The police began what they called a "dispersal operation, using minimum force" following the commemoration of a violent attack by masked assailants on supporters of the anti-government movement.
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Carrie Lam announced a platform for talks to help the China-ruled city find a "way out" after weeks of rallies. Protesters say Lam has not responded to demands, which include democracy, her resignation and an enquiry into the use of police force.
Beijing has taken an increasingly firm tone over the protests, accusing foreign countries, including the United States, of inciting unrest. China's embassy in Ottawa also warned Canada to stop meddling in Hong Kong's affairs.
At least 100,000 anti-government protesters joined a mass rally in Hong Kong, filling major thoroughfares in heavy rain in the eleventh week of demonstrations.
The biggest rally is expected to take place on Sunday on the main island.
The Hong Kong protests started as a peaceful rebuke of the government in April but have evolved into a direct challenge to Chinese rule over this former British colony.
China's ambassador to the United Kingdom said Beijing would use its power to quell Hong Kong protests if the situation deteriorates further.
Flights resumed amid heightened security at Hong Kong airport. By nightfall, police and protesters were again facing off on the streets, with riot officers shooting tear gas almost immediately.
Hong Kong is facing an economic crisis worse than either the 2003 SARS outbreak that paralysed the city or the 2008 financial crisis, leader Carrie Lam said.
As a three-day sit-in protest at the airport continues, several hundred families are taking to the streets to show support for anti-government demonstrations that are now in their third month.
Hong Kong faced major disruptions to business as general strike paralysed parts of the Asian financial centre, with more than 100 flights cancelled.
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