Plymouth was first settled in 1825, incorporated as a village in 1867 and became a city in 1932.

The first settlers to come to what is now known as Plymouth, Michigan, were Keziah (Benjamin) and William Starkweather. Farmers from Preston, Connecticut, they purchased 240 acres of land from the United States government on March 11, 1825, for $1.25 per acre. The Starkweather clan had lived in Preston at least as early as 1694, according to records of a land gift in which Captain John Masons gave land to Robert Starkweather, William's grandfather. William, ninth born of 11 siblings, and his wife Keziah brought their firstborn son Albert to the area and built the first home in Plymouth, at what is now the southwest corner of Main Street and Ann Arbor Trail. The first home was a lean-to, and was later replaced by a log cabin, which has since been lost to time. William's eldest son Albert died at age 20 while attending the newly formed University of Michigan as a sophomore. George Anson Starkweather, William's second-born, was the first non-native American born within the boundaries of what is now known as the city of Plymouth. His father William died at 44 years of age, from typhoid fever, and his mother Keziah two years later, leaving their eldest son George at 20 years of age. William and Keziah's home in Old Village (circa 1835) is located at 557 North Mill Street.

The history section of the City of Plymouth website indicates that The City of Plymouth was settled by Luther Lincoln on April 2, 1825, though according to the United States Department of the interior – Bureau of Land Management, in a letter from Mr William H. Richards, Director and Chief, Branch of Surveys, in his letter to Karl Starkweather dated April 29, 1954, he states that upon inspection of the tract books held by the Bureau: "Of interest to you personally are the notations of the CASH entries Nos. 1195, 1199, 2991, and 3241 of William Starkweather, for SW1/4 sec. 26, E1/2SE1/4, sec. 27 E1/2NW1/4 sec. 25, E1/2SW1/4 sec. 34 respectively on March 11, 1825, March 14, 1825, April 29, 1829 and February 15, 1830." The two 1825 parcels that Starkweather purchased from the federal Government totaled 240 acres (0.97 km2).

Luther Lincoln, on the other hand, was granted two land patents by the federal government in 1825. One was in town 1 south, range 8 east, for an 80-acre (320,000 m2) parcel – the north east quarter of the Western half of section 33, and an additional 80-acre (320,000 m2) parcel in Town 1 South, Range 9 east, which is roughly the core of the city of present day Wayne.

Lincoln's former 80-acre (320,000 m2) parcel ranged both inside and outside of the present boundaries of the City of Plymouth. The land was roughly bounded on the west side by present day Mill Street, extended east to a border near or at the present Riverside park, on the north by the CSX Tracks, and on the south approximately by an east west line drawn at the point where Mill Street (Lilley road) intersects with Union street near where the entrance of Riverside Park is.

Regardless of when his land patent was granted, Lincoln built his place of business, his saw mill, and abode, near the eastern boundary of his land, along the Rouge River. His actual abode and saw mill was always outside the city limits. William Starkweathers home however, was at the very center of town, on the South West corner of Main and Ann Arbor Trail, at the exact site where Panera bread is today. Therefore, since Starkweather's home was always within city Limits, and since Lincoln's home and place of business, his saw mill, which was built along the Rouge River, were always outside the city limits of Plymouth, William, who brought his entire family with him and built a lean to at the Panera site as the first home, was the first settler within city limits.

In 1830, William purchased an 80-acre (320,000 m2) parcel of land on Plymouth Road, outside of the present Plymouth city limits, where the Unisys plant now stands. William and Keziah then sold their land in downtown Plymouth and in 1831 purchased an 80-acre (320,000 m2) parcel of land in what was then called "North Village" (now called "The Historic Old Village") from John Norris Jr, whom originally purchased the tract from the federal Government. Four years later, William sold this same tract of land in Old Village to his brother Erastus at over a 400 percent profit. Two years later, Erastus sold it back to his brother William at a profit.

In 1831, William then purchased an 80-acre (320,000 m2) parcel of land, now bordered by Joy Road, Baywood, Ann Arbor Road and Sheldon Roads. That same year he purchased an 80-acre (320,000 m2) parcel of Land in Nankin Township, in the area of present day Westland, in the approximate area of just north of the Warren and Hix Roads intersection bordered by the east side of Hix. He also jointly with David Rider purchased an 80-acre (320,000 m2) tract of Land in Livonia, on Plymouth Road, the land now occupied by the Ford Motor Company Livonia Transmission Plant. In 1844, William died. Two years later his wife Keziah died. The land in Old Village was then passed to William's son, George A Starkweather.

After his marriage to Lydia (Liddy) Amelia Heywood in 1861, George Anson Starkweather and R. G. Hall were partners in a general store facing Kellogg Park. The partnership dissolved in 1870, and George built a dry goods store on the southeast corner of Liberty Street and Oak Street (now Starkweather), which he operated until 1901. George's wife, Lydia Amelia Heywood, was the adopted daughter of Mary Davis, of Plymouth. Liddy, as she was known as a little girl, was born in Wayne, Michigan, and was adopted at age 4 by Mary Davis after both of her parents died of typhoid. Lydia Amelia Heywood was also known as Amelia Davis prior to marriage, as she took on the Davis family name.

George felt that the railroad coming to North Village would give it a commercial advantage over the Kellogg Park area. In the 1860s, he convinced the Detroit and Howell RailroadCompany to build through the town. The first actual construction on the entire (east-west) D & H line began in Plymouth on February 6, 1867, at a ceremony where a cherry wood tie was fashioned on the spot and laid on the center line of the road, at Shearers Cut. Work during the time of the D&H was never completed; the line was completed under a new company.

The Detroit and Howell Railroad was merged into the Detroit, Howell and Lansing Railroad, and later merged into the Detroit, Lansing and Lake Michigan Railroad. It was under the DL & LM RR that the line between Detroit and Lansing was opened for public use, in August 1871. At the end of 1876, after operating for only five years, the DL & LM went into receivership and was reorganized as the Detroit, Lansing and Northern Railroad. The DL&N was then merged into the Detroit, Grand Rapids and Western Rail Road, which was finally merged into the Pere Marquette Railway in January 1900. The PM was in 1947 merged into the C & O, which later became the Chessie System, and as of 1987, is now known as CSX. As of 2011, over Plymouth's 144-year history in Michigan railroading, the east-west line through Plymouth had been operated under nine different names.

The history section of the City of Plymouth, MI web site states that the railroad station in Plymouth, was built by the "Pere Marquette Railroad" in 1871. This is not entirely accurate. The "Pere Marquette Railroad", did not exist until 1899. Although the "Flint and Pere Marquette Railroad", was chartered in 1857, PM did not take over operations of the lines through plymouth, nor did it build anything along the lines, until during or after 1900, with the merger of three railroad lines – the "Flint and Pere Marquette", the "Detroit, Grand Rapids and Western", and the "Chicago and West Michigan" Railways.

The north-south rail line through Plymouth was built by the Holly, Wayne and Monroe Railway. After construction was complete, The Holly, Wayne and Monroe Railway merged into the Flint and Pere Marquette system, May 30, 1871. In 1900, both lines (north-south and east-west) that ran through Plymouth, came under ownership of the newly formed Pere Marquette railway as stated above.

The first ever steam locomotive that pulled into Plymouth, came from Wayne, Michigan on the north south line, on April 27, 1871, and was known as the Grand "Excursion" by rail. So at least on that day, the Holly, Wayne and Monroe Railway was in actual operation. The source for this first steam locomotive that came to Plymouth, comes from Celestia Young's diary entry of that date, in which she states, "A lovely showery day. I tried to see instead of working out of doors, Grand 'Excursion' to Plymouth by rail – this afternoon – Wayne Brass Band & Star Spangled-Banners." Celestia was the sister in law of Jehial Davis (Step Father to George Starkweather's wife Lydia Amelia), and was a close family friend of the Starkweather family, whom for a time was a housekeeper for George A Starkweather. Celestia was known as "Aunt Celestia", to the grand children of George, and was as a sister, to George Starkweather's wife Amelia.

Starkweather was responsible for cutting Oak Street North through his farm in order to reach his new store and the train station. After his death in 1907, Oak Street was renamed Starkweather in his honor. In addition to his other pursuits George Starkweather took an active civic role. He served as a member of the State Legislature in 1854, had several terms as Township Supervisor, 16 years as Justice of the Peace, and was Plymouth Village President in 1898.

George Starkweather's grandson, Karl Hillmer Starkweather (who changed his name from Karl Starkweather Hillmer), was a respected and lifelong Plymouth resident and local historian, and Ford Motor Company employee at the Wilcox Lake Tap Plant in which he was shop steward. He died on May 1, 1969. His father, Lewis Hillmer, also served as village president for a time. Notable streets in Plymouth are named after some Starkweather family members, including Blanche (after Blanche Starkweather, daughter of George Starkweather), Karmada (after the grandchildren of George Starkweather – Karl, Max and Davis), Davis – after Davis B Hillmer – youngest grandson of George Starkweather, Starkweather (formerly Oak Street), Amelia (after Lydia Amelia Heywood – Davis -Starkweather) – George Starkweather's wife, and Rose – after Rose Hillmer, eldest grand daughter of George Starkweather. Starkweather Elementary School was named after George Anson Starkweather of Plymouth, which was converted to an adult education center. It was the first elementary school built in Plymouth largely through the efforts of grandson Karl Starkweather, who promoted the need for a ward school in Plymouth to local residents. Karl's wife, Mary E Starkweather, and Karl's mother (George's daughter Mary K. Starkweather – Hillmer), were charter members of the Plymouth Historical Society.

Daisy Manufacturing Company, now Daisy Outdoor Products, started in 1882 in Plymouth as the Plymouth Iron Windmill Company. In 1886 Plymouth inventor Clarence Hamilton introduced a new idea to the windmill company. It was a combination of metal and wire, vaguely resembling a gun that could fire a lead ball using compressed air. Lewis Cass Hough, then president of the firm, gave it a try and, after his first shot, enthusiastically exclaimed, "Boy, that's a daisy!"

The name stuck, and the BB gun went into production as a premium item given to farmers when they purchased a windmill. The gun was such a huge success that Plymouth Iron Windmill soon began manufacturing the Daisy BB gun in place of windmills. On January 26, 1895, the company's board of directors officially voted to change the name to Daisy Manufacturing Company, Inc.

Much to the dismay of Plymouth residents, Daisy moved its corporate offices and manufacturing facilities from Plymouth to Rogers, Arkansas in 1958.

In 2009 Plymouth Township was named 28th Best Place to Live in the United States by CNN Money Magazine.