Protesting under the banner of India Against Corruption (IAC) and against the alleged irregularities in the coal blocks allocation, the crowd tried to march to Singh's residence twice, but was detained on both occasions.
The first attempt at 6am caught the police off guard.
"Arvind Kejriwal and Gopal Rai reached near PM's residence with a few supporters while IAC member Sanjay Singh went to Nitin Gadkari's home at Teen Murti Lane. They were detained and taken to the Mandir Marg police station," said a senior police officer.
As news of the detentions spread, the protesters headed to the police station and staged a dharna. Kejriwal was released at 8am.
"What wrong are we doing? We are just sitting quietly on the footpath. At least we should be told why we are being detained," Kejriwal said.
"When Raj Thackeray takes thousands of his supporters for a protest without permission, the police provide protection. What kind of politics is this?"
"We will gherao again. We want to send a message to the Congress and BJP," he said.
Once the protesters headed to Jantar Mantar, Kejriwal announced his intent to picket the residences of Singh, Gadkari and Gandhi.
At 12:45pm, defying police orders, more than 1,000 supporters began marching.
They broke through five barricades in front of the Parliament Street police station and split strategically in several directions.
At 10 Janpath -Gandhi's home -the police used water cannons to disperse the aggressive crowd.
Slogans were shouted outside the homes of politicians and several name plates, including the one at former telecom minister A Raja's residence, were broken.
The situation deteriorated near the PM's house on Race Course Road, forcing the police to cane the protesters and fire several rounds of tear gas.
Police said Kejriwal, who was detained for the second time at 2pm, was released at 3.45pm.
Other IAC members were taken to the Parliament Street police station, where 500 supporters remained lodged till late evening.