North Yorkshire Police is investigating the West Yorkshire suspects relating to thefts in the Whitby and Humberside areas.
Four of the five suspects were arrested on the A171 towards Scarborough at around 1am on Sunday.
Officers from the Roads Policing Group and the Scarborough Rural Taskforce were alerted to the incident just after midnight following reports of tools being stolen from a vehicle parked near the Flask Inn, just off the A171 between Whitby and Scarborough.
A police operation, which included the use of a tyre-deflating stinger device, was carried out to stop a blue Vauxhall Astra car.
A white Peugeot Expert panel van, driven by the fifth suspect, was stopped by police on Castle Road in Whitby just before 1am.
The men – a 49-year-old and 28-year-old from Bradford, a 28-year-old from Leeds, and a 28 and a 32-year-old from Morley - were arrested on suspicion of being involved in a conspiracy to steal from vehicles in North Yorkshire and Humberside.
High-value items seized by the police included various tools and an off-road motorcycle.
Extensive enquiries are ongoing into the incident and other suspected offences.
The men have been released under investigation while the case continues.
Anyone with information is asked to call North Yorkshire Police on 101, select option two, and ask for the Scarborough Investigation Hub.
Crimestoppers can be called anonymously on 0800 555111.
Quote reference number 12170069010 when providing details about this incident.