From the bank, head a little west on Brite St.  The next street after Lansdale Ave is Laymond Ave. Turn north on Laymond Ave. There are two underground entrances in the area. One leads to a dead end, but in the other one you squeeze through a gap between some barrels and a wall. Find a homeless man trying to keep warm using a fire he has lit in some can. He tells you how dangerous the rain can be. But he can show you another way to get around town if you can spare something to eat.

The rest of the quest will consist of you fetching items for this homeless man. The location of the items will be different depending on your puzzle lvl difficulty setting. We have compiled maps of where the items are. Be sure to bookmark this guide so that you can return to it at any moment.

Downpour Homeless Quest

1: Location of Homeless Man - Quest Start
2: Vending Machine (Easy)
3: Vending Machine (Normal)
4: Vending Machine (Hard)
5: Thrift Shop

Downpour Homeless Man Side Quest

6: Fishing Rod (Easy)
7: Fishing Rod (Normal)
8: Fishing Rod (Hard)

You need to find him some food. If you have the candy bar in your inventory, give it to him now. Otherwise, exit the subway and head south. The location of the vending machine for the candybar will depend on the level of puzzle difficulty you have set. The harder your puzzle setting, the further you will have to go to located the candy bar.

Easy: Go south on Laymond Avenue until you hit Brite St. Look for the vending machine next to a building on the south side of the street

Normal: Go to the intersection of Cook and Lansdale and look for a vending machine near a building in that area

Hard: Go down on Laymond Ave until you hit Cook, then go around and enter an alley. Find the vending machine there.

Once you have located the vending machine, open your inventory and use money or change on it. You will receive:

Candy Bar
A "Granny Pat's" 100% organic milk chocolate bar.

If you do not have money, try looking in the cash registers in the movie theater in Chastain Heights.

Go back to the underground entrance and give the candy bar to the homeless man. He asks you if you have a map of town and offers to show you something. He tells you there are tunnels all over Silent Hill, connecting one part of the town to the other. The diagram he shows you in your journal includes Hillside, Pearl Creek, Chastain Heights, Pleasant River, and the Port District. He tells you that if you use the tunnels, think like a rat, you can stay out of the rain and have more chance to survive.

He tells you that it is cold, and that if you found him a coat to keep him warm, he could show you some more shortcuts to keep you dry.

Go west on Brite St, as it curves to the north. There is a thrift shop on the west side of the street, across the movie theater. Enter the shop. The location of the coat will be different based on puzzle difficulty:

Easy: You will see the coat as soon as you come in, it is right across you, on a mannequin close to the cash register

Normal: Open a door to enter the storage room. The coat will be hanging near some shelves in the corner

Hard: The coat is all the way in the back of the storage room.

You get:

Old Coat
A warm looking coat

Take the Old Coat and go back to the homeless man in the Pearl Creek underground entrance.

He thanks you for the coat and adds some more shortcuts to your map. Next, he tells you that instead of living like some scavenger, he could fend for himself. The lake out there is full of fish. If he had a rod and reel, he could feed himself. He offers to show you yet another shortcut if you bring him a fishing rod.

The fishing rod is in Pleasant River. From the intersection of Rice and King St, go left towards the docks. The fishing rod will be in a different location based on puzzle level:

Easy: Fishing Rod is towards the center of the docks, close to the water

Normal: Fishing Pole is in the south part of the docks, close to the Pleasant River underground entrance, near where the ladder to go down is, by the spillway. (climb down the ladder from Pleasant River and explore nearby and you will see it!)

Hard: Rod is on a boardwalk towards the east of the docks.

Return to the homeless man. He unlocks the last part of the underground for you, so you can travel around Silent Hill faster and with less risk. You also get the following achievement:

Will Work for Food
Completed the Homeless Side Quest