One participant named Chris held a sign saying, "To upgrade my impact."
"First I would just ignore and then I started giving money, but then I thought I need to do more," Chris told WBZ's Suzanne Sausville.
Ari Barbanell, executive director of Winter Walk, is working to alter the public's perception of homelessness.
"How do you think a little differently about homelessness? I mean homelessness can happen to anyone, it's not something that happens only to bad people," Barbanell said.
While Barbanell believes perception is a huge part of it, she also believes there needs to be change on the systemic level.
The event organizer's goal was to raise half a million dollars on Sunday.