player character in one hit. Going through the collapsed overpass tunnel seems to solve the problem. Four deathclaws may spawn on the High Road upon entering the it. The one that is standing on top of the trailer will charge and attack when seen, but sometimes may just fall off the road and die. [verified]
pcps3 If, upon first entering the High Road, the player manages to open their Pip-Boy menu before forcibly speaking with ED-E, once they exit their pip-boy the initial dialogue with Ulysses will never take place; ED-E will simply "say" "<happy beeping>".[verified]