The hospital in Musquodoboit Harbour had been a dream envisioned by locals since the mid 1940s, an idea behind which P. H. Weary and the local branch of the Red Cross were a driving force. The hospital was first incorporated in 1945 and meetings were held to discuss its construction. The official turning of the sod took place on July 5, 1948 and on June 8, 1950 the facility opened its doors as a nine bed Red Cross outpost hospital. The hospital was initially to be called the War Memorial Hospital but the 1945 Act to Incorporate the War Memorial Hospital, Musquodoboit Harbour, NS was amended in 1946, changing the name to Twin Oaks War Memorial Hospital. It was agreed that the provincial division of the Red Cross Society would equip and operate the facility as an outpost hospital, in a building that would be provided and maintained by the Twin Oaks War Memorial Hospital Corporation. The Musquodoboit Harbour branch of the Canadian Red Cross Society would be responsible for appointing a committee to supervise the operation of the hospital. Local businessman P.H. Weary was heavily involved with the Musquodoboit Harbour Hospital Committee from the beginning and served as president of the Twin Oaks Hospital executive committee in its early years. He was succeeded as president by W. S. Dickie around 1958.

The hospital served communities from Porters Lake to Tangier and was jointly owned by those communities. Around 1958, the Red Cross withdrew its support from the hospital and it was sustained by the community until the hospital was able to apply for government funding the following year.

In 1958 Twin Oaks was still operating as the original nine-bed facility. However, in 1976 a new facility was opened, and in 1984 it was a twenty-five bed accredited hospital offering a limited but essential range of service including acute and long term care. Its range had increased to include a service area spanning from Bell Road in Lake Echo to East Ship Harbour and north as far as Meaghers Grant.

Today Twin Oaks operates as a fourteen-bed facility offering a variety of services including an acupuncture clinic, palliative and respite services, acute care, outpatient care, emergency services, meals on wheels, nutrition counselling, social services, physiotherapy, occupational therapy, laboratory services, diabetic, foot, and acupuncture clinics; and diagnostic imaging services. It also hosts a number of tenant services such as addiction services, home care Nova Scotia, and Nova Scotia hearing and speech therapy. Today the hospital is also affiliated with The Birches Home for Special Care, a residential facility for seniors.