The Timeless Charm of The Market on the Square in Downtown Cookeville

Owner Marlene Massa reflects on the hospitality, traditions, and loyal customers that shaped a downtown legacy

Nestled in the heart of Cookeville’s historic WestSide, The Market on the Square has become far more than a boutique. Over the years, it has grown into a gathering place filled with familiar faces, meaningful conversations, and traditions that continue bringing families back through its doors time and time again.

For owner Marlene Massa, the journey began unexpectedly. She first arrived at The Market on the Square as a tenant while the business operated under former owners Don and Cindy Calcote. Before long, Massa and Cindy became business partners, and shortly after, Massa stepped into sole ownership.

Since then, the family owned and operated store has continued evolving alongside its customers while remaining rooted in the same welcoming atmosphere that first made people fall in love with it. Today, that legacy also continues through Massa’s daughter and co-owner, Mara Grimes, whose involvement has helped bring a fresh perspective and another generation of connection to the downtown boutique.

Built on Relationships

“I contribute part of our success to having many different voices,” Massa shared. “The store is family owned and operated, so there has always been three generations of opinions going into the things we offer.”

That multi-generational perspective has allowed the store to stay fresh while still maintaining the small-town charm customers have come to love. Massa says creating a welcoming experience has always mattered just as much as the products themselves.

“We are happy to be here and we want you to be happy here as well,” she said. “Enjoying your time in the store is of utmost importance.”

Over the years, The Market on the Square has become woven into countless milestones and memories throughout the Upper Cumberland. From baby showers and birthdays to weddings and graduations, Massa says the greatest blessing has been watching families grow through the years.

“We have seen some kids receive their first gift and also their wedding gift,” she shared. “We have become a meeting spot for girls’ weekends and a ‘can’t pass through Cookeville without stopping’ spot.”

A Downtown Tradition

Massa credits much of the store’s longevity to loyal local support and a continued commitment to customer service.

“Customer service. Customer service. Customer service,” she emphasized.

Today, The Market on the Square remains more than a boutique. It is a gathering place, a tradition, and a reflection of the relationships that continue to shape downtown Cookeville.

“The Market on the Square’s legacy and mine are the same,” Massa said. “Work hard, be humble, and treat people with respect. Success comes when you do those things.”

For more information on The Market on the Square, visit their website or their business listing on our website.

_{By Chelsea Dartez, photography by Emily Armstrong}