The Kent County side of Milford was first settled in 1680 by Henry Bowan on what was known as the Saw Mill Range. A century later the Reverend Sydenham Thorne built a dam across the Mispillion River to generate power for his gristmill and sawmill. Around the same time, Joseph Oliver laid out the first city streets and plots nearby on a part of his plantation. Soon a number of homes and businesses appeared along Front Street and Milford was born. The city was incorporated February 5, 1807.
During much of the twentieth century Milford served primarily as the commercial center for much of southern Delaware's large agricultural community. Today Milford's historic downtown has become a renewed center of community life hosting upmarket boutiques, art galleries, restaurants and a community theatre. Celebrating the importance of the Mispillion River, downtown Milford is host to several regional events each year including the Riverwalk Freedom Festival and the Bug & Bud Festival. Residents and visitors alike can enjoy the natural resource as they walk, bike or run along the Mispillion Riverwalk, a series of pedestrian and bicycle paths that hug the banks of the Mispillion River.