"I wish they had a better attitude towards businesses," said Carpenter.
Back in 2003, the town gave business owners three years to get rid of the pole signs.
"Citizens enjoy Cary because of the aesthetics," said Cary sssociate planning director Ricky Barker. "Another step towards improving aesthetics is removing the pole signs."
A pole sign at South Hills Mall must also go. AnnMarie Rocheleau worries about her business if that happens.
"My business picks up every time my name is on that marquee," said Rocheleau.
The deadline comes at a time Cary is spending more than $10 million installing message pole signs of its own.
"(It's) our 21st century model, to help provide safety information and traffic flow information," said Barker. "It provides a great public service."
Carpenter said what's good for the town should be good for private businesses. At this point, he said he will comply and get rid of the pole sign that's been part of this landscape since the early 1900's.
The town says it will work with business owners even after the deadline. Businesses that don't show a good faith effort to get rid of the signs could face fines that start at $100 a day.
Cary actually banned the signs back in 1985. Engineers plan to work with business owners to remove them. There are about 16 pole signs still standing in Cary.