Long before settlers moved into the Connecticut Western Reserve, Seneca Indians traversed the area. They used an Old Portage Trail, which crossed the southwest corner of the city, to go from Lake Erie to the Ohio River basin. Inhabitants of the township speak to imagine what the country looked like in the early years, as Christian Cackler, stated in his “Recollections of an Old Settler” book, he speaks of "three tribes of Indians inhabited this section of the country-the Seneca's, the Tawny's, and the Chapeway's."  In 1798, Titus Street received a deed for land in the township from the Connecticut Land Company. Streetsborough (as it was originally called) received its name from Titus Street. Street, originally from New Haven, Connecticut, held the original deed to the 15,279 acres that made up the township.

Streetsboro was the last township organized in the county (other than Garrettsville.) In 1800, it was made a portion of Hudson township; in 1806 it became a portion of Aurora, under whose convoy it sailed until 1821, when Aurora cut loose from it, and Mantua took it under its wing.

In 1821, extensive surveying of the land took place, by Streets' agents Ralph Cowles and Lemuel Punderson dividing the area into lots of 100 acres tracts which was sold for $2-$6 per acre. All large roads were planned at this time. Streetsboro is established, as original settler, Stephen Myers constructs a cabin establishing the very first settlement.

By 1825, the first framed house was erected by Daniel Johnson. Titus Street also donated 840 acres of his land for a turnpike from Cleveland to Wellsville. The turnpike was completed within 2 years by 1827 and followed much the main route.  That turnpike is now known as State Route 14. Land was also donated for a town square and cemetery. Street gave an acre of ground at each corner of the center for a public square and very large stone was placed in the center of the square to designate the exact center of the township. This stone is believed to be buried directly at the center of Route 14/Route 43.  He also donated two acres a short distance South of the center for a burial ground and gave $60 to have it and the public square cleared off.

The Oldest framed home, the Singletary House began construction in 1826 and was completed in 1828, by owner John Singletary. Originally located on the Northwest corner of town square, the home has had a variety of identities, including a tavern, a stagecoach stop on the turnpike, a post office, the township’s first telephone exchange, three different antique shops, and even a stop along the underground railroad as it stood on the square during the Civil War.  Both Singletary and wife passed away in this home and are buried in the old Streetsboro Cemetery on Rt 43.

In 1971, Closs Antiques sold his and home to the Red Barn fast food chain. The two-story home was doomed for demolition, until Mark Defer talked his father, Henry, into saving the city's oldest home. The house relocated to a hilltop overlooking the Old Defer Farm just off State Route 14, until 2006, when it was moved to accommodate a new shopping development. The fate was still undecided until Wal-Mart stores donated funds to the Streetsboro Heritage Foundation, to help put the historic Singletary House back on a foundation. The Singletary House is now located behind Tire Source and Wal-Mart and is the home of the Streetsboro Heritage Foundation Museum.

The year of 1826 was very busy, as the first school in Streetsboro Township was built at Johnson's Corners (corner of old State Route 14 and Aurora-Hudson Road). It was a slab school house in the Northwest Corner of the township, with only eight children in attendance. At age 18, Clarinda Case became the first school teacher.

By 1827, the Township of Streetsboro is officially organized. It was the last township in the county to do so.

The famous Old Methodist Church was designed and constructed in 1851 near the square. Many years later, the steeple was destroyed by a tornado in 1956. The church was moved and relocated to Hale Farm & Village (Bath, Ohio) in 1973 and has since been restored.

The primary industry in Streetsboro during the Late 1800's was dairying. This was done on local farms and by the mid-1890's,  the Streetsboro Creamery Company established and built its factory. It shipped a large portion of its milk to Cleveland. Along with Streetsboro's dairy industry, cheese factories were established throughout and by 1885 the township had five factories up and running. A main purchaser of Streetsboro's dairy was The Feeder Dam Factory, owned by C. R. Doolittle, which was located just over the Shalersville border. Many of the cheeses produced here were shipped to New York.

The residents of Streetsboro celebrated its 100-year Centennial in 1922 with a community photo that can be viewed at several locations including Streetsboro City Hall and The Streetsboro Heritage Foundation.

Major growth, many refer to as the “Housing Boom” occurred in Streetsboro with the opening of the Ohio Turnpike on October 1, 1955, with Exit 13 (now known as Exit 187) initially being the only interchange in Portage County. By 1957, with the growth of the automobile industry, Streetsboro experienced a population explosion. Proximity to the Akron and Cleveland areas, along with direct access to Interstate 80 (Ohio Turnpike), Interstate 480 and State Routes 303, 43 and 14, the location greatly contributed to the rapid growth of manufacturing, distribution, commercial and residential development in the past fifty years.

By 1968, voters decided to merge the township and the village to become one city consisting of 25 square miles. Streetsboro was primarily a farming community until 1970.

In 1972, the Streetsboro Sesquicentennial 150^th celebration took place as the Streetsboro committee added a few twists of their own. One unique feature, according to Fred Waage (Sesquicentennial Chairman), was a muzzle loading rifle shoot staged by the Charcoal Burners Club of Parma. "The Charcoal Burner shoot, dress and live in the early 18th century time period," said Waage. He estimated 100 to 150 Charcoal Burners from a 1-600-mile radius camped on the City property to take part in the shoot.

The Streetsboro Plaza shopping center was patrolled by Lions Club members garbed as Keystone Cops. They "arrested" anyone who wasn't dressed in old-fashioned costume, as well as men without beards and women who wore cosmetics. Violators were brought before a "kangaroo court" and socked with fines up to .25 cents, Wage warned. Instead of the traditional beauty contest; the Junior Mothers club held a Ms. Streetsboro competition open to women of the community. Girls under 18 entered by writing a 250-word essay describing the person who best represented their idea of womanhood. For the men, there was a beard growing contest judged in three categories, longest, most unusual and most original.

Other highlights of the Sesquicentennial celebration included: a water fight among Streetsboro, Hudson and Aurora fire departments at the plaza, a parade from the high school to Wise Elementary School and a 3,000-slice birthday cake was served at the plaza before the Welcome Wagon Square dance began. As part of the Sesquicentennial celebration, a 3-foot large concrete-looking cylinder time capsule was filled with historical items and records and buried on the NW corner of public square as Mayor Robert French, and Sesquicentennial Committee President Fred Waage presided over the burial. A small hand-written “treasure map” looking document was drawn up with the intent that the time capsule would be unearthed during the Bicentennial celebration in 2022.

Shady Lake Park was a small amusement park operated by the Humphrey Family in Streetsboro, Ohio. The park opened in 1978 and closed in 1982. Most of the rides at Shady Lake Park were relocated from Euclid Beach Park. Many of the rides from Shady Lake Park ended up at Old Indiana Fun Park, including the Euclid Beach Chief. The tall gate structure, resembling the one at Euclid Beach Park, remained standing until 2004. Today, the land along Route 14 is home to Shady Lake Apartments and an Aldi’s grocery store.