Prison officer John Darwin, 51, was seen entering the sea in the Seaton Carew area with his kayak at 0800 GMT on Thursday.
The alarm was not raised until 2130 GMT when it was reported he had failed to arrive at work for a night shift.
On Friday afternoon the search for Mr Darwin moved southwards from Seaton Carew towards Saltburn.
"
If a canoeist loses his oar... he is at the mercy of the sea and currents
"
Dave Cammish, Redcar Lifeboat
Five RNLI lifeboats, two coastguard rescue teams from Hartlepool and Redcar, a police fixed-wing aircraft with heat-seeking equipment and teams of police officers have been involved in the search.
Dave Cammish, deputy landing authority for Redcar Lifeboat, said they had searched a 62 square mile area from Hartlepool in the north, to Staithes in the south and up to ten miles out to sea during the night.
Mr Cammish told BBC News Online: "At 0115 GMT a double-ended paddle, used by people in this kind of kayak, was retrieved from the sea near North Gare, not too far from Seaton Carew.
"If a canoeist loses his oar and cannot retrieve it, he is at the mercy of the sea and currents and has to sit it out until he is rescued.
"Normally, these people wear the right sort of protective clothing and we hope this is the case in this instance.
Shoreline search
"We have got to remain optimistic that he is found.
"Our search got under way at midnight and we searched throughout the night, covering a 62 square mile area.
"We relaunched at 0500 GMT this morning with a new crew."
Cleveland Police officers carried out a shoreline search.
A Cleveland Police spokesman said: "Cleveland Police, in conjunction with the Humber Coastguard have been carrying out a search of the Tees Bay area from Hartlepool to Redcar for a missing canoeist."