Their origin was presumably in the territory of Ennetmoos in Nidwalden, where a toponym Wichried (Wychried, 46°57′11″N 8°20′24″E / 46.953°N 8.340°E / 46.953; 8.340) has survived into modern times.
The first recorded member of this family was the knight Rudolf von Winkelried, attested in a letter dated to the 1240s.
These later Winkelrieds may reflect their origin among the nobility by keeping a coat of arms (displaying a crescent in a triangle).
But a man called Erni Winkelried is recorded again on 29 September 1389 and on 13 March 1396, after the battle where he supposedly died a hero's death.
Yet another Arnold Winkelried is recorded in the second half of the 15th century, in connection of a lawsuit of November 1474 and as delegate of Nidwalden at the Swiss Diet on several occasions during 1476 to 1482.
On 13 September he was instigated by cardinal Schiner to engage in a skirmish with the French men-at-arms outside of Milano, thus causing the disastrous Battle of Marignano.
After this dispute had been settled to his satisfaction, he entered French service in 1518 and participated in the 1521 campaign in Picardy in the rank of captain.