Courtney Bass was riding shotgun in the black van last week as it pulled up next to people resting on the sidewalk along Oxford Street in Portland.

As soon as Bass got out one of the women in the group held up a clump of tangled hair.

“Look at this?” said Kaylee, who would provide only her first name.

She handed a brush to Bass, who got to work gently trying to unsnarl Kaylee’s blond hair. As she did, Brooks Ross, the van’s driver, loaded a wagon with bottled water, peanut butter-and-jelly sandwiches and other food and began handing them out to people scattered around the city shelter.

Bass and Ross are outreach workers for Milestone Recovery, a Portland nonprofit that provides people on the streets with shelter and substance use treatment. Like city officials and other service providers, they’ve seen an increase in the number of unhoused people, including those going without shelter, as the nights grow longer and colder.

Kaylee, 28, said she hopes to get clean so she can one day get back her 3-year-old son but she hasn’t been able to find a sober living bed.


She had spent the previous night sleeping on the sidewalk near the shuttered day shelter and soup kitchen operated by Preble Street, another nonprofit social service agency. She’s been doing that for six months, she said, using trash bags and ponchos to stay dry.

“It was really cold,” she said of last week, when temperatures dipped into the 40s. “My friends and I huddle together and try to keep each other warm.”

This will be a winter of uncertainty for those living on the streets, with shelters continuing to operate at reduced, pandemic capacity and federal funding that has paid to put some unhoused people in hotel rooms set to expire at the end of the year.

Courtney Bass, left, and Brooks Ross, outreach workers with Milestone, walk down Oxford Street in Portand on Friday, pulling a wagon with water and sandwiches to hand out to homeless people. Gregory Rec/Staff Photographer

The hotel rooms have helped a lot, but they’re temporary. And many people are still sleeping outdoors, either due to circumstances, choice or simply not knowing where to find help. Some area service providers say they lack the staff to reach out to all those in need and connect them to resources.

The city continues to be without a day shelter since Preble Street closed its resource center in 2020 because of the pandemic. And reduced hours elsewhere, at places such as the public library, have left the unsheltered with fewer options to get a break from being outside.

With the hotel funding expiring, plans have to be made to move people out of the rooms, but the chances to offer them other shelter are few in an area with an affordable housing crisis.


State officials say they plan to use federal emergency rent assistance to continue using hotel rooms when needed, as is likely in Portland. But local service providers say that while everyone is doing what they can, they still can’t meet the growing need.

“We’re starting to see some more folks outside now, unfortunately,” said Joseph McNally, Milestone’s director of homeless services. “We’re obviously concerned. There is still not a day space for folks to go, so that’s really a challenge. … There’s not a place where people can easily get out of the elements.”

Kaylee said she’s been on a waiting list for a housing voucher for the last three years. She stayed for a period of time in a hotel but “circumstances changed.”

But even inside, she said, “Sometimes I would almost feel guilty sleeping in a warm bed, when my friends are down here freezing.”


It’s unclear exactly how many people are going without shelter in Greater Portland.


Through its PATH program (Project for Assistance in Transition from Homelessness), the Opportunity Alliance, a Portland-based nonprofit, conducts outreach in York and Cumberland counties. About 125 people are receiving help from PATH, up from 80 at this time last year. The majority of those individuals are in the Portland area, including about 50 without shelter.

“We’re going in a worrisome direction,” said Joseph Everett, the organization’s president and CEO. “There just doesn’t seem to be any end to the need.”

Preble Street also runs a four- to five-member outreach team called the Street Outreach Collaborative.

Spokesperson Jennifer Tibbals said in an email that the team served 236 people – most of them unsheltered – from July 1 to Sept. 30 in Portland. She said last winter the agency helped 81 people, who otherwise would have been sleeping in the woods or on the street, access emergency shelter. The nonprofit’s outreach efforts served 609 people from July 2020 through June 2021.

“Some of the biggest barriers clients are facing are a lack of affordable housing to move out of homelessness and long wait lists for treatment for substance use disorder, which we have seen an increase of since the pandemic began,” Tibbals said. She said many other Preble Street staff besides its outreach team go out on the streets along with partners at Grace Street Ministries and the city of Portland “to bring services and casework to clients where they are at.”

Kabir Geiger prepares to ride his bicycle down Oxford Street in Portland on Friday. He said he’s been sleeping outdoors for 10 years, and “It’s killing me physically.”  Gregory Rec/Staff Photographer

Kabir Geiger, 43, was riding his bike along Oxford Street when he grabbed a sandwich from Milestone outreach workers. He said he’s been sleeping outdoors for 10 years, because he keeps getting kicked out of the shelter for what he calls minor offenses – having a hypodermic needle or not keeping his antidepressants in a bottle.


Living on the street is tough enough, Geiger said. Being judged makes it worse.

“You would have to experience this to understand it,” he said. “I’m so desensitized and traumatized. It’s killing me physically. I’m falling to pieces.”


One night in January each year communities across the nation are required to conduct a point-in-time count of people experiencing homelessness in order to continue receiving federal funding from the U.S. Department of Housing and Urban Development. This year’s count has not been finalized.

From 2019 to 2020, the statewide homeless number remained relatively flat – 2,106 in 2019, 2,097 in 2020 – but the share of unsheltered people grew by over 48 percent, from 95 to 141.

Over that same period nationally, the number of people experiencing homelessness increased by 2.2 percent, to 580,466, while the number of unsheltered went up by 7 percent, to 226,080.


Although Maine’s 2021 count is not yet official, MaineHousing, which oversees emergency shelter programming, said 1,097 people were homeless in shelters in Maine this year.


Portland — Maine’s largest city — provides services for the bulk of the statewide homeless population. The city operates a low-barrier adult shelter on Oxford Street and a family shelter on Chestnut Street, both in Bayside. But outreach to people without shelter mostly comes from area nonprofits. And there also are private shelters.

City officials say they are now serving 850 individuals in city-run shelters and hotels, including 343 single adults and 507 individuals in families, about 90 percent of whom are seeking asylum.

Aaron Geyer, the city’s director of social services, said the city recently tried to hire four outreach workers to search out unsheltered people and try to connect them with services, but no serious responses have come in.

“We’ve done some checks of the RVs and some of the folks sleeping in cars and have had some success in connecting some of those folks to the shelter and hotels,” he said.


Geyer said the city has only enough staff to provide support services to people staying in the shelter or in hotels under contract with MaineHousing. It doesn’t provide support to people staying in hotels funded by General Assistance.

Dillan Libby, 31, standing outside the Comfort Inn in South Portland, says he is grateful to have a hotel room to stay in, after living out of his car. Gregory Rec/Staff Photographer

Dillan Libby, 31, was among those staying in a South Portland hotel paid by General Assistance last week. Libby said he had been sleeping in his Honda Civic since January, when his husband kicked him out because Libby was using drugs.

He’s been in the hotel for two weeks and said he is no longer using heroin. He hopes to regain stability.

But he will have to do it on his own.

“My goal is to try to get a job, save up some money so I can get another car and maybe go back home to my husband,” he said.



MaineHousing says its used federally funded hotel rooms not just for emergency shelter but also as pandemic isolation and quarantine space.

Denise Lord, the senior director for strategic initiatives at MaineHousing, said that efforts to move people out of the hotel rooms and into stable housing have worked better in smaller, more remote towns than in places like Portland, which has large numbers of homeless people and a severe shortage of housing.

“There’s virtually no affordable rental properties,” she said.

The agency had 253 hotels rooms under contract in Bangor, Warren, Lewiston and Portland during the summer of 2020. The bulk – 184 – were to quarantine and isolate after coronavirus exposure, while 63 rooms were used for emergency shelter. The agency also supported 120 congregate emergency shelter beds in an armory and gymnasiums in Portland, Lewiston and Presque Isle.

As of Wednesday, the agency had 298 hotel rooms under contract, with all but 81 providing emergency shelter. That includes 149 hotel rooms in South Portland for use by the city of Portland. 



In Portland, Preble Street’s decision to close its day shelter at the onset of the pandemic came after reductions in hours dating to 2018.

Some people looking for other places to go wound up in Deering Oaks park.

The city’s Oxford Street Shelter is open 24 hours a day to people who stay there – but the pandemic has cut capacity in half, from 154 people to about 75.

Over the summer, city officials offered nearly $260,000 to any social service agency willing to open a day shelter, but received no response. Two providers — Amistad and Milestone Recovery — explored a possible partnership but were unable to find an affordable location on the peninsula, where the need is greatest.

The Portland Public Library has long been a place for people to escape the elements, but it was closed for a long time due to the pandemic. Now the main library is open to the public for a few hours on Monday through Friday.

The lack of day space has made mobile outreach efforts even more important. Last week, Ross and Bass, the Milestone outreach workers, walked from the city shelter to Preble Street to Deering Oaks and back, handing out water and food and checking in with people.


Jonathan Walsh, 35, said he’s been sleeping outside near Preble Street for the last four months.

“These guys are cool,” Walsh said of Bass and Ross. “They’re not here to judge us. They’re here to help. They just talk to you like you’re a normal person.”


Preble Street is planning to convert its former day shelter into an overnight shelter with 40 beds. It’s intended to serve people who are currently unsheltered. The project was approved in January, but the agency did not receive its building permits until late August. City officials attributed the delay to getting information from Preble Street.

Preble Street’s executive director, Mark Swann, who was not available for an interview last week, had originally estimated it would take only six to eight weeks to complete the project. He gave an update through a spokesperson but did not say when the shelter would open.

“Opening the Wellness Shelter to clients is a top priority for Preble Street, and we are moving forward as quickly as possible,” Swann said. “As with most building projects since the pandemic began, we have been faced with many unexpected delays, including construction and supply schedules. We look forward to the day we can open the Wellness Shelter doors and offer safety, warmth, and 24/7 case services to people experiencing homelessness and complex health and behavioral issues who cannot access any other shelters.”


The city, meanwhile, also is working to build a new 208-bed homeless services center in the Riverton neighborhood. The project, approved last month, would include beds rather than the current city shelter’s thin floor mats, as well as a medical clinic, soup kitchen and a day space for guests. But a citizen referendum on the November ballot aims to stop it, calling for smaller shelters.

Michael Bisson, who was in Deering Oaks in Portland on Friday, has been homeless for over 10 years and says he’s dealing with stage four stomach cancer. Bisson is now staying in a hotel in South Portland with his girlfriend but comes into Portland to spend time with his friends in the homeless community. “I’ve got no family other than these guys out here,” he said. Gregory Rec/Staff Photographer

Until there are more shelter and housing options, Michael Bisson, 48, said he will keep doing what he can to survive.

Bisson said he has spent 14 years living on the streets of Portland. He said he’s not educated and served time for involuntary manslaughter, stemming from a fight when he was younger.

He was recently diagnosed with stage 4 stomach cancer and had spent the previous three nights in a South Portland hotel room. But he said he felt isolated there and didn’t have money for bus fare to get back into town.

“I’ve got no family other than these guys out here,” Bisson said of his friends on the street.

During cold nights, Bisson said, he walks around and does push-ups and sit-ups to stay warm. He does not plan to undergo cancer treatment.

“I don’t usually sleep – hour here, hour there. I just roam around,” he said. “I figure I will get plenty of sleep soon enough, you know what I mean? I have stage 4 cancer. I’ll sleep soon enough.”

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