Guide to the Collection

Collection Summary


This collection consists of the papers of Henry Winchester Cunningham and Mary May (Hayward) Cunningham, including correspondence, notes, genealogical material, a collection of historical documents, and printed matter.

Biographical Sketches

Henry Winchester Cunningham (1860-1930) was the son of James Henry and Lucinda Stearns (Winchester) Cunningham. He attended Roxbury Latin School and graduated from Harvard College in 1882. In 1889, he married Mary May Hayward (1863-1929), daughter of Isaac Davenport Hayward and Mary Vose Hayward of Milton, Mass. The couple had no children.

Mary May Cunningham inherited the Wakefield Estate in Milton after her mother's death in 1901. She initially held the property with her half-brother George Griswold Hayward, Isaac Davenport Hayward's son by his first wife, and her brother Roland Hayward, the child of his second wife. George sold his inheritance to his half-brother and sister in 1902, and Roland bequeathed his share to his sister when he died in 1906. Henry and Mary Cunningham split their time between households in Boston and Milton, using the Mansion House in Milton as their summer estate.

When Mary May Cunningham died in 1929, she divided her property between her cousin Henry P. Binney (1863-1940) and her nephew Griswold S. Hayward. Henry Binney was the son of her father's sister Josephine and her husband Henry Binney (1838-1878). Griswold was the surviving son of her half-brother George Griswold Hayward.

Henry W. Cunningham was deeply interested in the study of New England history and genealogy. He was active in the management of local historical societies and served for many years as corresponding secretary of the New England Historic Genealogical Society. Henry died in 1930.


Graham, Shelby, Annie Rotner, and Claire Dempsey. "Biographies of Wakefield Property Owners." Mary M .B. Wakefield Charitable Trust: History and Background, June 2007. October 2006.

Graham, Shelby, Annie Rotner, and Claire Dempsey. "Title History of the Wakefield Property, Milton, MA." Mary M. B. Wakefield Charitable Trust: History and Background, June 2007. October 2006.

Collection Description

The Cunningham family collection consists of the papers of Henry Winchester Cunningham (1860-1930) and Mary May (Hayward) Cunningham (1863-1929). Included are personal papers of Henry W. Cunningham documenting his work with the Colonial Society of Massachusetts, Harvard College (Class of 1882), the New England Historic Genealogical Society, and other organizations; papers related to his estate and to family property in Manchester and Milton, Mass.; notes, correspondence, printed matter, and other genealogical material on the Binney, Cunningham, Davenport, Hayward, May, and related families; and a number of historical items collected by Henry. Among the genealogical papers is a diary of merchant, farmer, and state senator Elijah Vose, 1831-1836. Among the historical items are diaries of Samuel Checkley, John Kneeland, and John Price; single letters by Thomas Pownall, Jeffery Amherst, Jonathan Belcher, and Jared Sparks; papers related to the firm West & Blake; and papers related to the smallpox vaccination in Milton, Mass.

The collection also contains a recipe book and estate papers of Mary May Cunningham, as well as printed material on the history of Milton, some ancestors and relations of the Cunninghams, and other historical and genealogical subjects.

Acquisition Information

On deposit from the Mary M. B. Wakefield Charitable Trust, September 2011.

Custodial History

The Henry P. Binney family papers, Cunningham family papers, Davenport family papers, Joseph H. Hayward family papers, and Mary M. B. Wakefield papers originally formed one large collection at the Wakefield Estate in Milton, Mass. Before the papers were deposited at the MHS, they were separated into these five separate but closely related collections.

Detailed Description of the Collection

I. Henry W. Cunningham papers, 1735-1951

A. Personal papers, 1882-1930

This subseries contains Henry W. Cunningham's personal correspondence; papers of various organizations with which he was involved; papers related to Cunningham family properties in Manchester and Milton, Mass.; and estate papers.

Correspondence, 1905-1926

Box 1Folder 1

Organizational papers, 1882-1913

Arranged alphabetically.

Box 1Folder 2
Club of Odd Volumes, 1912-1913

Included are letters, notes, and clippings related to the club, acquisitions, members, and lectures.

Box 1Folder 3-4
Colonial Society of Massachusetts, 1900-1913

Included are notes, lists, and correspondence related primarily to dinners of the society, as well as to membership and other matters.

Box 1Folder 5-11
Harvard College, 1882-1908

Included are letters, notes, printed matter, financial material, and other papers related to Cunningham's work as secretary of the Harvard Class of 1882, including papers related to the Harvard commencement of 1907, at which Cunningham served as chief marshal, as well as an 1882 pencil sketch of Cunningham by his classmate William Winthrop Kent (1860-1955).

Box 1Folder 12
Home for Aged Women, 1911-1912

Included are notes of meetings, minutes, and a biography of late president Alfred S. Woodworth.

Box 1Folder 13-17
New England Historic Genealogical Society, 1905-1912

Included are notes, printed matter, and correspondence.

Property and estate papers, 1902-1930

Box 2Folder 1-5
Papers related to the Manchester, Mass. property, 1906-1913

Included is correspondence with tenants and contractors, bills and receipts, tax and utility records, notes, printed matter, and other papers related to the Cunningham house and property in Manchester.

Box 2Folder 6-16
Papers related to the Milton, Mass. property, 1903-1929

Included are letters, notes, accounts, tax and utility records, bills and receipts, printed matter, specifications for work, agreements, returns, maps, and other papers related to the Cunningham house and property in Milton.

Box 2Folder 17-19
Estate papers, 1902-1930

Included is Henry W. Cunningham's will, a copy of his birth certificate, printed obituaries, and appraisals of his estate.

Miscellaneous notes and writings, 1916-1917

Included are writings and sketches related to James Edward Alexander's expedition to Africa in 1836-1837, as well as a translation about French history.

Box 2Folder 20

B. Genealogical papers, 1823-1951

Arranged alphabetically by family.

This subseries contains genealogical papers on the Cunningham family and other families to which they are related, collected by Henry W. Cunningham. Due to the interrelated nature of the material, there is a some overlap of subject matter across sections.

Note: Series III (Printed material) contains some pamphlets and other printed items related to genealogy and individual family members.

Box 2Folder 21-23
Binney family, 1910-1935

Included are writings, correspondence, typescript copies of correspondence, and printed matter.

Box 3Folder 1-2
Cunningham family, 1823-1951

Included are letters, notes, papers concerning the Cunningham coat of arms, and clippings, as well as some original documents related to Horace, Andrew, John, and Helen Cunningham, 1823-1873.

Box 3Folder 3-12
Davenport family, 1905-1929

Included are notes on deeds and property owned by the Davenports, a detailed family history covering five generations of the family, a pencil sketch, and miscellaneous notes and papers.

Box 3Folder 13
Goddard family, undated

Included are notes about the history of the Goddard family in Brookline, Mass.

Hayward family

The Hayward family genealogical papers consist primarily of notes by Henry W. Cunningham, but also include a significant amount of correspondence with Mabel Hope Kingsbury (1927-1930), as well as letters of Walter C. Belcher, Marion S. Arnold, Huldah E. Henshaw, and others; clippings and other printed matter; poems; a book of pedigree diagrams of the related families filled out by Cunningham; extracts of Hayward family deeds; material on the Henshaw family connection; property maps; a detailed family history; papers related to the Hayward coat of arms; and typescript copies of letters by family members.

Box 3Folder 14-22
Box 4Folder 1-15
Box 4Folder 16
Henshaw family, undated

Included is a detailed history of the Henshaw family and a typescript biography of Lemuel Shaw.

Box 4Folder 17-18
May family, undated

Included is a detailed history of the May family, typescript copies of correspondence, and a Samuel May family tree.

Vose family

Included are genealogical notes, a cutslip autograph and diary of Elijah Vose, and a printed obituary of Judge Henry Vose. The diary, kept at Dorchester, Mass. from 1831-1836, describes Elijah Vose's farming and gardening, work with the Massachusetts Horticultural Society and the First Church in Dorchester, and service as a Massachusetts state senator. Accompanying the diary is a note by A. P. Everett describing its discovery and leaving it to Henry W. Cunningham.

Box 4Folder 19
Papers, undated and 1869
Box 7Folder 11
Elijah Vose diary, 1831-1836, with A. P. Everett note, Apr. 1907
Box 4Folder 20
Williams family, undated

Included is a detailed history of the Williams family.

Box 4Folder 21
Winchester family, 1916-1918

Included are letters and notes about the Winchester family and their coat of arms.

Box 4Folder 22
Miscellaneous genealogical notes and clippings, undated and 1923

C. Historical collection, 1735-1914

Arranged chronologically.

This subseries consists of original historical documents collected by Cunningham.

Box 4Folder 23
Diary of Rev. Samuel Checkley of Boston, Mass., kept in The New-England Diary: Or, Almanack..., 1735

Published as Diary of the Rev. Samuel Checkley, 1735 (Cambridge, Mass.: J. Wilson and Son, 1909). The printed pamphlet is located in Series III (Printed material).

Box 4Folder 24
Account of charges for an eight-oared barge built by order of John Henry Bastide, chief engineer for North America, for the expedition against Louisbourg, 28 June 1758

Signed by Edward Grant, Nathaniel Glover, and Thomas Hancock.

Box 4Folder 25
Letter from Gov. Thomas Pownall to Mr. Townshend about a power of attorney, with memoranda on verso, [ca. 1760?]
Box 4Folder 26
Letter from Gen. Jeffery Amherst to Thomas Hancock about passage for supernumeraries, 30 Aug. 1761
Box 5Folder 1
Journal of John Kneeland, 1769

Included are notes by Cunningham about Kneeland and the journal.

Box 5Folder 2
Letter from Jonathan Belcher to Thomas Hancock, 5 Dec. 1763, with The Boston Gazette, and the Country Journal, 22 Mar. 1784
Box 5Folder 3-7
West & Blake papers, 1799-1820

Included are accounts, receipts, correspondence, promissory notes, and other financial papers related to the business of West & Blake. Among the individuals and companies represented are Andrew Cunningham, Daniel Mallory & Co., Edmund Baylies, Davis B. Lawler & Co., David West, John West, Lincoln Edmands, and James S. Lovell. Included is correspondence between John West and Andrew Cunningham.

Box 5Folder 8-9
Papers related to smallpox vaccination in Milton, Mass., 1809-1811

Included are letters, resolutions, certifications of inoculation, reports, and other papers. Among the individuals represented are Thomas Welsh, Amos Holbrook, Oliver Houghton, Stephen Horton, Benjamin Russell, and Isaac Davenport. Also included is a letter from Charles E. Goodspeed to Cunningham about the papers, 31 July 1914.

Box 5Folder 10
Journal/memoranda book of John Price, 1850-1891

John Price was the town clerk of Manchester, Mass. Included are clippings about the item, 1909.

Box 5Folder 11
Letter from Jared Sparks to Joseph Green Cogswell introducing James Coolidge Carter, 20 July 1850

Included is a letter from James C. Carter to Cunningham, 15 May 1901, as well as obituaries of Carter (1905) and notes.

Box 5Folder 12
Letter from Joshua Bates to William Roper, 10 Oct. 1850

Included is correspondence of Henry W. Cunningham about Bates, 1901.

II. Mary May Cunningham papers, 1920-1929

Box 5Folder 13
Recipe book, ca. 1920s
Box 5Folder 14-15
Estate papers, 1924-1929

Included are Mary May (Hayward) Cunningham's will, a copy of her birth certificate, printed obituaries, and the appraisal of her estate.

III. Printed material, 1805-1948

Arranged alphabetically by author.

This series consists primarily of printed pamphlets on genealogical and historical subjects, both owned and written by Henry W. Cunningham. Also included are a few books and miscellaneous clippings.

Box 5Folder 16
Ames, Ellis, comp. History of the Redman Farm, So Called, and of the Title Thereto, Situate in Canton, Norfolk County, Massachusetts, Now Mostly Owned by Henry L. Pierce, Esq. of Boston. Boston: William Bense, 1870.
Box 5Folder 17
Batchelder, Samuel Francis. Harvard Hospital-Surgeons of 1775: A Study in the Medical History of the American Revolution. Cambridge, Mass.: [s.n.], 1920. [original and reprint]

Included is material on Dr. Lemuel Hayward.

Box 5Folder 18
Bimbo. The Pleasures of Yachting; Addressed to Col. W. P. Winchester, by His Friend Bimbo. Boston: Eastburn's Press, 1849.
Box 5Folder 19
Bowles, Francis Tiffany. The Loyalty of Barnstable in the Revolution. Cambridge, Mass.: John Wilson and Son, 1924.
Box 5Folder 20
Centennial Gathering of the Hayward Family, with Address by George W. Hayward, and Poem, by Almira L. Hayward. Taunton, Mass.: John S. Sampson, 1879.
Box 5Folder 21
A Collection of Papers Relative to the Transactions of the Town of Milton, in the State of Massachusetts, to Promote a General Inoculation of the Cow Pox, or Kine Pock, as a Never Failing Preventive Against Small Pox Infection. Boston: J. Belcher, 1809.
Box 5Folder 22
The Cow Pox Act with the Order of the Legislature; and a Communication, Relative to the Subject, From the Selectmen of the Town of Milton. Boston: Joshua Belcher, 1810.
Box 5Folder 23
Cunningham, Edward. The "Sister Ann": A Milton Romance of the Last Century. Boston: Rockwell and Churchill, 1873.
Box 5Folder 24
Cunningham, Henry Winchester. Andrew Cunningham of Boston and Some of His Descendants: A Brief Genealogy. Boston: [s.n.], 1901. [2 copies]
Box 5Folder 25
Cunningham, Henry Winchester. Brief Sketch of the Old Milton Church, Its Ministers and Meeting Houses, 1678-1928. [Milton, Mass.: s.n.], April 1928. [4 copies]
Box 5Folder 26
Cunningham, Henry Winchester, ed. Diary of the Rev. Samuel Checkley, 1735. Cambridge, Mass.: John Wilson and Son, 1909.

The original manuscript diary is located in Series I.C. (Historical collection).

Box 6Folder 1
Cunningham, Henry Winchester. John Winchester of New England and Some of His Descendants. [Boston: s.n.], 1925.
Box 6Folder 2
Cunningham, Henry Winchester, ed. Journal of Lieutenant-Colonel Joseph Vose, April-July, 1776. Cambridge, Mass.: John Wilson and Son, 1905. [3 copies]
Box 6Folder 3
The First Four Meeting Houses of Milton, Mass., Covering a Period of Two and a Half Centuries. [Milton, Mass.]: John A. Tucker, 1908.
Box 6Folder 4
Foran, George J. In Memoriam: Washington and Harriet Fowle Snelling, Boston, Massachusetts. [Boston: s.n.], 1921.
Box 6Folder 5
A Genealogy of the Descendants of John May Who Came From England to Roxbury in America, 1640. Boston: Franklin Press; Rand, Avery & Co., 1878.
Box 6Folder 6
Hammond, Otis Grant. Tories of New Hampshire in the War of the Revolution. Concord, N.H.: New Hampshire Historical Society, 1917.

Included is a letter from Otis G. Hammond to Henry W. Cunningham.

Box 6Folder 7
MacPherson, James, trans. The Poems of Ossian, the Son of Fingal. Vol. 2. Edinburgh: Thomas Oliver, 1805.
Box 6Folder 8
Milton Cemetery: A Catalogue of the Proprietors of Lots, Together With a Record of Ancient Inscriptions on All Tablets in the Cemetery Prior to and Including A.D. 1800. Boston: David Clapp & Son, 1883.
Box 6Folder 9
Le Nouveau Testament de Notre Seigneur Jesus-Christ. London: Baker and Fletcher, 1807.
Box 6Folder 10
Park, Lawrence. Major Thomas Savage of Boston and His Descendants. Boston: David Clapp & Son, 1914.

Included is a letter from Lawrence Park to Henry W. Cunningham.

Box 7Folder 1
Proceedings of the Stoughton Historical Society, April 19, 1899, at the Dedication of the Memorial Stone Marking the Location of the First House Built in Stoughton. Stoughton, Mass.: [Stoughton Historical Society], 1900.
Box 7Folder 2
Register of Marriages in Milton, Mass. From the Diary of Rev. Peter Thacher, 1686-1727. Boston: David Clapp & Son, 1883.
Box 7Folder 3
Sanford, Enoch. Biographical Sketch of the Centenarian, Mrs. Abigail Alden Leonard, of Raynham, Mass. Raynham, Mass.: [s.n.], 1887. [2 copies]

Abigail Alden Leonard was Henry W. Cunningham's great-great-grandmother.

Box 7Folder 4
Scott, Henry Edwards. "Henry Winchester Cunningham, A.B." The New England Historical and Genealogical Register. Vol. 85. Boston: New England Historic Genealogical Society, July 1931.
Box 7Folder 5
Teele, A. K., ed. The History of Milton, Mass., 1640 to 1887. Boston: Rockwell & Churchill, [1887].
Box 7Folder 6
Items removed from The History of Milton, Mass., 1901-1930

Included are clippings, notes, correspondence, and maps.

Box 7Folder 7
Ware, Horace E. The Powder Mill on the Neponset; Its Importance to the Colony in Philip's War. [Milton, Mass.: s.n.], 1901.
Box 7Folder 8-10
Miscellaneous printed matter, 1830-1948

Preferred Citation

Cunningham family papers, on deposit from the Mary M. B. Wakefield Charitable Trust, Massachusetts Historical Society.

Access Terms

This collection is indexed under the following headings in ABIGAIL, the online catalog of the Massachusetts Historical Society. Researchers desiring materials about related persons, organizations, or subjects should search the catalog using these headings.


Amherst, Jeffery Amherst, Baron, 1717-1797.
Binney family--Genealogy.
Checkley, Samuel, 1696-1769.
Cunningham family--Genealogy.
Cunningham, Henry Winchester, 1860-1930.
Cunningham, Mary May Hayward, 1863-1929.
Davenport family--Genealogy.
Hayward family--Genealogy.
Kneeland, John, 1748-1831.
May family--Genealogy.
Pownall, Thomas, 1722-1805.
Price, John.
Sparks, Jared, 1789-1866.


Colonial Society of Massachusetts.
Harvard College (1780- ). Class of 1882.
New England Historic Genealogical Society.
West & Blake.


Milton (Mass.)--Genealogy.
Milton (Mass.)--History.
Real property--Massachusetts--Manchester.
Real property--Massachusetts--Milton.

Materials Removed from the Collection

Photographs from this collection have been removed to the MHS Photo Archives.