In 1910, two years after the publication of the internationally successful Anne of Green Gables, the publisher L.C. Page invited Maud to come for a visit to Boston. She was thrilled with the opportunity to meet Page himself and also to taste something of the high life of Boston literary society.

She was a guest of Page and his wife in their Brookline mansion and she was treated to dinners, luncheons, and outings. Her visit coincided with the twenty-fifth anniversary of the New England Women's Press Club. This large gathering, attended by more than three hundred, had Montgomery in its receiving line along with the American best-selling author and journalist Lilian Whiting. Montgomery confessed to her diary (SJ, II, 32) that she was bored by the event and worn out from standing in the receiving line for more than two hours while thanking women over and over for their kind words about Anne. The conference boasted letters of support from Thomas W. Higginson, famous editor (known nowadays as the man who discussed poetry with Emily Dickinson), and from popular poet Ella Wheeler Wilcox. Montgomery had an opportunity to meet Colonel Higginson at a dinner given by her famous fellow-PEIslander Basil King, respected intellectual and author. Of this event, Montgomery said, "The room swarmed with celebrities. One was Colonel Thomas Wentworth Higginson, a very old man, the sole survivor of the Longfellow-Whittier-Emerson set. I, myself seemed not altogether uncelebrated. When I came away Mrs. King said, 'You have been our "great gun" this evening' "(SJ, II, 33).

Montgomery collected postcards and souvenirs of the literary sites she visited, such as Hawthorne's homes, the Wayside and Old Manse; Louisa May Alcott's home, Orchard House; and the Old North Bridge, featured in Emerson's poem. Like most Canadians of her time, Montgomery knew a great deal of American history and may have shared many Prince Edward Islanders' and Maritimers' fascination with Boston. Like many Islanders, she had close relatives living and working in Boston. Later, Maud and Ewan would visit his sister in Braintree, Massachusetts, just outside Boston, and Boston became the place where she was to fight her legal battles against the L.C. Page and Company.