Bridgnorth policing team said it was alerted to the vandalism spree at around 11.30pm on Monday, after receiving several calls from nearby witnesses who said windows and doors were being smashed.
A man was later arrested by officers, and is now in custody awaiting questioning.
The Crown Inn and The King’s Head were two of several properties damaged within the town centre.
Andy Corfield, manager at The Crown Inn, said he found a trail of blood along the High Street yesterday morning following the incident.
He added: “Basically we had a good night and locked up then went upstairs and I didn’t hear anything at all.
“I came down at around about 5.20am yesterday morning because we had a delivery, and one of our delivery drivers said ‘someone’s had a smashing time’, and pointed at our disabled toilet window.
“The King’s Head is by far the worst.
“We had some cones out on the side because we’ve got an issue with the roof, and one of the cones was in the middle of the road covered in blood.
“You could see a trail of blood all up the street, I don’t know how the person caused the damage.”
There are no security cameras on the side of the property, meaning the person responsible was not caught on CCTV.
Mr Corfield said the town rarely experiences similar incidents.
“The police have visited and took a statement, I’ve called my maintenance people to try and repair things as soon as possible,” he added.
West Mercia Police said it had taken several statements and urged any other businesses affected to come forward.
They are also asking witnesses to report any additional information to help inquiries.
PC Matt Picken said: “They caused some considerable damage to several licensed premisses, there were plenty of witnesses.”
Anyone with information can call 101.