Leonard “Red” Bolling in the early days of Red’s Dairy Freeze on Cottage Road in South Portland. Contributed / Red’s Dairy Freeze

On the average week, 300 gallons of ice cream and 50 pounds of sprinkles pass through Red’s Dairy Freeze and into the cones and bowls of their loyal customers.

A lot has changed at the South Portland shop since it opened 70 years ago this summer, when small vanilla cones went for a nickel, shakes and sundaes were a quarter, and a banana split cost 50 cents. Yet, there is a lot that has stayed the same.

Leonard “Red” Bolling started the South Portland ice cream shop as part of the Tastee-Freez franchise in 1952. In 1965 he ditched the franchise and decided to go out on his own. Red’s son, Chris Bolling, and daughter-in-law, Alison, took over operations in 1991 before Red died in 2001 and his wife, Hazel, in 2008. Now, Red’s granddaughters Laura Gregoire and Sarah-Jane Josef work at the shop.

Leonard “Red” Bolling opened the popular South Portland ice cream shop in the summer of 1952. Contributed / Red’s Dairy Freeze

“This is all we’ve known,” Gregoire said. “This is where we grew up and it just feels like this is how it should be.”

Starting with just vanilla ice cream, Red’s now serves dozens of flavors and sweet treats, such as the top-secret shake (Psst! It’s not on the menu, but it’s “the Boston.”) and limited-time-only Strawberry Maxwells, made with fresh strawberries from Maxwell’s Farm in Cape Elizabeth. This summer, Josef said, they sold out of Strawberry Maxwells in just 2½ days.

But the South Portland family-owned business has had its challenges. In May 2010, an electrical fire shut down Red’s for a year. South Portland residents,  especially kids, gave the Bolling family a much-needed boost while they rebuilt.


“There was a lot of community response,” Gregoire said. “There were kids who left us notes and get-well cards.”

Sarah-Jane Josef, left, Laura Gregoire and Chris Bolling at Red’s Dairy Freeze in 1989. Contributed / Red’s Dairy Freeze

“There was a baggy of quarters at one point, that said ‘these are for the rebuild,'” Josef added.

A decade later, the pandemic posed another challenge. Like businesses around the world, Red’s found creative ways to navigate the infamous summer of 2020.

“We put out brownie kits –’Here are your two quarts of vanilla, six brownies, sprinkles and cans of whipped cream, cash only, put it in the bucket,'” Josef said.

Laura Gregoire, left, Sarah-Jane Josef and Chris Bolling. Contributed / Red’s Dairy Freeze

Over the decades, Red’s has become much more than an ice cream shop.

“It’s hard to think of a landmark more popular than Red’s Dairy Freeze,” said Kathy DiPhilippo, executive director of the South Portland Historical Society, adding that it’s commonly used as a reference point when South Portlanders give directions.


The historical society sells Christmas ornaments featuring landmarks around the city, such as the Liberty Shipyard and Bug Light. In 2017, they came out with a Red’s Dairy Freeze ornament that had the phone “ringing off the hook.”

“It proved to be a huge seller for us,” DiPhilippo said. “There was a constant flow of people at the door saying, ‘where are the Red’s ornaments?'”

Red’s has a wealth of loyal customers, many of whom have been coming for generations. DiPhilippo, for instance, said she remembers going to Red’s as a kid and now goes with her own children.

“I grew up putting the spoons in the containers,” Josef said. “There’s a lot of customers who say, ‘I remember you when you were little.'”

There are customers who have been coming even longer than that.

“Red was a local milkman,” Gregoire said. “People will still come to Red’s and remember him delivering milk to their house.”

Gregoire and Josef are proud of the long-standing family business and are grateful for all of the support they have received over the years, and the hard work their grandfather and father have put in to keep it running.

“I think that it’s lasted this long with the support of the community and my dad’s passion and dedication,” Gregoire said. “Having this place be his father’s and then his; he truly enjoys it and I think that shows.”

Red’s continues to reel in customers 70 years after opening its doors. Ben McCanna / Portland Press Herald

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