There are two Captaincies per year (3 times before 1985). The winner of the Heavy Tournament becomes Captain, and whom he/she fights fights for becomes Heart.  Upon Stepping down as Captain and Heart, the Captain is added to the Order of the Polar Bear, and the Heart to the Companion's of the Snowdrop.
Either the Fighter or Inspiration (or both) must be from the Barony to enter the tournament.  After AS LI, Captaincy is held annually in Spring, Commander is held Annually in Autumn.  After AS LVI, the Captaincy and Commander tourneys are held Annually in Autumn.  

Circlets worn by the current Captain and Heart of Winter's Gate

The Heart has additional regalia, a necklace

Circlets made by Violet and Elena in A.S. LI (2016)