The area now known as Portland was settled in the early 1800’s, when it was found to be fertile farmland. In the mid-1800s the Louisville & Nashville Railroad Company began construction of a railroad line through the area to connect Nashville and Louisville, Kentucky. The first train depot was built and came to be called Richland Station.  The L & N train made its first stop at Richland Station on October 31, 1859; but because of confusion with another railroad stop named Richland in Grainger County, the small village of Richland Station was re-named Portland in 1888. Later on, businesses were established around the train depot, on Depot Street, the area now known as Main Street. Portland was incorporated as a city by the State of Tennessee in 1905; and the city limits now spans into both Sumner and Robertson counties.

Portland’s claim to fame as the “Strawberry Capitol” came about due to having many successful strawberry growers in the area, one from as far back as 1885, Along with multiple strawberry processing plants located in town, the Strawberry Crate Company that manufactured strawberry crates and quarts and employed up to 200 ‘hands’, supplying a half million crates per year. At one point, about 2,000 acres of strawberry crops were raised in and around Portland, with most shipped out by railcar.  In a peak year, a record of 115 rail cars shipped out in one day.  Locals report that during World War II, Portland strawberries were also air-shipped to England. 

In 1940 the annual celebration of strawberries began – advertised in the Upper Sumner Press as a “Celebration to Open the Berry Harvest”. Tennessee Governor Prentice Cooper was on hand, as well as mayors from surrounding towns and newspapermen from Nashville.   Now called “Middle Tennessee Strawberry Festival”, it is the longest-running festival in Sumner County, with various activities that go on for days prior to parade day on Saturday. In 2021, the City celebrated its 80th annual Strawberry Festival with Tennessee Governor Bill Lee walking in the parade.

Today, Portland has become an industrial powerhouse in the region with millions of square feet under roof, employing thousands of employees across multiple industries. Tennessee recently built a new exit (#121) on Interstate 65 at the Kentucky state line as part of the Hwy 109 corridor project through Portland that began at I-40.