History Makers: Doolittle family left its mark on Cheshire, nation

History Makers: Doolittle family left its mark on Cheshire, nation

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They are listed, in the opening paragraphs of “Landmarks of Old Cheshire,” as one of what you might call the “founding families” of the small farming community that would eventually grow into the Town of Cheshire. One local school is adorned with the family name, while at the Cheshire Historical Society, a large portrait of a family war hero hangs prominently as part of a special collection.

And American history cannot be told without the help of one Doolittle’s skill and artistry.

The Doolittles are as much a part of Cheshire history as anyone, spanning the decades, indeed the centuries of the town’s early existence.

Yet, while each family member had a hand in turning Cheshire into a vibrant and growing community, three seem to stand out.

In modern day, the one most familiar to local residents would be Frederick Doolittle, though many may not know that he is, in fact, the inspiration behind Doolittle Elementary School.

Frederick was born in 1849, one of four boys. He lived through the tumult of the mid-19th Century in America, as the country careened towards war. When conflict did break out, the then-12 year old was likely eager to help in some manner.

Yet, while the war saw many young men enter, despite barely being out of their teens, Frederick was spared serving.

With his older brothers heading to the front lines, he had to stay behind and help with the farm, as an article from The Cheshire Herald, on the occasion of Doolittle School’s dedication in January of 1963, explained.

“After the war his brothers went their own ways, and he stayed on to help with and later to run the farm, and to take care of his aging parents,” the article explained. “Even with all the work, he managed to get in a term or two at the Cheshire Academy, but his formal education ended there. However, he never stopped studying.”

It would be that lifelong dedication to learning that would ultimately earn Doolittle the honor of having a school named after him.

“School-teaching in those days was strictly a strong man’s job, and when there was a shortage of competent males he took over and taught in various district schools for several years,” the article continued. “He later was elected to the School Board in 1889 and served for thirty years, twenty-seven as Secretary, and became an official school visitor. He introduced some innovations … (including) small non-textbook libraries of donated books, and the practice of taking Cheshire classes to see the State Capitol, and some museums. When the first phonographs came to Cheshire, he said he didn’t care much for the contraption as a musical instrument, but he thought it could be a Godsend to a history teacher, if she could play the lesson over for an hour or two. It is believed an attempt was actually made to cut some old cylindrical records of important dates.”

It appears that even Mrs. Doolittle got in on the action, to the consternation of some.

“… Mrs. Doolittle was criticized by some men for urging the women to take advantage of the privilege (of gaining an education). She replied that every woman in the Town of Cheshire wanted her children to marry better than she did, and a good school system was a step in that direction.”

Doolittle died in 1922, more than 40 years before he was to be honored.

Well before that, another Doolittle was receiving praise - perhaps the most famous of all in the family tree, Amos Doolittle. Born to Ambrose and Martha Doolittle, he was one of 15 children who grew up in the two-story saltbox home that once stood near where the current Masonic Temple Lodge is on Route 10.

Amos apprenticed as a youth with New Haven silversmith Eliakim Hitchcock, mastering a craft that would eventually cement him in the annals of early American history. And much like the country itself, Amos’ journey into the history books began at Lexington and Concord.

As a 20 year old, Doolittle was, like many of his friends and family, full of fervor for independence, and when conflict broke out between British troops and patriots, Doolittle, under the command of Captain Benedict Arnold, responded to the Lexington Alarm in April of 1775.

However, by the time Doolittle, accompanied by his friend and artist Ralph Earl, arrived, the hostilities had ended. The two decided to visit the battlefields, interviewed those who had witnessed the conflict, and Earl began to compose sketches of what the skirmishes had looked like.

Upon returning to New Haven, Amos put his own skills to work, making four unique engravings out of the Earl sketches. Twelve by 18 inches in size, the set sold for 6 shillings plain or 8 shillings colored.

As the book “Landmarks of Old Cheshire” explains, Amos’ work has taken its place beside another notable Revolutionary War figure as some of the most important of the time.

“These engravings stand second only to Paul Revere’s engravings of the landing of British troops in Boston (1768) and the Boston Massacre (1770) as the earliest historical prints of the Revolutionary War…one of the finest complete sets may be seen at the Connecticut Historical Society in Hartford.”

In 1994, at the time of “Landmarks” reprinting, a set of the engravings had just been sold at auction, for $84,000.

Yet, while Doolittle’s most important contribution was made through his skill as an artist, he eventually found the “action” he had been seeking on that day in Lexington and Concord, as William Dunlap explained in his “History of the Rise and Progress of the Arts of Design in the United States,” published in 1834.

“When the British invaded New Haven in July, 1779, Amos Doolittle was involved in the defense of the bridge across the Mill River at Hotchkissville (Westville). As the British were soon able to ford the stream lower down, the patriots fell back toward New Haven. Doolittle headed for home where his wife lay ill. Fortunately the Doolittles had a house guest, an Englishwoman, who demanded that the entering British troops post a guard at the Doolittle home. Although Doolittle’s musket was discovered, the Englishwoman convinced the guard that Doolittle only had the gun because it was required by law and that he indeed was a friend to George III. Quick thinking on the part of this overseas visitor is all the saved Doolittle from the prison ships of New York.”

Amos Doolittle died in 1832.

Thirty years later, it would be another Doolittle making a name for himself as a proud defender of freedom and union.

Edward Doolittle was born in 1838, six years after Amos’ passing. His father, Warren Doolittle, and mother, Anna, lived on Depot Street, which is now West Main.

Warren, along with his neighbor, Arad Welton, was a director of the nearby Cheshire Manufacturing Company, which would later become the Ball & Socket Factory.

Edward, like many boys of his age in Cheshire, would be schooled at the Episcopal Academy, now Cheshire Academy. He enrolled when he was 10.

Four years later, as a student at the Academy, Edward would pen a short essay on what it meant to be a good man. The original document exists to this day and is part of the Cheshire Historical Society collection.

“He must (show) obedience both towards his parents and teachers,” Doolittle wrote, “but the first he has to obey is his parents (and) the parents ought to take good care of him so that when he grows up he will be a good and useful member of society.”

“He must always be diligent (at) whatever … occupation he may follow,” Doolittle continued, “and must be honest in his doings with his fellow man.”

Just a teen, Edward’s words would ring true later in life when, in 1862 at the age of 24, he would enlist as a member of the 20th Regiment Company A. He would attain the rank of lieutenant and, according to his superiors and subordinates alike, establish himself as a brave soldier and trusted leader.

Both would be on display during two of the war’s most important and bloodiest battles, which Col. Samuel Ross, Commander of the 5th Reg. CT, alluded to in discussing Edward some time later.

“His personal gallantry at Chancellorsville and Gettysburg forms a proud memoir in our history,” said Ross.

Chancellorsville, fought in April and May of 1863, is remembered for several reasons. First, it was considered by many military historians to be Confederate General Robert E. Lee’s “perfect battle,” in which, by making the bold move to divide his forces, took the more timid Union generals’ by surprise and won the engagement. It was also the battle in which famous Confederate Lt. General Thomas “Stonewall” Jackson was killed, a victim of friendly fire. And perhaps most noteworthy, Chancellorsville was one of the most costly engagements of the war.

Gettysburg followed a few months later, in early July of 1863, and would cost even more soldiers their lives.

But unlike Chancellorsville, which was a Confederate victory, Gettysburg would be won by the Union, turning away Lee’s desperate attempt to invade the north over a three-day conflict.

Edward survived both. Yet in the end, he could not survive the war’s deadliest foe: disease.

In the late fall of 1863, Edward contracted typhoid fever while serving as a guard for the lines of communication.

He suffered a few weeks but eventually succumbed to the disease in December of that year.

After the war, a group, the Grand Army of the Republic (G.A.R.) was created by veterans with departments and posts established in each state of the Union. The G.A.R. Post 5 in Cheshire was named after Doolittle.

In 1866, during the dedication of the Soldier’s Monument in Cheshire, Col. W.B. Wooster eulogized Edward.

“He was a gentleman of education, refinement, and purity, a patriot soldier….A man who never shrank from duty, true to himself, true to his comrades, his country and his God…he died lamented by all.”


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