A Connecticut grocery entrepreneur has his eye on expanding to a new town.
The possibilities are expanding for a Stew Leonard’s grocery store in the Milford/Orange area.
Leonard Jr. who is shopping for a site to build a new store in the Milford/Orange area, said it’s a lot like shopping for a “new home.”
“You have to look around town and decide if you can afford,” what you want.
Leonard has been interested in bringing his supermarket to the Orange area for about 30 years.
In the late nineties his family purchased a large parcel off Interstate 95 at Exit 41 and went through the land use process that developed into a years-long battle between warring factions in town, including hearings that drew hundreds of people and lawsuits.
While many town residents at that time said they did not want all the traffic the store would bring, Leonard’s team focused on the local tax revenue and number of jobs the business provides.
The Stew Leonard’s supermarket never came to be and years later the property was sold.
Leonard was quiet for a while on that issue, but said recently, he “loves the area,” and in recent years has shown renewed interest.
The grocer known for his flair and entertaining shoppers (think animatronics) who flock to the stores, opened a new location on the Berlin Turnpike in Newington around 2007, after extensive and expensive renovation at the former Caldor plaza there.
The now late Stew Leonard Sr. had opened the Stew Leonard’s store in Norwalk in December 1969. It was 17,000 square feet and carried eight items.
The store earned a spot as the World’s Largest Dairy Store according to Ripley’s Believe It or Not and also earned a place in the Guinness Book of World Records for having the highest dollar sales per square foot of selling space. Leonard Jr.’s siblings also have worked in the business.
Stew Leonard’s remains known for being a family-friendly destination with animatronics, such as a singing milk carton band, big plastic cows, and investment in the community.

Stew Leonard Jr., chief executive of Stew Leonard’s grocery and dairy stores. (Hartford Courant file photo)
Locations in both Orange and Milford are now in the mix of possibilities, including the site of the Raymour and Flanigan furniture store at 538 Boston Post Road and a couple of unnamed sights nearby on the Boston Post Road in Milford, he said.
“We have a lot of irons in the fire,” Leonard said. “We love Orange, we love the area. We just have to find something.”
He said people from Orange drive to their other stores to shop. The Boston Post Road stretch in the area of the Milford and Orange line also has Trader Joe’s and Whole Foods stores.
Most recently, Leonard had been eyeing the largely vacant Orange Plaza, 200 Indian River Road, where the now out of business Christmas Tree Shops store was located. Negotiations came to a halt over price.
First Selectman Jim Zeoli has said the Christmas Tree Shops plaza on Indian River Road is already zoned for retail, so Leonard won’t have the issues he had in the late 1990s and early 2000s, when he tried to open on Marsh Hill Road, an area where there is now FedEx center and an Outback Steakhouse, according to Zeoli.
The Indian River Road area there also has been developed, including with health care offices and housing.
Zeoli said Leonard had won all his zoning fights over 14 years but got tied up on environmental issues and finally gave up.
The family-owned chain, which began in Norwalk, has stores in Norwalk, and in Newington, Danbury, New Jersey and Long Island.
Leonard has said the family has decided they will open a new store every other year, though it has since slowed down. The strategy is “one that the family agreed on because we are a family business and we want our family to be part of management,” Leonard has said.

“My dad left us with quite a legacy,” Leonard has said. “And even though we are growing and expanding, we want to do it internally from our internal people; 80% of them are hired from within. We have this restriction on our growth because we want to do it with our team members that work at Stew Leonard’s now.”
