South.

As I understand it, there are a large number of homeless that go to Miami (and other warmer climes) for the winter, and then catch a cheap bus in the spring and head back to Cleveland, Chicago, NY, Pittsburgh, etc.

At one point in my life, about 20 years ago, I volunteered time in a shelter (literacy stuff) and more than one of them told me that they made a circuit.

There’s a large expressway bridge near me and people live under it year-round. In the winter they have stacks of blankets 2 feet thick.

Only half a dozen or so stay under one bridge – the city breaks up any large or overly elaborate camp. This place lasted about a month, but that’s unusual for such “luxury”.

Chicago Tribune – Winter not all that delightful for homeless people

The homeless encampments of Chicago

The homeless encampments of Chicago – slideshow

I’ve been homeless for many years and I can say that the simple answer is: Somewhere warm and dry. People have all kinds of reasons why they stay in cities that snow and rain a lot during the winter, but I can only speak from my perspective. As @elbanditoroso said, going to warmer states is one option. And as @Call_Me_Jay said, under bridges when it’s raining or snowing or really anywhere there is a roof and some walls. Shelters are always filled up during this time as well. And since it is the holidays, a lot of the kids are accepted back home for a time. But yeah, warm and dry.

I’ve known guys that were veterans and they would go to rehab at the VA in the winter, and come out in the spring.

Some homeless go to local shelters.

Some head south (Florida, etc.).

Here in the Bay Area some cities open some temporary shelters for nights when it is cold or raining, often in the local armory. But the homeless don’t like it more than a shelter from the weather, because it is essentially a large room filled with cots and no privacy. Plus they can’t bring very much stuff inside with them.

Around here, they get in where they can fit in. Sometime s they tell me where they camp out at, I have been working with the outreach long enough that most trust me not to give up their location. If a somewhat cushy spot gets discovered then too many homeless end up there and sadly make a mess that draws attention then the city moves them out. There is a park that they hang with by day, I do not know of the cops enforce the curfew and make them leave at dark. They hang in the back of the Rite Aid loading dock, the train station, just about anywhere. The city knows it has a homeless problem but simply tried to farm them out to other cities that do have a homeless shelter. What is needed is transitional housing and retraining of the homeless to make them self-sufficient, somewhat like what Utah has done.

@Hypocrisy_Central Kudos to Utah.

I went outside and it was freezing, so it crossed my mind how do homeless survive such cold times. Thank you all for the answers.