The Old Settlers Association was organized in 1894 in the home of Abbie Gardner Sharp. This organization met each summer at various locations and honored the "Old Settlers" and "Reminiscing" was always on the program. The 1931 registration listed Harriet Kingman Farnham arriving in the county 1858.

The Old Settlers Association met until July 1966, when it combined with the Dickinson County Historical Society.. There were 90 charter members of the organization dedicated to the preservation of Dickinson County history. An ultimate goal was to establish a permanent museum and the first museum opened July 1970 in Okoboji space donated by the Lakes Arts Center. It is now permanently housed in the old Spirit Lake Depot on Highway 9 and 71. Mrs. Faye Peterson was the curator until she retired in 1992.

From Milford Mail Terril Record October 29,1992
By Aubrey LaFoy

It seems impossible to us of the younger generation that Dickinson county and northwestern Iowa has developed from its very first settlement to its present highly improved state within the observation of many persons now living among us.

Having come to Emmet county as a boy, forty years ago, where I came to know many of the earliest settlers of that county; and having practiced medicine in Dickinson county for twenty-seven years, it has been my fortune to have had as patients many of the earliest settlers. It has always been a pleasure to listen to these people recount their early experiences.

Among the pioneers who were, or are among my patients, may be mentioned R.A. Smith, M.J. Smith, W.B. Arnold and wife, Lafe Ring, J.J. Johnson, Edmond Miller, R.T. McCutchin, R.B. Nicol, Olin Pillsbury, A.D. Inman, C. Kessey, H.H. Shipman, Steve Inman, Mr. and Mrs. Horace Cain, Jonaha Welsh, and many others.

At the Milford Fall festival in 1919 and old settlers' Reunion was held. Gunder Matheson being the oldest settler in point of years residence in county, was elected president, and J.F. Ewen secretary. The book was opened and forty-four of the settlers registered. J.W. Cory and F.W. Knight gave short but interesting talks on events of the early days. A very enjoyable two hours was spent renewing old friendships, and living over again in the joys and trials of pioneer times.

At the Milford Festival of 1920 another meeting of the organization was held. The following is a list of those who registered at the last reunion and dates of settlement in the county.

James Skirving, October 1865
W.G. Calkins, April 1869
A.D. Inman, May 1866
C. Kessey, April 1870
J.F. Brett, October 1881
Jessie Brett, October 1890
G. Matheson, June 1859
T.S. Walker, June 1868
Hattie Walker, July 1866
Georgia Holcomb, October, 1868  
Samuel Holcomb, May 1870
Anna Tucker, April 1866
F.Tucker, April 1876
Phebie Henaman, March 1877
Geo. Griffith, July 1875
Lucian G. Winey, June 1869
Esther Weed, August 1871
G.D. Hazzard, October 1878
G.W. Taber, September 1877
S.L. Pillsbury, May 1863
Frances Pillsbury, October 1861
F.A. Heldridge, Juner 1874
C.C. Heldridge, September 1868
A.R. Davidson, June 1866
W.S.Crowell, April 1881
H.U. Arthurr, July 1860
Elmer W. Inman, December 1868
Marcus Snyder, August 1865
J.W. Cory, September 1871
Mrs. Marcus Snyder, October 1874
W.F. Carlton, November 1871
E.D. Carlton, November 1871
Thomas Williams, August 1880
Mrs. Thos. Williams, August 1882
Matha Nicol, June 1886
Mrs. Wallace Smith, February 1866  
Thomas Pegdon, April 1870
H.H. Shipman, September 1871
Abbie Shipman, September 1872
V.A. Arnold, October 1868
Chris H.Horn, September 1871
H.R. Henderson, September 1864
Ida Henderson, September 1862
M. Wadleigh, July 1881
C. Olson, June 1859
Elizabeth Pitcher, August 1882
Edith George, October 1881
Mrs. A.K. Turneaur, October 1881
Mrs. Eli Miller, May 1875
Val Rausch, March 1889
Geo. W. Vetter, March 1889
John S. Blow, January 1883
J.F. Ewen, March 1883
R.M. Davis, April 1884
Bert Wilson, February 1879
Frank Harker, September 1881
T.J. Francis, May 1860
Mrs. T.J. Francis, September 1862
John Swailes, May 1870
Ellsworth Harker, September 1881
Mrs. J.C. Guthrie, July 1881
L.B. Pillsbury, August 1883
Mrs. Vi Free, June 1885
Beulah Heldridge, August 1881
Fred T. Phippin, October 1861
Mary White Case, September 1882
Lizzie Calkins, April 1869
Bessie Pillsbury, June 1888
Inez Miller, July 1868
Sadie Erskine, May 1880
Edith Woods, June 1873
Eli Miller, May 1869
C.C. Calkins, April 1871
Mattie Heldridge, June 1868

From Spirit Lake Beacon September 1st, 1921
By Dr. Q.C. Fuller.

Meeting in 1932

Following is a list of the registration of those who have resided in Dickinson county prior to thirty years ago.

1857-Mrs. O.R. Barber
1858-H.U. Arthur
Mr. and Mrs. James Chapman  
1869-Mary Rausch
1861-F.F. Phippin
Mae O'Farrell
Mrs. Sam Pillsbury
1864-F.E. Henderson
B.P. Henderson
H.R. Henderson
1865-J.L. Clark
1866-Cora Phippin
A.R. Davison
1867-J.L. Cother
Annie Paul
J.W, Kilpatrick
1868-Mrs. C. Tortenson
O.B. Willcox
Pearl Furgerson
Inez Miller
Bertha Rust
E.E. O'Farrell
1869-E.A. Case
Mrs. John Dickerson
W.G. Calkins
Mrs. Ellie Arthur
1870-E.E. Heldridge
Laura Pugh
S.A. Holcomb
1871-Mrs. Addie Welch
Martha Larson
J.W. Cory
Mrs. A. Hakinson
1872-Mrs. Fred Sheldon
Annie Olson
Jonah Welch
R.J. Dare
Frank James
Mrs. Frank Hunt
1973-Mrs. Vesta Nielson
Edith W. Woods
1974-J.E. Ranney
Mrs. J.G. Henderson
1875-Lillian Roat
Eli Miller
Frank Hunt
1876-Mrs. H.R. Henderson
Mrs. Rena LaDoux
Mrs. Tilda Ammundson
C.O. Anderson
Peter Johnson
1877- T, Matheson
Lizzie Calkins
1878-Carl Matheson
A.L. Lodge
Grace A. Middleton
L.W. Owen
G.D. Hazard
1879-P. Woods
I. Mitchell
Mrs. H, M. Wilson
1880-J.E. Ranney
R.S. Carlton
W.F. Tompson
Thomas Williams
B.A. Webb
Mrs. G.L. Webb
J.T. Webb
Mrs. J.L. Cother
1881-Frank Harker
R.K. Harker
W.S. Poland
M.A. Wadleigh
A.A. Beck
Edna Tabor
Abbie Tabor
Mrs. I. Swentson
1882-Mrs. W.F. Wright
Mrs. J.W. Kilpatrick
Mrs. C.C. Harker
C.E. Tabor
Wm. R. Gillette
Esther Winey
Hattie Brewer
Mary White Case
Mary L. Williams
Anna Warburton
George Sherburne
A.O. Stevens
Elizabeth J. Pitcher
G.L. Webb
Fred W. Jones
J.S. McGuire
Frank W. Knight
Mrs. G.N. Sherburne
1883-Lillian Lynn
J.F. Ewen
Mrs. Lenore D. Osburne
1884-C.H. Arthur
Mrs. J.F. Ewen
J.F. Davis
Geo. Wingert
1886-Adda McKiinney
W. Poyzer
G.G. Gregory
Frank Gregory
Ora Gregory
R.A. Paterson
1887-C.J. Gregory
R. Jones
Ray B. Nicol
1888-Grant Lynn
Roscoe Wright
Gerald Owens
Val Rausch
Eva Webb Price
1889- Paul
Mrs. R.A. Peterson
Michael Baschke
Julius Wiech
Edna Donaldson
Mrs. L. Boyenga
Eva Miller
Mr. and Mrs. C.E. Weaver  
Gladys Hunt
1890- Bascon
P.F. DeMuth
Mrs. Isaac Mitchell
F.W. LaDoux
Mrs. M. Albert
1891- Peterson
H. Adkins
Mrs. H. Peterson
Joseph Adkins
Theo Larson
1892-Mrs. Fred Boyer
Fred Stapleton
Mrs. J. Wiech
Mrs. Henry Versluis
Lela M. Naudain
Mrs. Tina Groff
Wm. Wedeking
Amanda Storsteen
Mrs. Mary Hatfield
1893-W.J. Wallace
Mrs. Fred Jones
Mrs. H.E. Luing
Anna Borchard
Mrs. F.W. Knight
Mrs. W.F. Thompson
1894-Lewis Calkins
Q.C. Fuller
E.J. Hamilton
Mrs. A.H. Arthur
1895-Mrs. E.J. Schmidt
Mrs. T.O. Triggs
Eva Phippin
1896-Albin Anderson
Lewis Jones
Helen M. Peterson
Fred Versuis
Mrs. W. Warburton
1897-F.W. Range
C.F. Cline
Mrs. F.W. Range
R. Mandelke
1898- LaFoy
Neal Anderson
Icle Pugh
E.O. Johnson
A.J. Nicol
Anna Nicol
Dagmar Johnson
Mrs. V.V. Tritle
V.R. Tritle
1899- Schmidt
F.L. Upton
Mrs. Esther Johnson
1900-Mrs. A. Erickson
Mrs. L. Calkins
Mrs. Peter Johnson
Mrs. and Mrs.[sic] Geo. Williams
Mrs. B.L. Meyerdirk
1901-Nettie Johnson
L. Paul
Mrs. B.A. Webb
J.E. Johnson
J.A. Wilson
Mrs. Frank Harker
Francis Johnson
1902-Mrs. E.A. James
M.M. Jones
Mrs. Neal Anderson
Valoris Johnson
J.F. Yager
Mrs. J. F, Yager
Mrs. J.W. Frutchey
1903-Mrs. Grace Dare
Mrs. Fred Phippin
LLoyd Place
F. Place

Meeting in 1939

Old Settlers Name Caywood President 1939

150 Old Settlers attend annual Picnic to talk over Old days and enjoy program.

H.E. Caywoood of Lake Park was elected president of the Dickinson County Old Settlers at the annual picnic held Friday at Gull Point state park. Other directors elected were C.E. Gill, Terril, vice president; secretary, Mrs. V.V. Kidd, Spirit Lake; directors, James Smith, Superior; E.G. Mott, Spirit Lake; Mrs. Chet Teal, Lake Park; Mrs. Ray B. Nicole, Milford; and Gaylord Olson, Terril.

Mrs. V.R. Tritle read the following list of pioneers who have passed since the last meeting:

Mrs. Mary Sperbeck Stoerlein
H,A. Stillwell
J.A. Polard
Mrs. Katte Mott McGrew
Mrs. Emily Campbell Sprague   
Mrs. Lena Below Ash
Mrs. Ida Yarnes Willey
Arthur E. Arp
John Harker
Henry Kettleson
W.S. Poyzer
Mrs. W.W. Stow
Mrs. G.N. Sherburn
J.E. Ranney
Mrs. Martha Baldy
Melvin Waugh
Mrs. Val Rausch
W.J. Adkins
Henry Adkins
Mrs. John Lunder
Mrs. A.B. Thorn
Mrs. M.F. Fitzgibbon   
Mrs. Rose M. Davis
R.R. Van Osdal
Harry J. Lewis
Leon P. Flemming
John T. Webb
William Meister
Frank Leupold
Eva F. Phippin
Francis Carlton Dowd
Mrs. H.F. Kruse
G.R. Bryan
Ira Fox
William J. Arthur
Nelson Olson
J.T. Winter
Edward Holding
B.K. Bradfield
Mrs. G.R. Chesnut
Frederick Stratman
Geo. F. Arp
Mrs. E.P. Atkins

From Milford Mail August 24, 1939

Old Timers Recall Days When fishing was Work 1934

Also mention a lot of other Pioneers

From Milford Mail September 27, 1934
By Harvey S. Abbott and Lorenzo Sperbeck

Dickinson County Iowa Genealogy - The IAGenWeb Project