In 1873, Lewis P. Thayer, a newspaper entrepreneur, purchased the plant and the small subscription list of the Green Mountain Herald, a newly established weekly paper in West Randolph, situated in east-central Vermont. With Edward D. Upham as the editor, Thayer expanded the paper's circulation to cover the White River Valley region, introducing editions for Chelsea and Bethel. A fire in April 1877 destroyed everything except the paper's account books, but Thayer quickly recovered. By the end of the month, Thayer had merged the Chelsea Post, the Vermont News (Bethel, Vermont), and the Herald under a new title, the Herald and News. In 1879, Upham acquired a stake in the paper, running it until 1881 when Thayer bought back his partner's share. Luther B. Johnson purchased the Herald and News and its affiliated weeklies from Thayer in 1894, continuing its regional focus and adding editions for Rochester and South Royalton.

John Drysdale, a newspaperman from Springfield, Mass., came to Randolph in the early 1940s and purchased the Herald from Johnson. Under Drysdale, the name changed from The Herald and News to The White River Valley Herald and he raised his family in and around the Herald offices on Pleasant Street. Under Drysdale, the Herald switched from lead type to offset printing, establishing a printing press on Weston Street and introducing photography to the newspaper. His wife, Eleanor Dickey Drysdale was his dedicated partner in the business, even penning an editorial column each week.

In 1972, the Drysdales' son, M.D. Drysdale took over the paper. He was just 26, but had graduated from Harvard and served under his grandfather at the Springfield Republican. A wordsmith, Drysdale brought a flair to the writing and reporting of the paper. In the mid-1990s, he shut down the printing press and contracted with a nearby daily paper to bring color to the Herald pages.

Following on his father's success, M.D. employed a strong core of photographers, including Gordon Harding, Jack Rowell, Kevin Eaton, David Barreda, and Bob Eddy. In 2000, Tim Calabro joined the Herald as a student photography intern. He grew into the newspaper business and in 2015, he purchased the Herald from Drysdale.