C.Ann, You can call the any of the three main cities missions near you. They actually have plans already to get items out there. They've been doing it for years and they do it best. They work with the homeless every single day, and know most of the homeless by name. When the shelters are full, and it's going to be cold, they turn their eating areas into shelters. They have tons of info on individuals, and know which of them will resell what you give, and which can use it, and they get the items out to them. At the nighttime free meals (which anyone can attend..we have the homeless, the lonely , even the occasional engineer that has no family and just wants to talk with another person) they have available coats, mittens, blankets, etc. No questions asked, you need them, you take them. These items really do go out to those that need them. A great thing just started during some of these meals is a free medical evening. Volunteer nurses and doctors evaluate, treat and dispense meds, no charge.
A Diser here sent me a big box of Disney soap (that she collected at her many trips to Disney) that I gave out during evening meals to kids..and my last trip I asked housekeeping for some to take back, and all I had to do was supply the name of the mission/phone number and they gave me more. Some of these kids that are living in cars and sheds don't have the simplest item..soap. One little girl told me she hated to go to school, because she was never clean. Her mom and I have talked and it is just unbelieveable how people end up like they do (our local mission recently opened a shelter for females and their children if they have them. Most shelters are men only, so this is wonderful).
All the kids that show up start school with a backpack full of school supplies. At Christmas they get several new toys provided by toys for tots and the local motorcycle club.
So there is lots of help needed and taken in our local area. There is nothing more humbling than working the nightly meals (they are always looking for volunteers..and it's a great community service program for kids, and they also serve the meals). Makes me so grateful for all I have. So many of those that come in have so little, and we have time to sit with them and talk with them if we want, and the kids just make you so sad..what little they are thankful for.
You need to ask to be referred to an agency that has a street outreach program -- most major cities (and some smaller ones) do. You can make it clear that your donation is for people who are unwilling or unable to come in to shelter. For instance, we have outreach vans that are on the streets 365 nights a year. By the way, there are shelters that go over capacity and have people sleeping in their lobbies during the winter -- not ideal, but better than freezing. Not every provider can do this, but generally those that are able do.
Maria