After 500 days on the picket line, striking Chronicle Herald workers in Sydney say their prospects look "bleak" and are not optimistic that a settlement will soon be reached.

"It's definitely a milestone. And one that we hoped we wouldn't have reached," reporter Erin Pottie said on Monday.

The Herald is Canada's oldest, independently owned newspaper. Unionized newsroom staff have been on strike since Jan. 23, 2016.

Fifty-three workers across Nova Scotia remain on the picket lines. Pottie and Tom Ayers are the two remaining striking Herald workers in Sydney — a third left the area to take other work.

"We still get honks of support on the street from people driving past," Ayers said.

"People walking past stop and ask us how we're doing and offer to buy us a coffee or something. And they try to buck up our spirits. It helps for sure. But the company just wants to keep us out."

Ayers said Herald management intends to close the Cape Breton bureau when the strike ends. (Holly Conners/CBC)

In April, the owners of the Herald purchased 28 Transcontinental Inc. news publications across Atlantic Canada, including the Cape Breton Post.

"Regardless of the profit levels of all those papers, they've now got cash flow that means they can afford to keep us out longer. So it's not looking good," Ayers said.

Cape Breton bureau

Even if a settlement is reached, the company has told the union it intends to close the Herald's Cape Breton bureau, said Ayers.

"That's not good for journalism in Cape Breton. It's not good for the economy in Cape Breton," he said.

Herald management declined an interview request from CBC. The paper has been using replacement workers.

Management has argued it needs to cut costs. The union has said it is willing to accept some cuts to wages and vacation time, but that the paper is seeking too many concessions.

The national union representing striking Herald employees is in the process of filing an unfair labour practice complaint against the company.

"We were waiting for the company to get back to us, hoping that there would be [further] bargaining," said Martin O'Hanlon, president of the Canadian chapter of Communications Workers of America.

"As of last week, the company basically told us they're not interested in getting back to the bargaining table. So we will be proceeding as we need to do."