- Prior to the arrival of the Europeans, this area was home to the Huron/Ouendat nations, who were considered one of the most advanced nations in North America. The Jesuits arrived in the 1600s, and the British followed shortly thereafter.
- Midland was eventually settled by farming families in the 1840's, and was known by several names including Mundy's Bay, Hartley's Landing, and Aberdare (named by the first postmaster, Mr. Thomas Gladstane).
- In November of 1871, the Midland Railway Corporation of Port Hope, Ontario, selected Midland as its western port and terminus. Adolphe Hugel and George Cox formed the Midland Land Company and purchased most of the acreage in the area from various farming families. In 1872, they had Peter Burnett survey the new village site, complete with large lots, wide roads and big plans for the future. They named the new community "Midland City." In 1875, the Chew brothers established a grist mill.
- Midland soon reached a population of over 1,000 and was incorporated into a village on October 24, 1878.
- On July 1, 1879, the completed railroad was officially opened for commercial and passenger service. In 1881, the first large grain elevator was completed and regular commercial shipping began.
- Unprecedented business growth continued to the point that the village status was upgraded to incorporation as a Town on January 6, 1890. A local consortium of business leaders headed by James Playfair, David Pratt and Douglas White, to name only three, was responsible for continued expansion in wholesaling, retailing, and industrial manufacturing.
- As it did in many other places, the Great Depression of the 1930's virtually eliminated the regional capital base. Many companies were sold or moved away. The second World War led to the revitalization of the shipyards; however, in 1954, the shipyards moved their entire operation to Collingwood and this had a significant impact on the local economy. Nevertheless, gradual and continued diversification in all sectors brought the Town's population to 11,000 by 1972.
- A range of companies have set-up shop in Midland over the years, including: TRW, ELCAN, Kindred, Weber Tool, Baytech Plastics, Pillsbury, NEBS, and more. In 1993, the Financial Times newspaper referred to Midland as a "high-tech super town". ELCAN, now part of the American-based Raytheon Corporation, is the largest employer in Midland with over 900 employees.
- The North Simcoe Sports and Recreation Centre (NSSRC) opened in 2005 and has been a popular place for sporting events, conventions and trade shows, receptions, concerts, and more.
- The Midland Public Library, located in the heart of downtown, underwent a multi-million dollar expansion that was completed in the Spring of 2010. There is now increased space for meetings, programs, and improved accessibility.
- Midland Cultural Centre (MCC) is currently in construction and expected to open in Spring 2012. The MCC will be a year-round facility for arts and culture designed to attract and serve local members, residents, and visitors to the area. The MCC will house art galleries, classrooms, theatre, and an event centre.
- Throughout the changes that Midland has witnessed, the Town continues to flourish economically with industrial expansions, commercial growth, tourism, and a good balance of residential development. Midland truly lives up to its motto: Persequi qualitatem vitae, meaning "in pursuit of quality of life."