Since May, Becky’s Diner on Commercial Street has been offering less in-person dining, but its takeout business has grown to account for more than a third of its daily sales. Michael Kelley / The Forecaster

PORTLAND — With winter approaching, Portland’s restaurants are heading into a “very difficult stretch,” says Hospitality Maine CEO and President Steve Hewins.

Of concern, he said is the state- mandate that dining rooms close at 9 p.m. and the ability of many restaurants to continue offering outdoor dining through the cold months.

To get through the pandemic, DiMillo’s on the Water introduced takeout meals and this week began delivery for the first time. Michael Kelley / The Forecaster

In an effort to make it easier to continue offering al fresco dining, the city is allowing restaurants to serve customers outside on public sidewalks, parking lanes and private property through Jan. 4. Typically outdoor dining is only allowed in the city into November.

Nelle Hanig, business programs manager in the city’s Housing and Economic Development Department, said as of mid-November, the city had received 55 permit applications for extended outdoor dining.

The city also has launched a Winter Business Sustainability Grant Program that provides up to $10,000 to “to assist Portland businesses with the cost of maintaining a portion of their operations outside through the fall and winter, due to the pandemic,” according to a release from the city. Funding can be used for furniture, equipment, heaters, coverings, barricades, lighting and other things necessary to maintain outdoor dining and retail as it gets colder.

Hanig said she has received a few requests for funding, but expects “a fair number of them” to come in as it gets closer to the Dec. 9 application deadline.

Hewins said the city’s new program and other COVID-related funding help, but restaurants may be weary of making large investments to stay open because of the uncertainty of how long or in what capacity they will be able to remain open.

“That is a huge factor,” he said.

Some financial help may be on the way. On Nov. 30, Gov. Janet Mills, citing the “additional challenges with the coming winter months,” announced a $40 million economic recovery grant program for restaurants, bars, tasting rooms, lodging and retail shops.

At Becky’s Diner, a fixture in the Portland restaurant scene for more than 25 years, Zack Rand, the general manager, and his staff are preparing for winter.

The hope, Rand said, is to continue outdoor dining on the second floor porch as long as it is feasible, along with takeout, delivery and limited in-person dining.

“This is the most unique situation we have ever been in,” Rand said of continuing to stay open during the pandemic.

The restaurant has eliminated nearly all counter seats, closed half of its booth space and has been operating at 30% to 35% of capacity for indoor dining since May. It has introduced delivery and relies more on takeout, which before the pandemic accounted for 5% of daily sales and now is upwards of 40%.

Rand said this winter his staff will continue to monitor state guidelines and adapt as needed in the hopes it “will allow us to continue to do what we have been doing and not have to take a step back.”

Becky’s is “doing everything we can from a safety and guideline standpoint to maximize things as long as we can, in order to get to spring and summer next year when things hopefully will look a lot better.”

Similarly, DiMillo’s on the Water manager Steve DiMillo said he will offer dining on the restaurant’s covered and heated lounge deck as long as possible.

“There is a fair amount of diners who want to still be outside,” DiMillo said.

Getting to this point has not been easy for restaurants.

DiMillo said business at the restaurant reduced drastically as the number of positive cases of COVID rose. In-person dining, he said, has been reduced to 50% of capacity and the restaurant had to find new ways to connect with customers by offering takeout for the first time. This week DiMillo’s introduced delivery through 2DineIn.

“We have never done that before, but that’s what diners are desiring,” he said.

The pandemic, DiMillo said, has caused the restaurant to reduce its staff from 200 people to less than 100.

He is optimistic, however, that the current trend of rising cases will reverse.

“We got our fingers crossed the numbers will go down and don’t increase to the point that indoor dining is shut down. I don’t think that will happen. I think things will eventually calm down,” he said.

Restaurant operators, Hewins said, tend to be resilient in a difficult industry and are used to operating in a challenging environment in which they have to handle and serve food safely, offer a creative menu, find ways to stand out against competition and manage and retain staff. All that becomes harder in the current pandemic.

“Our concern is many won’t make it on the other side,” he said.