The project will offer many things new to the eye such as public restrooms, new underground features, a splash fountain and new entrance ways.
While there have been concerns of possible inconvenience, Winchester's new downtown manager says locals can still go where they need to.
"You can easily go to your favorite restaurant and your favorite shops there's really no restriction to that. There's walls protecting people from the construction but again still allowing people to look at it," says Jennifer Bell, new downtown manager.
In celebration of this project, city officials gathered to show support for the businesses that will remain open during the construction.
"I'm very excited. We've planned on this for such a long time and it's finally here and the progress has been amazing; it's been great. Like the paper said the other day, they have really hit the ground running," says Elizabeth Minor, mayor of Winchester.
The Walking Mall has always been the "it" place for locals and visitors, offering a fair share of fine dining, shopping or a brisk walk.
"People are starting to invest in the city especially downtown and they'll look at this as another opportunity to be where the city is investing in our future," says John Willingham, city council vice president.
"I look at our downtown as any community sort of like you do your living room and so when your living room needs a little cleaning, what do you do? You clean it up, especially before you invite company in," says Dale Iman, city manager.
For those navigating downtown, Boscawen will be closed between Indian Alley and Cameron Street and will reopen when the intersection is complete.
The project is expected to be completed from end of May to April.