South Portland Historical Society will hold a lecture at the South Portland Community Center on Wed, Nov. 29, at 6:30 p.m. Larry Legere, a retired captain for Casco Bay Lines, and now president of the board of the historical society, will give an illustrated lecture about the history of the many passenger steamboats that once carried passengers around our harbor. The lecture is free for current members of the South Portland Historical Society; non-members can attend with a $20 donation.

The steamer Maquoit heading back to its wharf in Portland. Edward Legere went to work aboard the Maquoit in 1943, when he was 15 years old. South Portland Historical Society photo

Casco Bay Lines, the passenger service to the islands of Casco Bay, is the oldest continuous year-round ferry service in the United States. Beginning in 1871 as the Casco Bay Steamboat Company, its history is long and rich.

My family’s relationship with the vessels, the islands, and the residents of Casco Bay is long and rich as well, spanning 74 years through three generations. It began in the early 1940s when a family friend told my grandfather that the steamboats were a healthy summer job where his boys could keep in shape for their scholastic sports.

In 1943, my dad Edward Legere, age 15, went to work aboard the Maquoit on the Bailey-Orrs Island run. This was a plum assignment as he served with Capt. Earl Stockbridge, senior captain of the fleet.

Piloting the coal-fired steamers through Casco Bay during World War II was not an easy task. Anti-submarine nets and mine fields were positioned to protect the North Atlantic Fleet anchored in Hussey Sound between Falmouth and Long Island. The routes to avoid them made the trip longer and a bit more tricky.

Edward Legere served as mate on the steamer Aucocisco. South Portland Historical Society photo

Three years later, after graduating from South Portland High School, Edward enlisted in the United States Marine Corps for a year, returning for the 1947 season. He was promoted to Mate on the “queen of the fleet,” the Aucocisco, and studied and sat for his pilot and small boat captain’s license. During those years, he also kept a small collection of photos of his time afloat. More about those a bit later in the story.


My own experience with Casco Bay Lines began about a decade later. Edward had gone back to work on the boats as a fill-in captain on the weekends for golfing money. I began riding with him as a very young lad and developed a love for Casco Bay and the boats that plied its waters. I remember vividly the last of the wooden-hulled vessels including the last coal-fired steamboat, the Sabino.

Fast-forward a dozen years and it was my turn to go to work on the boats. By 1977, I had acquired my captain’s license at age 21 and was living my boyhood dream. I had always been interested in the history of the glamorous age of steamers, the bay they traveled through and the people they carried, and I was able to speak with many of the older generation who were there during part of that era.

The Forest City, the Emita, and the Mary W. Libby at Custom House Wharf in Portland in 1894. The Mary W. Libby (in the foreground) was one of many boats used as the Cape Elizabeth Ferry over the years, carrying passengers between Ferry Village in South Portland and the Portland waterfront. South Portland Historical Society photo

The collection of steamboat photos from my dad began to grow as I began to reach out to many other sources to acquire more and create a larger database. As my career at Casco Bay Lines continued, I became the “Unofficial Historian” and was tasked with much of the outreach to schools, historical societies, and other organizations.

My collection grew to several hundred items and as other collectors learned of it, the demand for copies and viewing of it also grew. In the early 2000s, I decided the collection needed to be protected and more available to interested historians and so I donated it to the local Portland Harbor Museum. Sadly, the museum folded and the collection was absorbed by the Maine Maritime Museum and now resides in Bath.

Before the photos went to Bath, I had 48 of the most interesting and eclectic prints transferred to old-fashioned slides and took these on the road to present to interested organizations. Many of the photos were used on the murals displayed in the Casco Bay Lines passenger terminal, further cementing their historical legacy.

The lecture on Wednesday, Nov. 29, consists of my stories and interpretation of the vessels of Casco Bay and is not a comprehensive history of Casco Bay Lines (for a more comprehensive history, see, or William Frappier’s book, “Steamboat Yesterday.”


After 20 years, people are still showing an interest in my photos and stories and I am delighted to present this program on Nov. 29.

Sunday Chat Series

On Sunday, Nov. 26, author Paul Ledman will be at the historical society’s museum at Bug Light Park from 11 a.m. to 1 p.m. Paul is the author of the best-selling book, “Walking Through History: Portland, Maine on Foot.” His newest book, “Portland, Maine: Connections Across Time,” is an intriguing work that connects Portland history to contemporary global events.

The book is packed with maps and photographs that help the reader understand the many connections between historic Portland and national and global trends. Paul will be available to chat with visitors and sign books.

All of Paul’s books, including his book covering South Portland/Cape Elizabeth during the Civil War, are available for purchase in the museum gift shop, with net proceeds supporting the historical society and its museum.

Society ornaments available

The South Portland Historical Society’s 2023 fundraiser ornament features the historic Mahoney school building. Ornaments are on sale at the historical society’s museum in Bug Light Park (open Saturdays and Sundays). South Portland Historical Society photo

The South Portland Historical Society’s fundraiser ornament for 2023, featuring the Mahoney school building, is available. All 10 of the society’s landmark-series ornaments can be purchased at the museum at Bug Light Park, open on Saturdays and Sundays from 10 a.m. to 4 p.m.

A limited supply of ornaments is also available for sale daily at our two retail partners – Drillen Hardware and Broadway Variety. The stores generously sell the ornaments and collect the proceeds for us; the ornaments are $20 each and can be purchased with either cash or check at those locations. If you want to use a credit card, or if you want to purchase four or more of any one ornament, we recommend that you plan to purchase them at the museum. If you would like to purchase an ornament to be shipped, please call the society at 207-767-7299 or contact us by email at

Larry Legere is president of the board of directors of the South Portland Historical Society.

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