SOUTH PORTLAND — For those who don’t quite understand how beloved Red’s Dairy Freeze is by generations of South Portlanders, here’s the cherry atop the sundae: The city’s historical society has created a keepsake holiday ornament commemorating the cinder-block soft-serve stand.

In past years the historical society has chosen to honor venerable South Portland landmarks like the Portland Breakwater Lighthouse (known locally as Bug Light), Fisherman’s Point with its historic fishing shacks overlooking Willard Beach, and the city’s World War II-era shipyards.

Red’s service to the community, though not quite so profound, is appreciated on a more emotional level. Founded in 1952 on Cottage Road at the base of Meetinghouse Hill, it’s the place where parents take children for their first cone, where Little League and soccer teams celebrate the big win, and where summer nights are that much sweeter. It doubles as a seasonal clock, watched intently by residents hoping for an early spring and a later summer. When Red’s opens each spring, news spreads like wildfire, with its Facebook page getting hundreds of likes in a couple of hours.

“When it’s March and you see Red’s open, you know it’s spring. And in October, you almost dread knowing it’s going to close, and you want to get there just one last time before winter,” said Jim Minott, 67, former principal of the nearby Frank I. Brown Elementary School.

The historical society’s board picked Red’s after trying to think of a place that was well-known and beloved enough for people to want to spend $20 on an ornament depicting it. The society sells the brass-plated metal ornaments each year as a fundraiser at its museum in Bug Light Park and at local stores.

“Red’s is just so popular that it made sense for us. When people give directions (in South Portland) they use Red’s as a landmark,” said Kathryn Onos DiPhilippo, executive director of the South Portland Historical Society. “So many generations have gone there. So many people wanted to help when they had the fire (in 2010).”


South Portland Historical Society’s Christmas ornament commemorating Red’s Dairy Freeze on Cottage Road, as shown on the society’s Facebook page.

Chris Bolling, whose family has owned Red’s since its inception, said he was “totally surprised and very honored” when society board members asked if he’d agree to have his business on an ornament.

“We’re always surprised by the reaction we get from the community. We try to help the community and be good neighbors, but you don’t expect something like this. It’s not like we’re the only business in town people like,” said Bolling, 62.

The ornament of Red’s is oval-shaped and about 3 inches wide. The name “Red’s Dairy Freeze” is engraved above an image of Red’s, with its barn-style red roof and a giant ice cream cone sign above the service window. The image also shows some parked bikes, people in line and kids in team uniforms. The ornament was created by a custom-ornament company in South Carolina, using a photo of Red’s.

Red’s was opened at the corner of Cottage Road and Walnut Street 65 years ago by Leonard “Red” Bolling, a delivery driver for Hood dairy products who lived nearby on Hillside Avenue. It was originally called Tastee Freeze but renamed Red’s Dairy Freeze around 1965. It’s located in a mostly residential area, just a short walk from Mill Creek Park and area stores, and across the street from the South Portland Public Library, the Brown School and Mahoney Middle School. So there’s a ready supply of youngsters walking past it every day. Not to mention grown-ups.

Minott strolled across the street for a treat so often while he was principal at Brown School that Bolling would see him coming and scoop up his favorite, The Boston, a Red’s specialty featuring a fudge sundae floating atop a chocolate shake.

The scene at Red’s Dairy Freeze in South Portland on an August night in 2015

When an electrical fire heavily damaged Red’s building in 2010, students from local schools held bake sales and other fundraisers and donated toward the rebuilding effort. The building was torn down but rebuilt to look the same.


When the soft-serve stand reopened in March 2011, several dozen people gathered in the cold awaiting their first Red’s treat in 10 months. First in line were firefighters who had responded when Red’s was burning. At least one father in the crowd that day had taken his son out of middle school to be at the reopening.

Linda Cohen, a South Portland city councilor, began going to Red’s in the 1970s, when Red himself was behind the order window. She thinks the fact that it’s seasonal, that it takes breaks now and then, makes it stand out in a hectic world. It usually closes in mid-October and opens in March.

“That makes it even more special. We’re sad when it closes and look forward so much to its opening,” said Cohen.

When the historical society’s board members first considered Red’s for an ornament, they “scratched their heads” for a moment, said Chuck Igo, a board member who lives up the hill from Red’s. The other ornaments commissioned by the society had featured more traditional historic landmarks. But it didn’t take long for everyone to realize selling images of Red’s to local folks was a no-brainer.

“Three going on four generations of people have gone there. When it opens each year we all have a little more hope that spring is actually coming,” said Igo, a morning host on radio station Rewind 100.9. “It’s really an icon and means a lot, emotionally, to people around here.”

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