Works to repair the stone setts in Red Lion Square are expected to begin during summer 2022.
Cllr Richard Davies, executive member for highways, said: "We originally installed Yorkstone setts in Red Lion Square in 2007.
"However, these have been moved about, lifted out of place or broken over recent years as vehicles have moved through the square.
"To save money, time and disruption in the future, we are looking into replacing the current stones with thicker setts and a stronger underground foundation.
"This would not only make the surface more robust by preventing cracking and shifting of the stones, but also maintain the current aesthetic of the square and Stamford generally."
The county council has identified Eurovia as its preferred contractor for the Red Lion Square improvement scheme, which is currently in the detailed design phase.
If taken forward, a specific start date for the project would be confirmed closer to the time, but the scheme is expected to take up to five months to complete (subject to suitable weather).
Various one-way systems and short duration road closures would be place during the works in and around Red Lion Square. Details are still being confirmed with the contractor and will be made available and published in advance of starting.
Cllr Davies added: "As with any other major improvement project, there would inevitably be some disruption on local roads once work is underway.
"However, I want to assure residents and businesses that, if taken forward, we'll be doing our very best to keep traffic moving and to maintain access to all shops and businesses.
"We'll also work to ensure local roads are fully clear ahead of and during the 2022 Burghley Horse Trials."
The project is set to be reviewed and discussed by the county council’s Highways and Transport Scrutiny Committee on Monday 25 October before a decision is made.
The estimated £1.4m maintenance and repair scheme is being fully funded by Lincolnshire County Council.
For more information about this and other major highways projects, visit www.lincolnshire.gov.uk/majorprojects.