Remington was born in Canton, New York in 1861 to Seth Pierrepont Remington (1830–1880) and Clarissa "Clara" Bascom Sackrider (1836–1912). His paternal family owned hardware stores and emigrated from Alsace-Lorraine in the early 18th century. His maternal family of the Bascom line was of French Basque ancestry, coming to America in the early 1600s and founding Windsor, Connecticut. Remington's father was a Union army officer, a colonel, in the American Civil War whose family had arrived in America from England in 1637. He was a newspaper editor and postmaster, and the family was active in local politics and staunchly Republican. One of Remington's great-grandfathers, Samuel Bascom, was a saddle maker by trade, and the Remingtons were fine horsemen. Frederic Remington was related by family bloodlines to Indian portrait artist George Catlin and cowboy sculptor Earl W. Bascom. Another noted western artist related to Remington through the Bascom family is Frank Tenney Johnson, the "father of western moonlight painting."
Frederic Remington was also a cousin to Eliphalet Remington, founder of the Remington Arms Company, which is considered America's oldest gunmaker. He was also related to three famous mountain men—Jedediah Smith, Jonathan T. Warner and Robert "Doc" Newell. Through the Warner side of his family, Remington was related to General George Washington, America's first president.
Remington's ancestors fought in the French and Indian War, the American Revolution, the War of 1812 and the American Civil War.
Colonel Remington was away at war during most of the first four years of his son's life. After the war, he moved his family to Bloomington, Illinois for a brief time and was appointed editor of the Bloomington Republican, but the family returned to Canton in 1867. Remington was the only child of the marriage, and received constant attention and approval. He was an active child, large and strong for his age, who loved to hunt, swim, ride, and go camping. He was a poor student though, particularly in math, which did not bode well for his father's ambitions for his son to attend West Point. He began to make drawings and sketches of soldiers and cowboys at an early age.
The family moved to Ogdensburg, New York when Remington was eleven and he attended Vermont Episcopal Institute, a church-run military school, where his father hoped discipline would rein in his son's lack of focus and perhaps lead to a military career. Remington took his first drawing lessons at the Institute. He then transferred to another military school where his classmates found the young Remington to be a pleasant fellow, a bit careless and lazy, good-humored, and generous of spirit, but definitely not soldier material. He enjoyed making caricatures and silhouettes of his classmates. At sixteen, he wrote to his uncle of his modest ambitions, "I never intend to do any great amount of labor. I have but one short life and do not aspire to wealth or fame in a degree which could only be obtained by an extraordinary effort on my part". He imagined a career for himself as a journalist, with art as a sideline.
Remington attended the art school at Yale University, studying under John Henry Niemeyer. Remington was the only male student in his freshman year. He found that football and boxing were more interesting than the formal art training, particularly drawing from casts and still life objects. He preferred action drawing and his first published illustration was a cartoon of a "bandaged football player" for the student newspaper Yale Courant. Though he was not a star player, his participation on the strong Yale football team was a great source of pride for Remington and his family. He left Yale in 1879 to tend to his ailing father, who had tuberculosis. His father died a year later, at age fifty, receiving respectful recognition from the citizens of Ogdensburg. Remington's Uncle Mart secured a good paying clerical job for his nephew in Albany, New York and Remington would return home on weekends to see his girlfriend Eva Caten. After the rejection of his engagement proposal to Eva by her father, Remington became a reporter for his Uncle Mart's newspaper, then went on to other short-lived jobs.
Living off his inheritance and modest work income, Remington refused to go back to art school and instead spent time camping and enjoying himself. At nineteen, he made his first trip west, going to Montana, at first to buy a cattle operation then a mining interest but realized he did not have sufficient capital for either. In the American West of 1881, he saw the vast prairies, the quickly shrinking buffalo herds, the still unfenced cattle, and the last major confrontations of U.S. Cavalry and Native American tribes, scenes he had imagined since his childhood. He also hunted grizzly bears with Montague Stevens in New Mexico in 1895. Though the trip was undertaken as a lark, it gave Remington a more authentic view of the West than some of the later artists and writers who followed in his footsteps, such as N. C. Wyeth and Zane Grey, who arrived twenty-five years later when much of the mythic West had already slipped into history. From that first trip, Harper's Weekly printed Remington's first published commercial effort, a re-drawing of a quick sketch on wrapping paper that he had mailed back East. In 1883, Remington went to rural Kansas, south of the city of Peabody near the tiny community of Plum Grove, to try his hand at the booming sheep ranching and wool trade, as one of the "holiday stockmen", rich young Easterners out to make a quick killing as ranch owners. He invested his entire inheritance but found ranching to be a rough, boring, isolated occupation which deprived him of the finer things of Eastern life, and the real ranchers thought of him as lazy. In 1884, he sold his land.
Remington continued sketching but at this point his results were still cartoonish and amateur. After less than a year, he sold his ranch and went home. After acquiring more capital from his mother, he returned to Kansas City to start a hardware business, but due to an alleged swindle, it failed, and he reinvested his remaining money as a silent, half-owner of a saloon. He went home to marry Eva Caten in 1884 and they returned to Kansas City immediately. She was unhappy with his saloon life and was unimpressed by the sketches of saloon inhabitants that Remington regularly showed her. When his real occupation became known, she left him and returned to Ogdensburg. With his wife gone and with business doing badly, Remington started to sketch and paint in earnest, and bartered his sketches for essentials.
He soon had enough success selling his paintings to locals to see art as a real profession. Remington returned home again, his inheritance gone but his faith in his new career secured, reunited with his wife and moved to Brooklyn. He began studies at the Art Students League of New York and significantly bolstered his fresh though still rough technique. His timing was excellent as newspaper interest in the dying West was escalating. He submitted illustrations, sketches, and other works for publication with Western themes to Collier's and Harper's Weekly, as his recent Western experiences (highly exaggerated) and his hearty, breezy "cowboy" demeanor gained him credibility with the eastern publishers looking for authenticity. His first full-page cover under his own name appeared in Harper's Weekly on January 9, 1886, when he was twenty-five. With financial backing from his Uncle Bill, Remington was able to pursue his art career and support his wife.