There is conclusive evidence of the island being used as a Native American summer campsite.

Before any colonial buildings stood on the island, it seems to have been used as a shooting target. Frank Flemming, a Hough's Neck resident, once found a cannon ball on the island in 1978, alluding to its use as target practice for boats exiting the Weymouth Harbor way back when.

Raccoon was owned in 1700s by an Edward Capin but not much is know about him or his activities on the island.

Raccoon has a rich history in the 1900s, with evidence of buildings on the island as early as 1913. Raccoon was purchased by Clifford Jenks in 1923. Jenks was known as the "Human Fly" for his high altitude stunts climbing skyscrapers. The island was then bought by Stigmatine priests in 1928, turned into a religious camp for delinquent boys. The camp was famous for its two large guard dogs keeping the boys in line. Supplies and food for the camp were acquired from the general store located on present day Rock Island Road. Locals report that there was a water main out to the island, hinting at running water in the camp. This camp was suspiciously burned to the ground, perhaps a consequence of holing up a bunch of troublemakers together.

In the late 1900s, Raccoon was privately owned by Reverend Gerald O'Leary who lived on the island and allegedly distilled rum. After his death, the island went on sale for $5,000, but went unsold.

Raccoon is now the property of the DCR under the Boston Harbor Islands Division; claimed as eminent domain.