- "You will always be welcome here on the Island of Wingmaidens. Every one of you."
- ―Atali's warm welcome to the Dragon Riders[src]
- "An idyllic aerie in a remote corner of the archipelago, Wingmaiden Island serves as the flying females’ secret launching point — so secret, they’ll go to any lengths to protect it!
The Wingmaidens have long flocked to this secluded island, as it’s the hatching place of their beloved Razorwhips. Wearing the juvenile dragons like winged backpacks, these warrior women maintain their forested, tranquil preserve and eradicate any enemies that happen upon its shores. As all who would dare predate upon Razorwhips quickly learn, Valhalla hath no fury like a Wingmaiden scorned!"
- ―Hiccup's Journal
- "Amazing. Just amazing. The density of the vegetation is unparalleled for an island in this area of the..."
About a thousand years before the events of "Snotlout's Angels", Razorwhips nearly went extinct because male Razorwhips continually killed the offspring of rival dragons. So the Wingmaidens vowed to help the species out, offering to care for the hatchlings on their island and help defend them from any male presence. The dragons then made the island their home, including their nesting grounds. It's revealed that Windshear was once one of the Razorwhips they had cared for before Heather found her.
In the episode, "Snotlout's Angels", Snotlout was brought to Wingmaiden Island after he fell into the sea and the Wingmaidens rescued him. While searching for him, Astrid, Ruff, and Heather are warmly taken in by the natives, where they are offered rest, a warm meal, and entertainment; specifically boar wrestling. The natives explain that they aid Razorwhip mothers care for their young and defend against males who might try to harm them. Because of this, there are no males allowed on the island for their own safety and the well being of the dragons.
Wingmaiden Island appears again in Season 6, starting with the episode, "Chain of Command". Hiccup and Snotlout journey to the island to pick up Atali to bring her to a meeting of allies on Caldera Cay. Atali's second in command, Minden, faces an internal struggle about her importance within the Wingmaidens. Meanwhile Dragon Flyers attack the island.