The Cookie Jar Pastry Shop, established in 1956, has been owned and operated by the Piscopo family since the early 1970s. This small, much-beloved bakery is a destination for customers throughout Greater Portland and beyond. Contributed / South Portland Historical Society

The Cookie Jar ornaments are now available at South Portland Historical Society, Drillen Hardware, Shoppers Hardware, Broadway Variety, and the Cookie Jar. Contributed / South Portland Historical Society

South Portland Historical Society is excited to announce its 2024 landmark ornament – the Cookie Jar. With thanks to Tom and Donna Piscopo, this fundraiser ornament, 11th in a series, commemorates the bakery that has been providing tasty treats to people throughout Greater Portland for nearly seven decades.

The history of the Cookie Jar bakery is an interesting one. The building was first constructed in 1950 as a hamburger joint known as Carl’s Restaurant. It was owned by Carl and Roberta Sheaff, longtime South Portland residents. Many may remember them as the owners/operators of Carl’s Catering in South Portland for 25 years.

In June, 1950, Sheaff leased the vacant lot of land at 554 Shore Road in Cape Elizabeth from the Taylor-Dow Co. Taylor-Dow was headed up by Stewart Taylor, who was also the president and general manager of Hannaford Bros. The lease clearly stated that Sheaff was about to erect a building on the site, and it further stated that “it is understood that no intoxicating liquor or beer are to be served on this property or on any other establishments that will be detrimental to the community.”

The Cookie Jar building was first constructed in 1950 as a hamburger joint, known as Carl’s Restaurant. Contributed / Donna Piscopo

Although Carl Sheaff’s name was on the lease, it was his wife, Roberta, who ran Carl’s Restaurant while he was in the U.S. Navy. He had enlisted in 1936 and served throughout WWII and during the Korean War. He was on active duty when they had the building constructed in 1950 and opened the restaurant. In a social news column on Christmas Day in 1950, Carl was noted as being home on leave from an aircraft carrier, visiting with his wife in their home at 108 Hillside Ave. in South Portland. Roberta ran Carl’s Restaurant on her own until Carl was finally discharged from the service in October 1951, and came home to run it with her.

While operating the restaurant, they began offering catering services. In 1956, they decided to focus on their catering business, Carl’s Catering Service, which they were able to do out of their home. They sublet the building to the Paulson sisters – Lila Gaudet, Agnes Turcotte and Ruth Dunn Williams, all daughters of Knute and Carrie Paulson – who had decided to open a bakery together. Turcotte’s husband, Paul, had served in the Navy along with Carl Sheaff (they served on the USS Hamilton together). The sisters opened the Cookie Jar on Oct. 8, 1956, and a landmark business was born. They leased the building at first, then Gaudet and her husband, James, purchased the property from Taylor-Dow in 1961.

An advertisement for Carl’s Restaurant that appeared in the Portland Evening Express in October 1951. Contributed / South Portland Historical Society

Around 1960, two of the Paulson sisters, Turcotte and Dunn Williams, opened a second location of Cookie Jar at 286 Ocean House Road (that location was short-lived – gone from records a year later). Gaudet remained at the original bakery on Shore Road and Jim Collett came in to work with her (Collett was another WWII veteran who had served in the Navy; he and his wife, Lillian, lived at 21 Barstow St. on Meeting House Hill in South Portland). Around 1964, Gaudet finally left the business and Collett continued to run it on his own.

When Collett became ill in November of 1970, he offered to sell the business to two key employees, Ada Tordoff and Grace Piscopo, both of whom were his bakers. Tordoff was not interested, but Piscopo was. She had been working there for many years already; she had seen a “help wanted” ad in the window, walked in and was hired. She had learned the baking trade from Collett. Piscopo and her husband, Frank “Ikey” Piscopo, lived at 26 Bonnybriar Road in South Portland; Ikey worked at Portland Stove Foundry. After Collett died in the summer of 1971, Grace and Ikey Piscopo bought the bakery from Collett’s widow. Ikey still worked at the foundry at that time, but he soon left and joined Grace in the business. They leased the building at first, but purchased the property from Gaudet in 1973.

This advertisement in the Portland Sunday Telegram on Oct. 7, 1956, announced the opening of the Cookie Jar the next day. Contributed / South Portland Historical Society

Around 1976-1977, the Piscopos opened a second retail store in South Portland. The Cookie Jar Pastry Shop at 568 Main St. was a retail outlet only, supplied by the bakery on Shore Road. When they determined that the results didn’t warrant the effort of operating another location, they closed that store. Their son, Tom, and his wife, Donna, joined them in the business and, in 1981, they bought the bakery. As most locals know, the Cookie Jar has remained a popular bakery over the years, doing a brisk business each day. The one major setback that they endured was when a huge storm in late October 2006 blew the roof off the building, flooding the bakery. The Piscopos and more than a dozen employees were inside at the time; they had to evacuate and about $5,000 worth of bakery products, and another $5,000 in raw materials, were ruined by the rain that poured in.

It was a devastating loss and the bakery was closed for several years. In March 2010, building renovations began and the bakery reopened on May 27, 2010, to the delight of the local community. More than 900 people showed up on reopening day, so happy to have their beloved Cookie Jar back in business.

Today, Tom and Donna Piscopo are blessed to have their two sons, Thomas and Nicholas, along with Thomas’ wife, Olivia, all actively working in the business with them. Their grandson, Noah, can also be seen around the bakery at times, undoubtedly in training to be the next generation of Piscopo bakers.

Cookie Jar ornaments

The historical society’s fundraiser ornaments have become a fun yearly tradition. We have just released our 2024 ornament featuring the landmark business, Cookie Jar Pastry Shop. The ornaments are $20 and on sale at the society’s museum gift shop at Bug Light Park where you can pay by cash, check or credit card. All 10 of our previous ornaments are available at the museum, as well. Prior year ornament designs include Bug Light, Fishermen’s Point, Liberty shipyards, Red’s Dairy Freeze, Willard Square, Spring Point/Fort Gorges, Cape Elizabeth train depot, Thornton Heights fire station, and the Mahoney and Memorial schools. There are also several generous retailers who have agreed to offer the ornaments for sale, with all proceeds still going to the historical society. Please plan to pay by cash or check at the outside retail locations: Drillen Hardware on Cottage Road, Shoppers Hardware in Mill Creek, Broadway Variety on Broadway, or at the Cookie Jar. For more information, call 207-767-7299 or email sphistory04106@gmail.com.