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.
Picture of structures on the island
Picture of a wintery seminarian camp. 5 buildings are visible
Recovered by Frank Flemming as a child in 1978 when he mistook it for a softball and nearly broke his foot
Clifford Jenks attempted to bring his car to Raccoon while he owned it, but it got stuck. Jenks was forced to tie empty barrels to the vehicle and float it the rest of the way with the tides.
There is a flag pole standing on the eastern tip of the island in memory of Bill Dunn Jr. You might spot the chair next to it inviting him back home to his family.
A small pine was once decorated as a christmas tree in memory of Val Jackson's passing.
The island has been documented to being burned to cinders multiple times. the first occurrencence was in the mid 1900s, suspected to be the delinquents held in the seminarian camp that was destroyed in the flames. Another time when it was struck by lightning, and a final time in the past few years when someone attempted to clear the wooden debris on the island and ended up setting the entire island on fire for 2 whole weeks before the flames went out.