But with crowds numbering just a few hundred, the turnout was a reflection of the movement's loss of momentum after failing to push Beijing into allowing fully free leadership elections.
At the height of the 2014 protests, which lasted for more than two months, tens of thousands regularly gathered to demand political reform.
Yet despite the unprecedented rallies which garnered extensive coverage across the world, protesters were unable to force change.
Around 500 protesters gathered at the former main rally site in the financial district of Admiralty on Monday afternoon, jeering police who warned them not to block roads.
Rows of yellow umbrellas -- symbol of the pro-democracy movement -- several tents and a huge banner reading "I Want Universal Suffrage", lined the pavements.
The major highway through Admiralty was the focal point for the pro-democracy camp during the protests, when thousands of tents sprawled across the road.
"The authorities will still be against us, but that doesn't mean we will give up," said student leader Lester Shum.
Occupy Central co-founder Benny Tai called 2014 "one of the most important years in Hong Kong history".
"The Umbrella Movement... Was just the beginning for Hongkongers in their quest for democracy," he said.
Some protesters expressed their anger at the lack of progress.
"We have not achieved universal suffrage," a woman in her 30s, who gave her name as Lam, told AFP.
"Society is not geared to helping Hongkongers."
Lam had brought her young son to the gathering.
Others relaxed in the sun and browsed stalls of Umbrella Movement memorabilia.
One couple posed for pre-wedding photos, the bride-to-be in a strapless white wedding dress with a construction helmet -- often worn by protesters during the rallies.