Orange

FLAGG, George W.

1st Biography of George W. FLAGG

Men of Vermont: Illustrated Biographical History of Vermonters & Sons of 
Vermont. Ullery. Brattleboro: Transcript Publishing Company, 1894, pp 139-140 
(portrait p 139)

George W. FLAGG, of Braintree, was born 09 April 1839 in Braintree [Orange 
County, Vermont], son of Austin and Mary E. (HARWOOD) FLAGG. Educated in the 
common schools of Braintree and Randolph Academy [Orange County], he remained 
upon his father's farm until the age of twenty, and afterwards was a day 
laborer until the breaking out of the Civil War [which began in April 1861]. 
In May 1861 he enlisted at Montpelier [Washington County] in Company F, 
Second Regiment Vermont Volunteers, and participated in every engagement in 
which the old Vermont brigade bore part from Bull Run to Appomattox. He was 
constantly on duty, but for one month was disabled by a would received in the 
[battle of] the Wilderness. On 03 May 1864 his brigade was the first to 
enter Petersburgh, when General GRANT advanced on Richmond. Mr. FLAGG 
enlisted as a private, served four years, participated in twenty-five battles 
and was promoted to the rank of sergeant; he as such more than once commanded 
his company in the absence of all the superior officers. He was honorably 
discharged as first lieutenant with brevet captain 25 July 1865. He was in 
command and took home to the state the only company organized in the capital 
of the state during the war. Soon after the close of the war he married and 
settled upon a farm.

Early in life he showed great aptitude for collar and elbow wrestling and has 
wanted, even when a boy, to display this accomplishment at public gatherings. 
He gradually so increased in skill that he was the acknowledged champion of 
the Army of the Potomac. From the age of thirty-five to forty he traveled 
extensively in most of the northern states, giving exhibitions of his 
proficiency, and his only rival was H. M. DUFUR, with whom he had many hard 
fought battles. At the age of eighteen he lost his last fall (for business), 
for fifteen years he knew no difference in men, he could throw any man he 
ever met in five minutes. He traveled through Western New York, where he won 
many matches, also Ohio. He wrestled in almost every town of importance in 
Michigan, where he defeated the renowned Indian chief Tipsico at a back hold 
match. In New England he wrestled for agricultural societies, one of which 
was the Vermont State Fair, also at July 4th gatherings to thousands of 
people under great excitement. In his travels he challenged all comers for 
any amount with perfect confidence. After each campaign of travels he 
returned to work on his farm, never training for a match or series of 
matches. During Mr. FLAGG's wrestling career he doubtless wrestled two 
hundred matches. Athletic sports had a great fascination for him. A game 
that was very popular in his boyhood days, the champion wrestler being the 
lion of the day at all public gatherings. In all of his matches he always 
manifested good cheer towards all, never losing his temper, being strictly 
honest.

Mr. FLAGG now owns three hundred and fifty acres in the east portion of the 
town, it being the second best in town, the production of which he has 
quadrupled in twenty-four years. He is a well known breeder of Cotswold 
sheep and has received many medals and prizes for specimens exhibited at New 
England state and county fairs. He also possesses an excellent orchard, for 
the fruit of which he finds a ready market. As a temperance man none were 
more zealous in the cause than he. In all of his travels he never tasted 
liquor; making speeches in the Legislature in the cause of temperance, never 
tiring in advocating its cause.

On 16 May 1865 Mr. [George W.] FLAGG married Delia A., daughter of Whitman 
and Elmira (SMITH) HOWARD; by her he has had two children: Lester C. and 
Bert C. Mr. FLAGG is a Republican; has been called upon to serve his town in 
many minor offices, and was elected representative to the Vermont Legislature 
in 1886. He received his degrees in Masonry in Phoenix Lodge of Randolph, 
and has joined U. S. Grant Post No. 96, Grand Army of the Republic, of West 
Randolph, and is its present commander. Mr. FLAGG possesses a marked 
personality, is fully six feet in height with the figure of a Hercules; and 
with his jovial good nature, his sturdy strength and endurance, his 
unflinching courage and unselfish patriotism is the typical Green Mountain 
Boy of '76 and '61.



2nd Biography of George W. FLAGG

Encyclopedia Vermont Biography: A Series of Authentic Biographical Sketches 
of the Representative Men of Vermont and Sons of Vermont in Other States. 
Dodge. Burlington: Ullery Publishing Company, 1912, p 190-191

George W. FLAGG, farmer, Braintree, was born 09 April 1839 at Braintree 
[Orange County, Vermont], son of Austin and Mary E. (HARWOOD) FLAGG. 
Educated in the public schools. Enlisted as a private in Company F, Second 
Vermont Volunteers, May 1861; mustered into service the following June; was 
at the battle of Bull Run, McCLELLAN's campaign before Richmond, Antietam, 
first and second battles of Fredericksburg, SHERIDAN's campaign in the 
Shenandoah Valley, Gettsyburg, Winchester, Fisher's Hill, Cedar Creek, and 
others of less note. Served over four years; mustered out in July 1865; was 
first lieutenant, and brevet captain in command of the only company raised in 
Montpelier [Washington County, Vermont]. At the close of the war returned to 
Braintree and engaged in farming; was a breeder of fancy stock for many 
years, which he exhibited at state and county fairs, taking many prizes, 
especially on his Cotswold sheep; for the past seven years has dealt largely 
in Western horses. Was president of the Cotswold Register Association; one 
of the directors and vice president of the White River fair, Bethel [Windsor 
County, Vermont], for many years; director of the Northfield [Washington 
County, Vermont] fair; and has been employed as an expert judge of stock at 
fairs of northern Vermont. Republican; represented Braintree in the 
Legislature 1886; has held many town offices; senator from Orange County 
1910; chairman of committee on military affairs, and member of other 
committees. Past commander Randolph Post, Grand Army of the Republic, of 
Randolph. Has a wide reputation as an athlete and champion wrestler, 
engaging in contests with champions from all America; when thirty-eight years 
old won a champion belt for a three-day contest with twelve wrestlers among 
the best in the U. S.; has wrestled in nearly all the large towns of New 
England, Ohio, Wisconsin, and Michigan; his last contest took place when he 
was sixty-two years old. In 1865 he [George W. FLAGG] married [Miss?] Delia 
A. HOWARD of Braintree [Orange County, Vermont]; she [Delia A. FLAGG] died in 
1910; they had two sons: Lester Gerry; and Bert Clinton, who is deceased.

Submitted by Cathy Kubly