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The Pup Cup

This is definitely not your ordinary talent contest.

"Border collies do it with a herd—vote for Kylie!" reads one sign held by a contestant's companion. A dreadlock-wigged entourage, save for one member in a blonde wig, accompanies a natural-blonde contestant who originates from the small island of Culebra off Puerto Rico. And a third competitor, about the same size as the tiny trophy he gets to take home just for participating, tries to bribe the judges by presenting them with a fresh lobster.


Folks vie for the best spot to watch the Pup Cup, held during the annual Maine Boats, Homes, and Harbors Show.

Welcome to the wonderful, wacky war for the Pup Cup, held during the annual Maine Boats, Homes, and Harbors Show, where chutzpah—or, to quote the emcee of the event, chutzpaw—reigns supreme.

Formally known as the World Championship Boatyard Dog Trials, the competition attracts the attention of marina and yard dogs (and their humans, of course) from all over the country. While only six entrants make it through to the trials—which include a dockside obstacle course, dinghy-hopping challenge, and freestyle event—their furry finesse makes it a not-to-be-missed occasion.

And then there are the rules, which have a decided twist. Try these on for size:

1. Either the dog or handler must finish completely soaked.
2. Cheating is not only tolerated, but encouraged.
3. There are no other rules.

Zeke Chesley, a yellow lab from Contoocook, New Hampshire, seems to take rule number one to heart. In the process of diving into the water to retrieve a lobster buoy during his freestyle event, he nearly flips his human out of the canoe they're both sitting in (which he'd just "transformed" into an outrigger canoe by hanging his tail over the side). By contrast, even if Tyler MacMillan, a Chihuahua from the show's host town of Rockland, Maine, secretly considers soaking his human, there's no way he can do it—not even if he tries to gain weight by swallowing the lobsters he loves to trap. After all, he weighs just eight pounds, four ounces. As for the dinghy-hopping challenge, he and his owner have no choice but to cheat: She lifts him up out of the boat so that his tiny legs can reach the edge of the dock.

The crowd goes particularly wild for two competitors, Soldado Woollette, a Culebrense from South Thomaston, Maine, and Kylie Davis, a border collie from Rockland. Soldado dazzles them all by walking on water—well, sort of. Her freestyle event involves racing across a set of lobster crates spaced out from the dock to a rowboat in which her human sits. Soldado does it with ease, additionally jumping through a hoop while on the dock and then climbing a folding ladder before leaping onto her human's back. The judges are as wowed as the crowd: All three hold up placards with nine paws each (out of a maximum of ten). They do the same for Kylie after she catches three lobsters (in reality, stuffed toys her human tosses to her) and drops them in a pot to "cook" them—though she plays long enough with the last one to make the emcee quip, "Kylie's waiting for the melted butter." She finishes her feat by pawing a giant Staples "Easy" button. The tiebreaker goes to Soldado, based on the crowd's applause, and the natural-blonde contestant from Culebra wins the coveted Pup Cup.

The rest of the competitors don't go home empty-pawed, however. Each receives a bone-shape trophy (which thankfully none gets the urge to gnaw on) and, based on their fervent barking, vow to return the following year to be crowned champion.

Let's hope these furry contestants' bark is worse than their bite.

Editor's note: This year's championship trials will be held the weekend of August 10 to 12. For entry information and details about the boat show, visit World Championship Boatyard Dog Trials.

This article originally appeared in the May 2007 issue of Power & Motoryacht magazine.