After they receive their money and McDonald's gift cards, hot chocolate, new socks and homemade hats are waiting for them outside.
"It shows the real meaning of giving, of sharing gifts and showing your emotional and spiritual awareness of the real reason for Christmas which is that Christ is born that day," Kevin, one of the attendees, told CNA.
"When you don't have much to give, you don't feel so jolly, but when someone gives you something, it makes you feel more generous," he added.
"It's people getting together and seeing old friends, (I feel) highly favored and blessed," said Wilma, another attendee.
Odalis Hernandez, a senior at Regis University who was helping hand out colorful, homemade knit hats from the students in the university's Father Woody program, said she was inspired to start helping people after seeing a movie about Fr. Woody.
"It's something that I wouldn't have done without the inspiration of someone like that," she said.
Lovey Shipp, a spunky nonagenarian who worked as Father Woody's secretary for several years before he passed away in 1991, still cherishes the many "Father Woody-isms" that she remembers. She has participated in every cash giveaway since its official beginning 28 years ago.
"Father Woody used to say, 'service is the rent you pay for the space you take up,'" she told CNA.
"He taught people with money how to give. It's not yours, it's by God's grace that you have it, you could be one of the homeless if he saw fit to do so," she said.
She encouraged anyone who desires to help the homeless this season to "keep an open mind and have your heart match. That's what Father Woody did."
"Just give," she added. "Give from the heart. And smile!"
(Story continues below)
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Mary Farrow worked as a staff writer for Catholic News Agency until 2020. She has a degree in journalism and English education from the University of Nebraska-Lincoln.
Perry West is a staff writer for Catholic News Agency. He graduated from Franciscan University with his bachelor's in English. Prior to his job at CNA, he worked in construction staffing and coffee.