Cowboy Pooh

This festive pin, titled Cowboy Pooh, was released in 2006 as part of the Trick or Treat 2006 series at Walt Disney World. The design features the beloved Winnie the Pooh, who first appeared in A.A. Milne’s 1926 stories and later starred in the iconic 1966 film Winnie the Pooh and the Honey Tree, dressed in a cowboy hat and riding a rocking horse. The pin incorporates a Pin on Pin element, giving the rocking horse and the surrounding desert scene a dimensional, layered appearance that adds depth to the artwork. A jack-o'-lantern and a steer skull are featured prominently in the foreground, underscoring the Halloween theme. The background showcases a dark, glitter-filled sky that enhances the spooky, nighttime atmosphere of the holiday. Collectors highly value this piece due to the enduring popularity of Winnie the Pooh as a Disney icon. As a Limited Edition 2000 release, this pin represents a specific moment in Walt Disney World pin trading history. The intricate details and the thematic crossover between a classic character and a Western Halloween aesthetic make it a standout for fans of holiday-themed memorabilia. Its design captures the whimsy of the Hundred Acre Wood while embracing the seasonal spirit of Disney's park-exclusive releases.