North Milford Village was platted in 1838 by Aaron Phelps, who also dammed Pettibone Creek to create the still extant millponds.

However, by the early 1840s Phelps ran into financial difficulties and sold out to the Hebbard brothers, who established an industrial park in North Milford.

The railroad came through Milford in 1871, causing a building boom both in the industrial and commercial enterprises now provided with an easy mode of transport.

The residential section of town also expanded greatly, with Victorian houses joining the previous Greek Revival structures.

In the period after World War II, Milford has avoided the urban renewal process, leaving a healthy cross-section of historical structures within the district intact.