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This collection is made up of the papers of five generations of the Dwight, Willard, Alden, Allen, and Freeman families of the East Coast and (later) U.S. Midwest, between 1752 and 1937. Around 3/4 of the collection is incoming and outgoing correspondence of family members, friends, and colleagues. The primary persons represented are Lydia Dwight of Massachusetts and her husband John Willard, who served in the French and Indian War; Connecticut mother Abigail Willard along with her husband Samuel Alden, who ran an apothecary in Hanover, New Jersey; Allen Female Seminary School alumna and teacher Sarah J. Allen; American Civil War surgeon Otis Russell Freeman; Presbyterian minister and temperance advocate Rev. Samuel Alden Freeman; and prominent public librarian Marilla Waite Freeman. The papers also include diaries and journals, writings, school certificates, military and ecclesiastical documents, photographs, newspaper clippings, advertisements, business and name cards, invitations to events, and brochures for plays and other performances.

The collection is arranged first by family grouping, then by material type. These series roughly reflect the arrangement of the collection when it arrived at the William L. Clements Library.

The Dwight-Willard-Alden Family Papers are comprised of around 250 items, dating between 1752 and 1884. One fifth or so of this grouping is predominantly correspondence between Lydia Dwight/Lydia Dwight Willard, her father, stepmother, siblings, husband, and sons, 1752-1791. These intermarried families were based largely in Sheffield and Stockbridge, Massachusetts. The letters include discussions about mending and cleaning clothing; feelings about their father/husband gone to serve in the French and Indian War; putting up a monument to replace faltering graves; the return of Elijah and Col. Williams from the field on account of sickness; coming and going of soldiers; moral and practical advice; teaching and boarding young students during the war; settling into (“no longer free”) married life; the death of Bathsheba Dwight; the meeting of local men in private homes and the training of minute men in Stockbridge; the prolonged case of smallpox experienced by Lydia’s son in 1785; and news of John Willard, Jr.’s admission to Harvard.

The remaining four fifths of this grouping are largely incoming correspondence of Abigail Willard Alden (1771-1832) and her daughter Abigail Alden (1809-1854). Their correspondents were located in Stafford, Connecticut; Hanover and Lancaster, New Hampshire; Lunenburg, Vermont; and elsewhere. They begin with letters from siblings and parents to the newly married Abigail Willard Alden (ca. 1800); Samuel Alden travel letters to New York City; and news of a Stafford doctor named Chandler who had promised marriage to a woman and then fleeced her for $500 before fleeing to parts unknown. A group of letters regard pharmacy matters, the burning of Samuel Willard’s drugstore (January-April 1802), and the state of Anti-Federalists and Federalists in Stafford (1802). A large portion the letters include content on sickness and health, with varying degrees of detail, including several family members sick and dying from measles in 1803. Other topics include Hanover, New Hampshire, gossip on local premarital sex; a debate on whether or not to hire a black female domestic laborer; comments on a local suicide attempt; a young woman deliberating on objections to women spending time reading novels (April 10, 1806); and treatment by a quack doctor. These papers also include two diaries, poetry and essays, two silhouettes, genealogical manuscripts, and miscellaneous printed items.

The Allen Family Papers are largely incoming letters to Sarah Jane Allen prior to her marriage to Samuel A. Freeman (around 300 items), and from her father-in-law Otis Russell Freeman (around 60 items) between 1860 and 1865. An abundance of the letters were written to Sarah while she attended the Allen Female Seminary in Rochester, New York, and afterward when she lived at Honeoye Falls, New York. They include letters from her parents, cousins, friends, and siblings. A sampling suggests that the bulk are letters by young women attempting to eke out a life for themselves through seminary education, teaching, and domestic labor. Among much else, they include content on Elmira Female Seminary, New York state travel, and female friendship and support.

The Otis Russell Freeman letters date between 1862 and 1865, while he served as a surgeon in the 10th and 14th Regiment, New Jersey Volunteers. He wrote about the everyday camp life with a focus on the health and sickness of the soldiers. His letters include content on the defenses of Washington, D.C., fighting at Cold Harbor and outside Richmond, Virginia, the surrender of Robert E. Lee, the assassination of President Abraham Lincoln, and Lincoln's body lying in state at Jersey City. Two carte-de-visite photographs of Otis Freeman are present.

A diary kept by Sarah J. Allen began on the day of her marriage, September 26, 1865, documents her honeymoon to Niagara Falls. It ends in November 1865. The remainder of the volume is filled with recipes for baked goods, pickles, and other foods. The printed items include ephemera from Sarah Jane Allen’s tenure at Elmira Female College five issues of the Callisophia Society’s newspaper The Callisophia (vol. 1, nos. 1, 3-6; March/April 1860-January/February 1861), as well as a Catalogue of Books in Callisophia Library, December 1862.

The Samuel Alden Freeman Family Papers include approximately 300 largely incoming letters to Presbyterian minister S. A. Freeman, plus printed materials, ephemera, photographs, and bound volumes, dating in the 1810s and from the 1860s to 1880s. Correspondence of his second wife Olive dates from the 1810s in central New York. The collection includes letters to S. A. Freeman from his first wife Sarah, daughter Abigail Alden Freeman (1873-1925), and Sara Harriet Freeman (1879-1946). These materials include courtship correspondence of Sarah Jane Allen and S. A. Freeman. A considerable portion relates to Presbyterianism and at least one temperance society pledge sheet is present. Approximately 50 photographs, about half of them identified, are largely of Samuel A. Freeman and the Freeman daughters Marilla and Abigail. Among the printed ephemeral items are advertisements for programming at Corinthian Hall (probably Rochester, New York), items related to a Sunday School Association (including a printed broadside catalog of books at a N.J. Sunday School), and pamphlets on Presbyterianism. A medicinal recipe book from the mid-19th century and a commonplace book of poetry are examples of the S. A. Freeman family bound volumes.

The collection concludes with letters, photographs, ephemera, and printed items comprising the Marilla Waite Freeman Papers. Around 600 letters are largely incoming to public librarian M. W. Freeman from female educators and librarians. They discussed their profession, books, reading, and intellectual topics. A small clutch of letters, about three dozen manuscript and typed poems, and a dozen or more newspaper clippings, 1900s-1910s, comprise poet Floyd Dell’s contributions to the collection. Marilla also corresponded with poets and writers Margaret Todd Ritter, Robert Frost and Mrs. Frost, and Marie Bullock about public and private recitations and lectures. Examples of subjects covered by the printed materials include orations, educational/school/college items, library-related items, newspapers and clippings, fliers, women's clubs, New York City theater, the American Library Association, Poetry Society of America, poems by various authors, such as Ina Robert and John Belknap, visiting and business cards, and travel.

The collection focuses primarily on John Tailyour, a Scottish merchant who traveled to North America and Jamaica in the 1770s and 1780s to conduct business, before finally returning to his home in Scotland in 1792. His correspondence is heavily business related, centering especially on his trading of slaves, foodstuffs, and sundry goods. It also chronicles the current events in both Jamaica and the Empire. Many of Tailyour's correspondents debate the meaning and merit of the cessation of the slave trade in the late 18th century, as well as the military events of the American and Haitian revolutions, and of the Maroon rebellion of 1795. The papers also include letters between John and his family in Scotland regarding John's mixed-race Jamaican children. He sent three of his children to Britain to be educated, which caused much family concern. Tailyour's account books and financial papers relate both to his Jamaican estate and business, and to his Scottish estate, from which he received added income from rents. The accounts for this estate continue for several decades after Tailyour’s death in 1815. A number of disparate and miscellaneous letters, war records, photographs, and realia that belonged to various members of the extended Tailyour family date mainly from the late-nineteenth and early-twentieth centuries.

The collection has three substantial parts. The most comprehensive and cohesive section is the one concerning John Tailyour, until his death in 1815. The second part contains business papers and accounts related to the Tailyour estate. The third part is the least integrated, and consists of a variety of family papers, photographs, military memorabilia, and other miscellanea.

The Tailyour papers date from 1743 to 2003, with the majority of the collection concentrating in the period from 1780 to 1840. Within these bulk dates, are the two largest portions of the collection: the correspondence and accounts of John Tailyour until his death in 1815, and the account records of the Tailyour estate after 1815.

Seven boxes contain John Tailyour's personal and business correspondence of 3757 letters. The letters focus on Tailyour's mercantile activities in the Atlantic market, especially on the slave trade, its profitability, and the threat posed by abolitionists. Tailyour's correspondence also chronicles personal and family matters, including the education and provision for his mixed-race children from Jamaica. In addition, the collection contains four of Tailyour's letter books of 1116 copies of retained letters that cover the period from 1780 to 1810, with the exception of the years 1786-7 and 1793-1803. In these letters, Tailyour's focus is business, particularly as it relates to the slave trade, but he also includes personal messages to his friends and family.

Tailyour's business papers contain 32 loose account records, as well as five account books documenting the years between 1789-90 and 1798-1816. These primarily concern his Kingston and Scottish estates, including the expense accounts and balance sheets for each, as well as the finances of his merchant activities during the period. Finally, 38 documents of probate records for John Tailyour mainly relate to his landed estate.

The latter portion of collection within these bulk years (1815-1840) also contains correspondence and accounts, although the 228 letters are almost entirely concerned with business accounts. These focus on Tailyour's estate after his death, with John's brother Robert as the main correspondent. Additional materials include 1761 business papers that chronicle the finances of the estate, 11 account books, and 6 hunting books. The business letters and account books detail the estate's expense accounts and receipts, as well as the balances for their annual crops, salmon fishing business, and profits derived from the rents collected on their land. The hunting books contain descriptive accounts of the family's hunts and inventories of their hunting dogs.

The third, and final, part of the collection consists of Tailyour family records (bulk post-1815), including 49 letters from various family members in the late-nineteenth and early-twentieth centuries and five letterbooks, kept by Alexander Renny Tailyour and Thomas Renny Tailyour. 4 account books are also present kept by Alexander Renny Tailyour and others. Some of the records concern the First World War, including a group of prisoner-of-war records sent from Germany, and journals kept at home that detail news of the war, and daily domestic activities.

The family history documents include 64 genealogical records and 58 probate records. Many of the genealogical items are brief notes on family history, and sketches of the family tree, including a large family tree that spans several hundred years to the present day. The probate records contain one will from the late-nineteenth century, but are otherwise entirely concerned with John Tailyour's estate in the years immediately after his death.

Of the printed records, Memoirs of my Ancestors (1884), by Hardy McCall is a genealogy of the McCall family, and Tailyour's Marykirk and Kirktonhill's estates are described in two printed booklets, one of which is an advertisement for Kirktonhill's sale in the early-twentieth century. Other printed material includes 14 various newspaper clippings concerning the family over the years, and 12 miscellaneous items.

The illustrations, artwork, and poetry comprise 14 fashion engravings, 12 sailing illustrations, a picture of a hunting cabin, two silhouettes, and a royal sketch, all of which date from the early- to mid-nineteenth century. Kenneth R. H. Tailyour's sketches are represented in two sketch books created in his younger years (1917 and 1920). Loose records of poetry, as well as a book of poems from George Taylor, are in this section.

The 221 photographs are of the Tailyour family from the late-nineteenth to the twentieth century, with the majority falling in the early decades of the twentieth century. Most are portraits of the Tailyour family from the early twentieth century, particularly Kenneth R. H. Tailyour.

The 138 pieces of ephemera are, for the most part, postcards of foxhunts during the nineteenth century. These announce the almost-weekly family foxhunts during the middle years of the nineteenth century. The 19 items of realia, include Robert Taylor's quill pen from 1826.

The audio-visual portion of the collection contains three items: a compact disc with an audio interview of John Dann, Director of the Clements Library, on National Public Radio's "The Todd Mundt Show;" a compact disc with photos of the West Indies; and a collection of photographs of the Tailyour papers in their uncatalogued state, and of the festivities surrounding the acquisition of the collection.

Finally, miscellaneous material of 18 pieces includes Robert Taylor's commonplace book of short stories, letters, and poems; the catalogue of Robert Taylor's books; James Tailyour's 1771 style and form book; and a communion book.