Andy Preston and Richard Lewis joined Middlesbrough Council Street Wardens on patrol in the Gresham area in the centre of town.
The two spoke to numerous residents, including a couple who had lived in the area for more than 50 years and a family who were originally from Slovakia, as well as business owners and visitors to shops on Parliament Road.
Residents spoke of the proud history of the area but also highlighted issues blighting people's lives.
Mayor Preston has made tackling crime and anti-social behaviour in TS1 a top priority since his election in May this year.
A recruitment drive is now underway for an additional 23 Street Wardens for the town, current Street Wardens have been given additional powers, Community Enforcement Vehicles with CCTV have been introduced and a consultation has been held on the introduction of a Public Space Protection Order.
Mr Preston said: "Defeating crime and anti-social behaviour in Central Middlesbrough is a tough task and one of the first things we have to do is fully understand the communities and the issues they face.
"The Chief Constable has given some of his valuable time talking to residents and business owners and encountered some local characters.
"We met a man in distress, someone gave us a tour of their home, people spoke about a lot of the problems they face. It's a big challenge but we can make things better."
Chief Constable Richard Lewis said: "A great privilege of my job is hearing directly from communities about the challenges they face and what we can do to improve their lives.
"It is clear that there is so much we can do together as police and council to improve the lives of people in areas such as Gresham. You have my commitment to personally invest energy and resources to this cause.
"Thank you to Andy Preston for facilitating the joint patrol and the time spent with the impressive Street Wardens who do such a great job for the community."