Richard Green Sr. began his trucking career in the 1940s by hauling cans of milk from local farms to creameries with his one truck. In 1950, he purchased a single axle tractor and a 30-foot cattle trailer to transport various goods, including cattle, hay, sawdust, and Christmas trees to Florida and oranges back to Vermont. In the 1970s, Richard's sons, Larry and Richard Jr., also started trucking with one truck each, hauling a variety of items, including fruit, produce, and windmills throughout the United States. In 1984, Richard, Larry, and Richard Jr. incorporated and renamed the business Richard I Green INC. Their contracts included hauling cream and milk from the St Albans Coop and ice cream from Ben & Jerry's. The business expanded rapidly, and by the late 1980s, it had grown to include 25 trucks and 30 employees. In 1989, the Green family built a new truck shop on their family farm, which remains in use today. Throughout the years, family members, including Richard's daughters, Becky Demar, Nancy Kane, and Sally Duffy, and their children, Carol Dunphy and Ann Green, have worked for the company in various capacities. Richard Jr. and Ann's son, Brian Green, began running the daily operations of the business in the mid-2000s.
Currently, Richard Green Trucking has expanded its operations in several directions. Richard Jr. and his wife, Liz Green, opened a truck school in Milton, Vermont, and their son, Alex Johnson, helps run the day-to-day operations. The company now specializes in hauling liquid chocolate products for companies like Barry Callebaut, Godiva, and Hershey. The business has expanded to the Midwest, with a hub in Robinson, Illinois. With the transition to the chocolate industry came the need for a food-grade wash facility, leading to the opening of their first Food Grade wash facility in Enosburg Falls, Vermont, in February 2016. In 2019, Brian's wife, Amanda Green, joined the team and manages the tank wash.
Together, Brian and Amanda have now opened their second tank wash, RIG Tank Wash, in Robinson, Illinois.