My night as a homeless person - 10/31/2025

As part of our World Homelessness Day event held on Carroll Creek on October 10, Frederick Chief of Police Jason Lando and I agreed to stay up all night on the Creek. We even called the event Chief Lando’s “All-Nighter” to raise awareness for homelessness in Frederick County.  I was there to offer support to the Chief and to be there in case he had to leave for an emergency. The event was co-hosted by Advocates for Homeless Families and Beyond Shelter Frederick. 

After speeches from dignitaries including Chief Lando and Chamber of Commerce CEO Rick Weldon, writing messages to homeless folks on our “board of hope,” a tour of Wade Millyad’s amazing Fresh Step Laundry van to aid the homeless, filling the Chief’s cruiser with personal care items to be delivered to the shelters and Lynnette Cary leading a moving candlelight vigil to honor Fredericktonians who died due to homelessness in the last few years, the Chief and I settled in for the night. 

Because the optics of a chief of police asleep on the sidewalk in full uniform are not good, the Chief elected to spend the night in his cruiser (as many homeless folks do in their cars.) Restless, he sometimes walked the creek taking photos and even went out to assist on a call, but always came back. I, on the other hand, brought a reclining lawn chair, a heavy coat, hat, gloves and two blankets, determined to spend the night out in the elements, which I did.

The night wasn’t particularly cold – the low was 42 degrees at 4:00 a.m. – but I was cold nonetheless and had trouble adjusting. I finally figured out that if I pulled my blankets up over my head to form a tent of sorts, I could use my breath to warm the air around my body, except for my feet. This had the added benefit of blocking out all the ambient light surrounding me. The downside, of course, is that I could not see what was happening around me. And boy, did things happen around me.

Shortly after 1:00 am when the nearby bars closed, 20- and 30-somethings poured out onto to the street and onto Carroll Creek to continue partying. They had absolutely no regard for this “homeless person” or anyone else in the nearby condos, for that matter, trying to sleep. They hooted and hollered like they were still in the bar. One young lady even lowered her pants to moon me from about 30 feet away. I was grateful they did not overtly try to bully me. After about an hour, they finally departed.  I was left wondering if real homeless people were subjected to this type of thoughtless behavior from young, tipsy people.

I made the mistake of leaving a little food, beverages, coolers and a folded-up canopy out in the open and all around me as I tried to sleep. These items were used during the event, and I planned to return them in the morning. All throughout the night, however, I was visited by homeless people who couldn’t resist the free offerings. I could hear them trying to be quiet and not wake me, but somehow the light rustling made it even more unsettling. I couldn’t see a thing in my makeshift tent, but I wanted to be safe so I looked up every time. Most did not say a word when our eyes met, just taking what they wanted. Others politely asked before they took. In my half-asleep stupor I told one fellow to take what he needed. He proceeded to take my $75 canopy. I meant for him to take food and beverage, of course, but could not protest, I’m sure he needed the canopy more than me.

All this activity made sound sleep impossible. I was left wondering how real homeless folks do it. Most times, they are surrounded by all their worldly possessions, worrying that someone may come and take what little they have. How unsettling and frightening that must be. I will never look the same way again at a homeless person snoozing in broad daylight. I now know they are not lazy, but just catching some rest when they can.

I learned that sleeping in a lawn chair even if it reclines is not easy. I found out quickly that what is comfortable for an occasional weekend nap is not so comfortable for sleeping in all night. But the alternative was the cold, hard concrete, so I stayed put. The next morning when I arose for good, I was a bit stiff.  As the day wore on, I was really hurting. Homeless folks are physically hurting, too. I was told by folks who know, homeless people are ingenious about their sleeping arrangements. Still, I couldn’t help wondering about the efficacy of having all our park benches built with armrests down the middle so folks can’t recline. I can see both sides of this argument, but it sure seems like one more unneeded indignation for those who just need to sleep. 

At one point during the night, because I couldn’t sleep, I took a long walk on the Carroll Creek promenade to its terminus near the fairgrounds. Besides the eerie stillness that you never have during the day, I only saw one homeless individual asleep, and he was in a wheelchair. So, I guess the foreboding benches have served their purpose and chased homeless folks elsewhere.

I know you may be thinking, “why don’t homeless folks just go to a shelter?” I’ve had more than one tell me that shelters are often loud and dangerous. The rules and sheer breadth of humanity crowded into such close quarters are more than some homeless folks can handle. Better to sleep on your own in a tent, vehicle or park bench they tell me.

I’m under no illusion that my one night spent outside gives me any insight into what homeless folks contend with every day. It must seem overwhelming and paralyzes many into inaction. My night was tough, but at least I could look forward to a hot shower, a good meal and restful sleep in my own bed the next day. Homeless folks can allow themselves no such thoughts.

One good thing did come from all this.  

In the morning as the Chief and I and a few others enjoyed some coffee and donuts provided by well-wishers (we left almost all the food and drink behind to be enjoyed by others) we could faintly hear a cry for help coming from the other side of Market Street on the creek. We all started running and finally found a homeless person, Thomas, on the ground beside his wheelchair laying on the ground in a little alcove near Frederick Social. He could not get up. He explained that someone wheeled him over to this spot for the night, but after he fell asleep on the concrete, his arthritis got the best of him. After gently picking him up and plying him with coffee and donuts back at our outpost, he insisted he be taken back to his “spot” on the creek so he could bum a cigarette and get a light.  

His story is one that is probably all too common. 

As a younger man he used and sold cocaine and spent 20 years in prison for it. When he got out no one would hire him so he took to the streets. As he aged, his arthritis got worse and now makes it hard for him to wheel himself up the hill to the shelters. So, he stays outside. He has a son and sister in Florida who might help but they lost touch during his incarceration, and Thomas doesn’t know how to contact them. He told me matter of factly, “If I’d have known how all this would turn out, I wouldn’t have done it.”

As bad luck would have it on that cold morning, a Frederick Police officer (not the Chief) served Thomas with a summons to appear in court for indecent exposure. Some weeks back he relieved himself in front of bystanders who reported it. I implored Thomas to use his day in court to ask for help locating his family. I don’t know if he will do that, but I hope so. It’s hard for ordinary citizens like me to know how to help. It seems the best we can do, that is not a temporary fix, is to put them in touch with those who can help.

Thomas is an example of how the system has failed. To be sure, he may not be helping himself as much as he could and may have even been playing me, although to what end I’m not sure. I couldn’t help thinking that a tiny home on church-owned property or a comfortable ground floor apartment that only demanded 30 percent of his social security each month would give him his dignity back and a chance at a semblance of a modest life. In both cases, we know that intensive support will be needed, but that system is already in place in Frederick and could help Thomas. All that is missing are the homes.

Gary Bennett is a board member for Advocates for Homeless Families and an appointed member of the Affordable Housing Council o Frederick County. He was the principal organizer of “Chief Lando’s All-Nighter” to raise awareness of homelessness in Frederick.