Corpulus Vinius says that the reason the inn has such a curious name is because, when he was a child, he had a pet skeever that would wink at him, noting that skeevers used to be much smaller. Thus, he named the inn as such.
- Lisette, the bard here, will sometimes play the tune heard in shops in The Elder Scrolls II: Daggerfall.
- There is a Giant Club on a shelf; however, it cannot be taken.
- Brina Merilis and Horik Halfhand will be banished to the Winking Skeever if Dawnstar is given to the Imperial Legion during Season Unending and then taken back after The Battle for Fort Dunstad.