Esther Allen Howland, born in Worcester, Massachusetts, was the daughter of Southworth Allen Howland (1800-1882) and Esther Allen Howland (1801-1860). The sister of Charles, Edward, and william Howland. Her mother wrote the cookbook, The New England Economical Housekeeper and Family Receipt Book, which was published in 1844 (and for the next ten years) by her father S. A. Howland.

Howland graduated from Mount Holyoke College (then Mount Holyoke Women's Seminary) in 1847, just 10 years after its opening. Though Mount Holyoke did not celebrate Saint Valentine's Day, students often secretly exchanged poems elaborately scrawled on sheets of paper.

In 1850 her first advertisement appeared in the Worcester Spy. Soon enough she found herself in the position of a businesswoman. She began to import materials from Germany. She also came up with the idea of using silk and embossing lithograph ornaments. With success brought competition. In order to distinguish her valentines Esther began stamping the letter "H" on the back of her cards in red ink along with the price and the letters ‘N.E.V.Co.’ which stood for the name of her company New England Valentine Company. While a simple cards made by her sold only for five cents. Cards that included ribbons, artistic illustrations, hidden doors, gilded lace, and interior envelopes that could hold more secret messages, locks of hair or even engagement rings , sold up to one dollar to fifty dollars. which at the time a considerable amount of money. Esther also created Christmas cards, New Years cards, Birthday cards, Booklets, and May baskets. Esther suffered from a knee injury in 1866 which forced her to be in a wheelchair. In 1870 Esther Howland incorporated her Business as the New England Valentine Company she then continued to work from her home until 1879 when she then moved to a factory. During that same year she published The New England Valentine Co.’s Valentine Verse Book that consisted of thirty-one pages. The book was intended for customers who found a beautiful card but didn't like the verse that was inside. With the book they could choose from a total of 131 verses all printed in red, green, blue, and gold ink and came in 3 different sizes. With their chosen verse they could then paste it over the original verse inside the card that they had bought. In 1879 Esther decided to merge her Business with one of her competitors Edward Taft.

Her valentines became renowned throughout the United States and she was called "The Mother of the American Valentine." Due to her cards being shipped all over the country her Business eventually grossed over $100,000 per year, a considerable sum for that time, and she eventually sold the Business to George Whitney in 1880 in order to take care of her sick father. In 1904 Esther fractured a femur and was bedridden for 8 months. She then died in her home at 9 Adams St in Quincy.