Outskirts vacation
From Halopedia, the Halo wiki
The Rooftops Vacation, or simply, the rooftops, is a small programming oversight, similiar to The Delta Halo Vacation, The Metropolitan Vacation, and The Cairo Station Vacation. it allows you to reach areas of a level previously thought to be inaccessible. This is found on the level Outskirts.
How to reach it
Play the level as you would normally. In the courtyard, kill the Hunters when they come out of the large metal door. Enter the door, but dont continue. Turn left, and you should see two black wall type things sticking out of the wall. Jump on to the top, or better, crouch jump onto the first one. Then continue onto the second one and stop. There should be a pinkish building ahead of you with a small wooden awning over a window. Crouch jump onto the awning, and once on it, turn 180 and you should see a long black awning. Jump onto here but stay away from the edges. Keep walking down and you should see a broken rootop. Hop on to it (Phase one complete) Continue along until you're on the other side. Then there should be another long black awning with a light on over most of it. Jump to the uncovered part, which is in the front, then crouch down and crawl under the light. You should be on the other side. Turn right and there will be a small rooftop with a clothesline over it. Hop in. Hop onto the wooden awning above the door, and congrats! You've made it to the roof top. Explore around! If you go onto the top of the broken highway and keep going to the end, youll be off the end of the map xD!
Alternatively: Right at the beginning of the level, before you kill the first grunt and right after leaving the crashed Pelican site, jump onto the light fixture across from the door, turn left and crouch-jump onto the roof, as if you were going to the Blind skull, except turn around and jump across the gap away from the skull and with the crash site now on your right. Grenade jump onto the ledge to your right and now you can explore all the rooftops in the city. Alternatively-alternatively, go up to the roof as if to get the Blind Skull, but instead of turning left into the hallway, go straight ahead to the ledge, stand on your partner's head, throw a plasma grenade on him, and time your jump so that you land on the roof. Note: this method requires co-op and takes a lot of practice getting yourself to stay on your partner's head without drifting.
Different Vacation in the second part of Outskirts
There is another vacation in outskirts that was found recently. Here is how to do it: After going through the Hotel Zanzibar, get in the warthog and drive to the smashed Tunnel. I recommend destroying the Phantom's turrets to make it easier to get on top of the tunnel. Now, see where the Phantom hovers and drive the warthog against the small ledge closest to the opening. Jump onto the warthog and onto the ledge. Now face into the tunnel, towards where the ghosts are parked, and you should see a small ledge small enough for you to jump onto the roof of the tunnel with. Have Fun!.
Easy Way To Get On Rooftops
My friend and I found out a really way to get outside of the map onto the rooftops on cooperative. You never have to fight any enemies. When the level first begins, have your friend turn around and jump ontop of the pelican. You must then jump on top of your friend's head. You may have noticed several broken steel beams that protrude from the concrete roofs. The way to get out is simply to crouch jump off of your friends head onto the beam above the pelican and walk onto the rooftop. You may have your friend commit suicide so that he or she will spawn next to you on the rooftops once you are up there. You now have free reign over the map. Note: This has only been tested on heroic.
"Super easy way to rooftops and energy sword"
Once the hunters break down the door, use the turret to kill them. Then run through the door and kill all of the jacks. Jump on the green boxes and then onto the raised concrete section. Jump onto the gray bin and crouch jump onto the lightpole. Turn left and jump onto the biege/orange colored building. Turn right and go onto the steel bridge and turn right onto the broken freeway. Go to the edge near the rooftops and jump onto the little ledge. Look up a little bit and crouch jump forward onto the roof. From there, turn right and walk down to the end and jump ont the other rooftop. Go forward until you pass the tall tower and jump down to the lower part of the building. Go straight and jump onto the heaters(make sure you are on the 2nd row of them). From there jump on top of the small room in front of you and go through the shatered roof. There is an energy sword lying on the floor of the room.
The easiest way to skip half of the level outskirts In the beginning, do what you normally do and get outside. Go to the huge metal gate. Turn left and go forward until you come to a small slanted walkway on your right. You should see it after a couple seconds of walking. Walk in and then turn right and you should see a small pile of rubble on your left that is up against a wall. Walk on it and crouch jump up. The go forward again and crouch jump up again onto the roof that is right in front of you. Turn 180 degrees and jump onto that roof. Keep going forward until you reach a weird looking thing with thin beams. Run up that and turn left, keep jumping until you get to the part where there is the broken bridge thing. There is a building ledge right before the bridge, jump on that and jump on the bridge, wait til the Pelican comes, and when it lands jump crouch on it and go near the front of the Pelican and stand on the right engine/wing thingy. When it starts to go up, jump crouch onto the roof/ledge you see on your right . From there you keep jumping around until you reach the part with the jackal snipers and no one is there, from keep going untill the part where u meet up with ur guys and thats where the vacation ends.
The VERY easiest way to skip half of the level outskirts From the start,leave the pelican.Then wait near the door.meelee the grunt that walks by to death then look at the door infront of you. Crouch or grenade jump on the metal bar ontop of it,then look to the left.You should see a ledge.Crouch jump onto it.to the left you will find the blind skull. Look to the right now.you'll see a "hallway". Move through it and grenade jump to the top.Then you can move freely through the level and this can also be used to trigger the i would of been your daddy skull.
--74.101.130.62 11:00, 24 February 2007 (UTC)last paragraph by Arc9