The first annual meeting of the Massachusetts Society of Mayflower Descendants was held on November 21, 1896, at the Tuileries in Boston. Such illustrious people as Governor Roger Wolcott, Mayor Josiah Quincy (III) of Boston, Charles Eliot of Harvard, and historian Justin Winsor were invited. None came. Among those who did attend that first dinner were Winslow Warren, Collector of the Port of Boston; Arthur Lord, President of the Pilgrim Society; Henry E. Cooper, Minister of Foreign affairs for Hawaii; and the Marquis Paul de Rousiers. Out of a total membership of about one hundred at that time, fifty-five members joined with forty guests to enjoy dinner, music and various addresses.

Typical of the large dinner meetings held in the early years of the society is the report given in the Boston Evening Transcript of November 22, 1900, which described the walls of the State Suite of the Vendome Hotel decorated with the Flags of England, Holland, and the United States. Beside each plate on the tables was a tiny dish with four grains of corn "to emphasize the contrast between the want of the Pilgrim fathers and the plenty in which their sons and daughters live." Menu cards were illustrated with pictures and the text of the Compact, and at the lower end of the hall, partially hidden by screens, was a quintet from the Boston Symphony Orchestra. The menu for the 1905 celebration of the signing of the Compact included Cape oysters, bisque of lobster aux soufflés, consomme printaniere, fried smelts with tartar sauce, pommes Italienne, roast Philadelphia capon with cranberry sauce, filet of beef with marron sauce, hubbard squash, string beans, crème de menthe punch, sweetbreads en croustades, pear fritters glace au cognac, harlequin ice cream, assorted cake, fruit, cheese, and coffee. Speakers at the annual dinners were usually trotted out in droves to make "short" remarks, rather than featuring one speaker on one subject as is common now. Subjects centered on the bravery and purity of the Pilgrims or the responsibilities of their descendants to carry on the morality and character of their forefathers in a changing world, such as the following by Winslow Warren:

[The Pilgrims'] love of liberty and of law and order, recognizing the responsibility to a higher power above, has been inherited by their descendants. It is our duty to see that Massachusetts is true to that spirit ... What the country needs is a sense of its history. There are no heroes to the unheroic. The Mayflower crossed not only the ocean, but the centuries.

Speakers were usually prominent people in local or state arenas of politics, history, education, or culture including Hosea M. Knowlton, Attorney General of Massachusetts, Prof. Albert Bushnell Hart of Harvard, Elmer Capen of Tufts, incorporator Charles Francis Adams, and Katharine Lee Bates of Wellesley College.

There were also occasional meetings with a speaker reading a prepared paper followed by a reception. These were usually attended by one hundred to two hundred people and subjects included "The Relation of the Pilgrims to Their Times," "The Pilgrim and the Puritan," "Colonial and Revolutionary Society Life," "The Cheerful Side of the Pilgrim Character," "The Pilgrims, the Foundation Builders of the Republic," "Some New England Women of Colonial Days," and "The Myth of Mary Chilton."

Excursions outside of Boston drew from thirty to seventy-five people who would take a special car on the train from Boston to the nearest station and travel by boat, electric car, or carriage from there. In May of 1897 members went to Plymouth where barges carried them to the Pilgrim monument, Plymouth Rock, Burial Hill, and so forth. Dinner was served at the Samoset House, and Plymouth historian, William T. Davis, spoke on "Pilgrim Anniversaries of Former Days." In June of 1899 they journeyed to Squantum Inn, Quincy (fare from Boston by steamer ten cents, by train and electric car, 11 cents), where they had a shore dinner. June 1900 saw members traveling to Duxbury to visit Powder Point, Duxbury Beach, the Standish Monument, etc. In June 1903 they gathered at Salem to view the only extant Mayflower gravestone (that of Richard More), and a September 1905 pilgrimage led to the Society's small lot, referred to as the "Bradford Meerstead," and other sights in Kingston.

Celebrating Forefathers Day (December 21 st, the day the Mayflower landed in Plymouth - as opposed to November 21 st when it reached Provincetown and the Compact was signed) was George Ernest Bowman's idea. One of the first recorded celebrations of the Pilgrims by their descendants was on Forefathers Day in 1799. In February of 1899, at a special meeting, Bowman read an account of the "Feast of the Sons of the Pilgrims" on that occasion one hundred years before. The idea was well-received and in December of 1900 a service was held at the Central Church in Boston complete with an original song, The Breaking Waves Dash'd High. Kings Chapel, Trinity Church, First Church, Arlington Street Church and Mt. Vernon Church each held services in the next six years. The 1905 address by the Reverend Albert Parker Fitch at Mount Vernon Church was printed in The Mayflower Descendant:

The consciousness of a great past is a precious inheritance and a powerful incentive for a nation ... Let us meditate upon this thought that the true descent is the unbroken transmission of spirit, vision and ideal ... Am I true to my inheritance ... I have received these national ideals, these public gifts of the spirit of popular government, universal education, religious liberty, noble responsibility for the best interests of man kind ... Success is measured, not by what we achieve for ourselves, but by what we achieve for others ...These are the things and the only things, members of the Society of Mayflower Descendants, which give you the right to the high ancestry you claim.

After the Society's move to Mt. Vernon Street in 1906, more informal monthly "at-home" days at the Society's rooms, featuring tea and light refreshments, were begun.

In addition to social events, the society began publication in 1899 of the quarterly magazine The Mayflower Descendant, edited by George Ernest Bowman. Recognized as the most authoritative publication on Mayflower genealogy, the magazine gave the society a reputation for genealogical accuracy and integrity. Bowman's vision was to present genealogies of the Mayflower passengers that exhausted every available source of information. A smaller section of the magazine called Pilgrim Notes and Queries was briefly published independently. Books of transcriptions of town vital records for Brewster, Halifax, and Truro were also produced, as were epitaphs from graveyards in Kingston, Yarmouth, and Yarmouthport, and a reprint of Governor Bradford's letterbook.

The Society's first offices were rented rooms at 623 Tremont Building. They later moved into 53 Mt. Vernon Street, where they stayed for twenty-three years until the building on 9 Walnut Street was purchased. Bowman began an ambitious acquisitions program beginning with the item that is still the Society's most valuable possession. The Brewster Book, a wast or blank book containing records, letters, lists, commissions, and children's drawings, had apparently been part of Elder William Brewster's estate and the main entries had been kept by his son Jonathan Brewster. It was donated to the Society by Cordilla W. Fitch of Morrisville, Vermont, who had inherited it. Mr. Fitch also donated the second most important manuscript in the Society's collection, the diary of Jabez Fitch Jr., kept between 1749 and 1812.

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