The boxes are often found in parking lots where residents drop items to be reused.
Some of the collection boxes are brought in by organizations outside of Winchester. Winchester leaders are now worried about where organizations could take these donated items once local residents drop them off.
"We've been approached by Blue Ridge Hospice in reference to noticing their donations are going elsewhere," says Milt McInturff, city council representative. "Through their own investigation they found out that a lot of local residents putting clothes into these drop boxes and they're leaving the area."
McInturff says collected items could be cleaned and sold whether they are staying in Winchester or going to other communities to help the needy.
Council members will vote in January on whether to require a permit for anyone dropping off boxes.
"The permits will not cost anything but an organization has to go through a process of identifying themselves and what the use of these boxes are for in order to get a permit for the future," says McInturff.
They will also vote on a possible fee increase for park users.
Winchester Parks and Recreation says it is necessary in order to keep providing quality service.
"It will allow us to recover more of our costs. For every dollar the city council gives to the city park, we return them 33 cents, so we're by no means a huge revenue generator, we're just looking to try to recover more costs," says Bradley Veach, director of Winchester's Parks and Recreation.
However, not all user groups are happy to hear about the news.
"The groups aren't happy that their fees are going to go up," says Veach. "I think that they understand that we're responsible for being good stewards of city tax dollars and when we've identified that, we're spending a lot of money in subsidizing non-residents."
McInturff and Veach say this new structure will place less of a burden on city taxpayers and more responsibility on user groups.
If approved, the new user group fee will take effect in July.