In the area where the four-story South Portland Housing Authority building is today, there used to be two small buildings that housed a variety of businesses over the years. The history of these buildings dates back to the late 1960s.

Prior to 1965, Waterman Drive didn’t exist. The lettered streets, A, B, C and E, all ended at the waterline on the west side of Knightville. At the end of E Street, the city of South Portland operated a “burning dump” where trash would be burned and then pushed into the ocean. In 1964, the city embarked on the creation of what was then called the Knightville Bypass. Throughout 1965, construction of the bypass was undertaken, now being called Waterman Drive, named in honor of Albert Waterman, a longtime director of public works.

The section of Waterman Drive from the bridge to Market Street was new construction on filled land. The section from Market Street to Broadway had already existed (it had previously been called Commerce Street). The combined and completed Waterman Drive first opened to traffic on Sunday, Nov. 21, 1965.

When it opened, it created a new traffic pattern in Knightville, with traffic flowing one-way off of the bridge, via Waterman Drive to Broadway. Traffic returning to Portland would do so via Ocean Street.

With all of the incoming traffic from Portland flowing down Waterman Drive, it didn’t take long for entrepreneurs to see the potential. In 1966 alone, a coin-operated car wash and a Texaco gas station opened, and Wolfe Ford built its new showroom and service garage (the site is now home to Yankee Ford).

In 1969, Martin “Bud” and Bartley Costello, brothers who formed a partnership called Cosbro Associates, acted as developers and came forward with a plan to build out the lot on Waterman Drive between B and C streets. Cimino Construction was hired to construct two buildings.

Jordan’s Big Beef leased 90 Waterman Drive, a small A-frame building, and Dante’s, Inc. leased the building at 100 Waterman Drive.

Jordan’s Big Beef was one of two local retail stores (the other was on Route 1 in Falmouth) opened by the Jordan brothers, who also owned Jordan’s Ready-to-Eat Meats in Portland. The Jordan’s building was completed first – they received their occupancy permit in December, 1969. The drive-in restaurant featured roast beef sandwiches and hot dogs, but also offered ham and pastrami sandwiches, hamburgers, French fries, shakes, sodas and other treats.

Dante’s was a pizza and spaghetti restaurant. Their building at 100 Waterman Drive was completed in early 1970 and the occupancy permit was issued in February, 1970.

The two restaurants held a joint grand opening celebration on Feb. 4, 1970. In spite of their new facility and attractive signage, Dante’s was the first to go. The restaurant closed in December, 1970, after only 10 months in business. Jordan’s Big Beef did a little better, but they closed in the fall of 1972, less than three years after opening.

After Dante’s closed, the 100 Waterman Drive building had several different restaurants utilize the space over the following decades:

– Maria’s Restaurant operated from the site for four years from December, 1971, to December, 1975. Maria’s was reportedly founded by Larry Napolitano. He was joined in the business by his friend, Al Piscopo. Maria’s Restaurant specialized in Italian, American and seafood cuisine. Larry’s brother was Tony Napolitano, founder of Napoli’s Restaurant in 1960, which later became Maria’s Ristorante that still exists today in Portland.

– Frank Maffei operated Maffei’s Restaurant at 100 Waterman Drive from roughly 1977 to 1978. Maffei’s specialized in fine Italian cuisine.

– Pedro’s Fine Mexican Food opened in the space in March, 1979. This franchise restaurant was owned and operated by the Andrew and Myrna Ring family of Cumberland. They were in business for several years at the 100 Waterman Drive building, then moved the restaurant to the food court in the Maine Mall in 1984.

– After being vacant throughout 1985, 100 Waterman Drive became home to a Mister Bagel location, from January, 1986, through the early 1990s.

After Jordan’s Big Beef closed in 1972, the little A-frame building at 90 Waterman Drive also had several other tenants over the years:

– In October, 1976, Bill Kinsman opened a sandwich shop in the space. He had been operating his original pizza restaurant in Yarmouth since 1974, under the name Bill’s Pizza, however, Bob Bergeron owned the original Bill’s Pizza, which had been established in Old Orchard Beach in 1949. The name had been trademarked in 1964.

With the Yarmouth location far enough away, the two businesses had both operated as Bill’s Pizza, but with Kinsman opening a store in South Portland, across the bridge from one of Bergeron’s stores, Bergeron pressed the issue. Kinsman agreed to change the name of his restaurant, so the location in South Portland opened as Don’s and Bill’s Sandwich Shop, with Kinsman’s brother-in-law, Don Herron, managing the South Portland store. While they still sold pizza, they decided to specialize in sandwiches at this store, so as not to go into competition with Pizza by Angelone nearby.

– Around 1979, Vivian’s opened at 90 Waterman Drive. This was a second location of Vivian’s. The original Vivian’s Drive-In was located on Forest Avenue in Portland. Vivian’s made subs, sandwiches and pizza.

– By 1983, Sterling Insect and Lawn Control had taken over the space. They remained in business at that location through 1994, then moved to 904 Broadway where it remained for many years. It is now in operation in Gorham.

– In 1995, Port Harbor Marine began using the building and surrounding lot for boat display and sales.

– In early 2000, Beale Street Barbeque began an expansion of the A-frame building. It was completed and they received their certificate of occupancy in May of 2000. They remained at this location through 2007, then moved to 725 Broadway.

In December, 2006, the city of South Portland issued a demolition permit for 100 Waterman Drive. The permit for 90 Waterman Drive was delayed while Beale Street located a new facility. The demolition permit for that building was issued in January, 2008. With both buildings razed, the site was now ready for the construction of the four-story office building that is home to South Portland Housing Authority today.

Very few photographs exist today to document these two buildings and the restaurants and sandwich shops that occupied them. I hope that by publishing this column, we’ll reach someone who may have photos to share with the South Portland Historical Society.

South Portland Historical Society has many lectures, author talks and other programs planned through the winter months and into the spring. Historical society programs are free for current members, so if you are a South Portland resident and not already a member, we hope you’ll take this opportunity to start your membership, enjoy one or more of our programs, and know that your membership dues help support the historical society and its mission to preserve our local history.

A one-year family membership is only $25. Donations can be made through our Online Museum at https://sphistory.pastperfectonline.com, or if you’d prefer to donate by check, please make it payable to South Portland Historical Society and mail to us at 55 Bug Light Park, South Portland, ME 04106. Thank you. If you need to contact the society, we can be reached by email at sphistory04106@gmail.com or by phone at 207-767-7299.

Kathryn Onos DiPhilippo is executive director of the South Portland Historical Society. She can be reached at sphistory04106@gmail.com.

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