William H. Chadwick was born in Yorkshire, England in 1879. However, in 1882, his father, a wool manufacturer, relocated the family to Massachusetts. Chadwick displayed an early aptitude for art, and after graduating from high school he moved to New York to pursue an artistic career. He enrolled at the Art Students League to study with John H. Twachtman, Kenyon Cox, and William Merritt Chase.

In the summer of 1902, Chadwick made his first visit to the Old Lyme Art Colony located on the coast of Connecticut. Due to its proximity to New York, the village of Old Lyme became a favorite retreat for American artists, including the well-known Impressionist, Childe Hassam. The colony soon became a gathering point for American Impressionists and a popular destination for landscape artists. Over the next seven years Chadwick divided his time between Old Lyme in the summer months and New York during the academic year where he served as the treasurer for the Art Students League. Following his marriage, Chadwick bought a home near the shore in Old Lyme which became his permanent residence in 1915.

From 1924–1926, Chadwick taught at the Telfair Academy in Savannah, Georgia and resided in the city during the school terms. By the time Chadwick was teaching in Savannah, he was working in a distinctive Impressionist style with an emphasis on the effects of light. The painterly, loose brushwork is indicative of a painting done en plein air, in which rapid execution is essential to capturing fleeting atmospheric effects. The works within this collection are from this period and each incorporate a light, sunny color palette and showcase genre scenes of city and country life. Chadwick was one of several northern artists that spent time in Savannah between the late twenties and early forties, and the city welcomed this artistic flowering. The Savannah Art Club actively sought out artists to act as instructors for the new school at the Telfair, attracting Chadwick and Eliot Clark. Other painters, such as Alexander Brook and Andrée Ruellan, arrived in Savannah a decade later and established a small art colony along the Riverfront which they used as a winter retreat. Whatever the circumstances, once they arrived the artists were inspired by Savannah’s historic architecture and picturesque parks, as well as by the untamed natural beauty of the surrounding marshlands. In 1927, the Telfair Academy honored Chadwick by hosting the first, and only, solo exhibition of his career.