Winston is a lumberjack at the Burne Lumber Company, adoptive brother of Dood and Ford who first appeared in the Dragons: The Nine Realms episode "Downpour".
During one scene in "Downpour", Winston's skin tone is changed. This has been confirmed by John Tellegen to be an animation error due to the different lighting of the scene in a conversation with Audrie Greywind.
This later happens again in "Poison Control", "In Too Deep", and "Hobs and Saw" for very brief scenes.
Despite being different races Buzzsaw states that Ford, Winston and Dood are brothers so it's most likely the three are related through adoption.
Weapons: Inferno, Astrid Hofferson's Axe, Hiccup's Viking Helmet, Hiccup's Shield, The Mangler (Hiccup's Bola Catapult), Dragon Root Arrows, Toothless' Saddle and Tail Fin, Dragon Scale Armor, Deathgripper Venom
Plants: Dragon Root, Blue Oleanders, Purple Oleanders Other: Yak Nog, Bork's Papers, The Book of Dragons (original, The Nine Realms), Hiccup's Prosthetic Leg, Astrid's Betrothal Necklace, Gobber's Peg Leg