This weekend the town of Frisco will host the 11th annual Timberline Cruiser Regatta, a yachting event that embodies the fun-loving spirit of Colorado’s laid-back mountain communities. Sponsored by New Belgium Brewing Company, the race is open to anyone with a sailboat who has the chutzpah to sail across Lake Dillon, whose 9,000-foot elevation and notoriously variable winds can create frisky conditions.

But it’s not just the stunning alpine scenery and unpredictable breezes that make this regatta so unusual. Instead of giving the awards to the fastest boats like a conventional sailing competition, the organizers offer bonus points for all kinds of quirky deeds, such as donning colorful costumes, mastering games like hitting floating targets while speeding across the lake, and finding and singing to a (brave) volunteer mermaid, who is sometimes unwittingly exposed to “full moons” and “flashing beacons.”

The organizers take pride in coordinating what they consider to be an “anti-yacht club” race. “This event is unique because it takes the stuffy out of sailboat racing,” says Tom Hogeman, general manager of the Frisco Bay Marina, “and it has been supported in this noble endeavor by an iconic Colorado brand, New Belgium Brewing Company.”

In addition to the headlining race, the Timberline Cruiser Regatta features live entertainment, great local food, a live auction to benefit the Dillon Yacht Club Junior Sailing program, ice-cold beer, and—above all—a great time. “The race really embodies what a laid-back mountain town does to anything that seems to require a formal or stuffy attitude,” says Hogeman. “They make it wacky, dig out some costumes, drink good beer, and still manage to be really good sailors.”

Regatta participants get extra points for finding and singing to a mermaid. Credit: Todd Powell

If you go: The cost to register is $35 per boat (including up to four crew members). Registration will be held at the Frisco Bay Marina on June 22 from 5:30–7 p.m., and June 23 from 9–10 a.m.

Terri Cook
Terri Cook
Terri Cook is an award-winning freelance writer based in Boulder. More of her work can be found at