In the early 1960's Melvin Woodward formed Woodward's Oil Limited to service the home heat delivery business in Happy Vally-Goose Bay. The Company expanded to include trucking and stevedoring services, as well as provide aircraft ground handling services for International Military forces and civilian users at Goose Bay airport under Woodward's Limited.

1973 saw the establishment of Coastal Shipping Limited to provide fuel deliveries to coastal Newfoundland and Labrador communities. The Company has since expanded to include service to the Canadian Arctic with the tankers Tuvaq, Dorsch, Mokami and Sybil W.

In 1976 the Company opened its first General Motors franchise in Goose Bay, Labrador Motors Limited. Since then it has opened franchises in Labrador City, Bay Roberts, St. Anthony, L'Anse Au Clair and Hawkes Bay. In 1994 Woodwards acquired the provincial franchise for National Car Rentals and Woodward Rent-A-Car was formed. In 1977 Woodward Auto Sales was established.

In 1998 Coastal Labrador Marine Services commenced operations to provide freight and passenger service to Goose Bay and Labrador Coastal Communities. In 2000 Labrador Marine Incorporated was formed to include CLMS and the MS Apollo began ferry service on the Strait of Belle Isle. The Sir Robert Bond services Cartwright and Goose Bay from Lewisporte and the Northern Ranger provides service to coastal Labrador communites. The Astron was aquired in 2004 to provide freight service.