The area that now makes up the Town of Cumberland was first settled by the English as early as 1635 and was incorporated (as North Yarmouth) in 1680 as the eighth town in Maine. Following the Revolutionary War settlers cleared the western section of the town and established the hamlet that was to become Cumberland Center. In 1820 the residents of the western section of North Yarmouth were granted the right to divide the town and the Town of Cumberland was incorporated on March 19, 1821.

Mainland Cumberland’s economy has traditionally included farming and shipbuilding, and throughout the 19^{th century was primarily extractive in nature. Key agricultural products from Cumberland farms included dairy, beef, apples, potatoes, hay and corn. At least two canneries supported agriculture in the late 19th century through the early 20th century. Poultry farming became a leading industry in town by 1900, and by 1904, the town had four large greenhouses producing flowers.}

Between 1848 and 1933 rail service was an important component of the economic activity within the town – delivering local products to market; providing dry goods, furniture and other items from the stores in Portland and beyond to the town’s residents; and transporting area residents to the cities for work and errands.

Many of the civic institutions in Cumberland got their start early in the town’s history. Churches were part of the town early with several churches established in the 18th century. Cumberland schools got their start in 1821 and Greely Institute, which became Greely High School in 1966, was dedicated in September 1868. The building that was in 1974 to become the Town Hall was built in Cumberland Center in 1914. The Prince Memorial Library opened in 1923. 

Between 1690 and 1715 the white settlers left the area because of conflict with the area’s native populace and when colonists returned to the area some of them constructed garrison houses for protection. In 1727, the town’s boundary with Falmouth was re-established, and one hundred home lots were created, sixty-four of which were to be drawn by lot for new settlers. Later land divisions resulted in the creation of lots of between one hundred and four hundred acres in size. The area that was to become the town of Cumberland was comprised primarily of the one hundred-acre lots in the southwestern corner of North Yarmouth.

Following the Revolutionary War settlers cleared the western section of the town and established the hamlet that was to become Cumberland Center. In 1820 the residents of the western section of North Yarmouth filed a petition with the newly established Maine Legislature seeking the division of the town in order to avoid "the necessity of extensive travel … to attend a town meeting, and perform the ordinary duties of a citizen."4 The Legislature granted the petition and Cumberland was incorporated on March 19, 1821.

The new town, with a population of 1,386, included twenty-two square miles on the mainland and eighteen offshore islands. On of those, Chebeague Island, is the largest island in Casco Bay, has traditionally been a fishing, lobstering and seagoing community and currently is one of only fifteen year-round island communities in Maine. Chebeague was granted its independence from the Town of Cumberland effective July 1, 2007.

Churches were part of the town early in its history. A Methodist meetinghouse on the Cumberland-Falmouth line – currently the Foreside Community Church - was the site of religious services as early as 1789, with the present building constructed in 1811. The Congregational Church in Cumberland Center was first established in 1794. The West Cumberland United Methodist Church was originally formed in 1800. The Tuttle Road United Methodist Church was built in 1882.

Inventory of Historic Resources Cumberland has a number of important historical resources from the 18^{th and 19th centuries. According to the town’s assessing data} there are 27 homes built before 1800 and 190 homes built between 1800 and 1900. This accounts for approximately 7% of the homes in the town.

The Cumberland Historical Society has identified 50 key historical sites along with 5 homes of architectural significance within the town. The locations of these sites are shown on the map on the following page. The map also identifies three additional historical sites of significance identified in other town reports.

Among the historical sites are four churches:
• Congregational Church (1831),
• Foreside Community Church (1811),
• West Cumberland Methodist Church (1848)
• United Methodist Church (1882).

There are two cemeteries listed:
• The Congregational Cemetery and
• The Universalist Cemetery (Morrison Hill).

There are two monuments on the map:
• The Merrill Memorial (1928) and
• The Centennial Plaque (1921).