Visitors and residents alike will be asked to get out their plastic as they make their way around the City Walls to help ensure their longevity.
Cheshire West and Chester Council, in partnership with Big Heritage and Marketing Cheshire, is launching the trial scheme later this week to encourage admiring strollers to donate towards their maintenance and upkeep via three contactless payment devices.
However, it has been stressed the donation is completely voluntary.
The Walls - one of Chester's main tourist attractions with more than 2.5million visits a year - cost the council £600,000 a year to maintain.
The introduction of contactless payment technology will allow people to make donations if they wish by tapping their cards against devices at the amphitheatre, King Charles' Tower and Newgate Tower.
Guy Butler, chair of the Chester Growth Partnership, said: “Chester’s history and heritage is one of its key assets.
"It is vital that we maintain investment into the upkeep and development of these attractions if we are to capitalise on the significant potential they have to grow our visitor economy and enhance the city for residents.
"Introducing a voluntary donation system is a great way to ensure that visitors and residents can still enjoy Chester’s heritage for free, while having the opportunity to donate to preserve them for the future.”
The trial will run for three months, during which feedback will be sought from visitors, and be evaluated to assess its success.
Cllr Louise Gittins, cabinet member for communities and wellbeing, added: “Chester’s Walls are one of the city’s most recognised and visited attractions, and so it is vital that we explore ways to enable us to maintain the significant levels of investment needed to ensure that they are well maintained and safe for the 2.5 million people that walk and enjoy them every year.
“We know there is an appetite to make a donation as our visitors have asked in the past. However, the emphasis is for a donation only if they wish to do so.
"Asking visitors to donate is nothing new and increasingly commonplace amongst national museums and attractions.”