Now a three-family apartment building, the home at 88 Pillsbury St. in South Portland has an interesting past with ties to a building on Broadway where the Sea Dog Brewing Company restaurant and bowling alley now exists.

The Meaher family once owned and lived in the large home at 88 Pillsbury St. The home was located on one very large lot of land that extended all the way to Cottage Road and encompassed the area that now has the Portland Players theater on it. In 1922, John Cragg purchased the large home and lot and proceeded to subdivide the property, creating Craggmere Avenue and selling off the smaller lots for residential home building.

The existing large home on Pillsbury, however, became the centerpiece of his wife Isabel and their daughter Beatrice’s summertime activities for several years.

Jean “Isabel” Baker was born in New York and was a teacher in Concord, New Hampshire, when she met John Cragg who was working as a book binder, also in Concord. They married in 1894 when she was 22 years old. They moved to Portland where Isabel gave birth to their first and only child, Beatrice Baker Cragg, in 1895.

While John was busy working his way up in the printing/bookbinding business (he would eventually own the Seavey Company, a printing company in Portland), Isabel was busy raising their daughter.

By around 1916, Isabel and Beatrice were living in Boston during the school year; while Beatrice was studying piano pedagogy at a music school, Isabel opened the Isabel Baker Cragg School of Dance at 200 Huntington Ave. Isabel’s school of dance was located just one block away from the New England Conservatory of Music, and also very close to the Berklee College of Music and Northeastern University.

Beatrice finished her studies and, by the summer of 1918, she and Isabel had moved back to Portland. In the fall of that same year, they opened the Chateau at 609 Congress St. (the large building at Congress Square where the State Theater is also located). The Chateau was a dance hall that they would rent out for private dances and parties. Isabel also opened her Isabel Baker Cragg School of Dancing at the Chateau, and daughter Beatrice offered piano lessons there, as well, taking on students who were 5 to 16 years old.

In 1922, Isabel and Beatrice converted the former Meaher residence at 88 Pillsbury St. into a tea room and dance hall known as the Jack O’Lantern Casino. An article in the Portland Sunday Telegram on May 22, 1922, provides some details of the new attraction: “Next Saturday evening will witness the opening of Portland’s newest dance casino, the Jack O’Lantern, ‘atop Meeting House hill, South Portland. Mrs. Isabel Baker Cragg, who has successfully run the Chateau has bought the big house situated next to the schoolhouse [the Willard School] on Pillsbury Street and has converted the big barn into a splendid dance hall with new hard wood floors. The house itself will be used as a tea room, catering to the dancers and automobile travelers. Whitman’s Bowdoin College Orchestra has been engaged for the entire Summer to furnish music, and this popular organization will do their best to please lovers of dancing.”

The Jack O’Lantern Casino on Pillsbury Street was in operation during the summers for three years. It was a good arrangement since dance and piano lessons would typically be taking place from the fall through spring. After they would close the casino in the fall, Isabel and Beatrice would start back up with the dance and piano lessons at the Chateau in Portland.

In 1925, Isabel and Beatrice moved the Jack O’Lantern operation to a new location at 717-731 Broadway. According to an article in the Portland Sunday Telegram on April 5, 1925, “The opening of the new Jack O’Lantern Casino, which is ideally located…overlooking the water, will be one of the early spring events. Those who have enjoyed the dancing parties at the old Jack O’Lantern for the past three years, will be delighted with the new one, which is more modern and attractive in every way. The large piazza which extends around the casino will be delightfully cool and splendidly adapted for afternoon bridge parties, several of which are already booked…The lighting and decorations are to be decidedly unique. In the center will be the fascinating crystal ball. The casino is to be under the personal direction of Mrs. Isabel Baker Cragg, who has been in charge of the successful community dances at Frye Hall the past five years, and who has a well-established school of music and dancing at the Chateau.”

In May, 1925, Isabel Baker Cragg had 75 children take part in a dance recital. The newspaper reported, “Always striving to have each festival unique and different, Mrs. Cragg has planned this dance revue in the form of a cabaret and it will be given at the spacious new Jack O’Lantern casino on Summer Street [Broadway], South Portland. It will be the most elaborate affair of its kind ever staged here.”

In May, 1926, the Craggs lined up a celebrity to draw the crowds. “The Jack O’Lantern is very fortunate in having Miss [Connie] DeAyer, a motion picture star who not only makes a personal appearance but produces on the ballroom floor the same series of Charleston dances that has made her one of the screen’s greatest stars. Miss DeAyer first does the Charleston the way it is done on the lot before the camera; second, the Charleston as she does it herself at a party; and third the Charleston triple time, with all the latest steps and variations. She has promised Miss Cragg, manager of the Jack O’Lantern, that she will dance with several Portland young men in order to compare their steps with the royalty of Europe, with whom she has danced, including the King of Spain.”

By the mid-1930s and through the 1940s, Isabel and Beatrice operated their dance and music studio at 10 Congress Square in Portland under the name “The Modern School of Dance and Music” and later changed the name to “The Model School of the Dance.” Around 1944, Isabel retired and left Beatrice to run both the dance/music studio as well as the Jack O’Lantern dance hall on Broadway, which Beatrice renamed “The Jack” and continued operating until roughly 1949. By 1950, the dance hall on Broadway had been turned into a roller-skating rink.

After Isabel died in 1951, Beatrice was left as owner of the Seavey Company, the printing and bookbinding company in Portland that her dad had run. With both of her parents now gone, Beatrice and her husband James Hervey focused their attention on running the printing company. James Hervey died in 1968 and Beatrice Baker Cragg Hervey died in 1974. They are buried next to Beatrice’s parents at Evergreen Cemetery in Portland.

If you have photos, artifacts or information to share related to South Portland’s past, we would love to hear from you. South Portland Historical Society can be reached at 207-767-7299, by email at sphistory04106@gmail.com, or by mail at 55 Bug Light Park, South Portland, ME 04106.

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

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