PORTLAND, OREGON — For our Halloween collection with the Portland Winterhawks, a familiar horse returns to the ice with an unexpected rider. The Headless Horseman takes the saddle of the Portland Buckaroo, his cape sweeping behind him and a jack-o’-lantern raised overhead. The custom artwork brings together a piece of the city’s hockey history and one of Halloween’s most enduring characters.

That meeting sets the direction for the collection. The bucking horse and its skates retain the playful character of the Buckaroos mark, while the headless rider, hockey stick and pumpkin give it a darker turn. Carried through red-and-black embroidery, oversized back graphics and smaller stitched details, the combination gives this five-piece collection a character of its own.

The horse carries a history that reaches well beyond Halloween. From 1960 to 1974, the Buckaroos played at Veterans Memorial Coliseum, winning three Lester Patrick Cups and finishing with the league’s best record eight times. Their success helped establish the following that Portland hockey would continue to build on.

The Winterhawks have returned to that history over the years, including wearing Buckaroos uniforms in 2008 to honor the earlier club. For this collaboration, the skating horse provides a connection between those chapters. Its lowered head, kicked-out legs and curled skate boots remain recognizable beneath the new rider.

We built the collection around that connection, bringing the Horseman Buckaroo into our signature styles alongside Portland lettering and the Winterhawks’ current crest. Red, black and cream give the artwork different settings across the collection, from dark embroidery against a light base to fine red lines that let black fabric become part of the drawing.

The lettering carries some of that same character. Sweeping Portland script sits alongside bold Winterhawks wordmarks, while striped ribbing and rope details draw from familiar hockey and sportswear styling. The jack-o’-lantern also appears on its own, carrying a small piece of the larger illustration into the collection’s quieter details.

Together, the five pieces give the Buckaroos reference a new place in Portland’s hockey wardrobe. The history remains visible in the skating horse, while the Halloween artwork offers another way for fans to connect with it.

Explore the limited-edition Official League × Portland Winterhawks Headless Horseman Halloween Collection.