For many sailors, the phrase “dinghy race” conjures up images of highly structured, performance-oriented regattas for competitors ranging from junior yacht club youngsters in Optis up through Olympians in Lasers, 470s and Finns. Some dinghy racers take the sport very seriously and the stakes can be high.

But that’s not the kind of dinghy race that will happen off Flying Point in Freeport on July 10. The Cupcake Cup will emphasize fun over speed and sailing performance. The stakes are low, if there are any stakes at all. The idea is for people to have a good time.

The Cupcake Cup is as unofficial and informal as its host, the Flying Point Yacht Club. Both are the brainchild of Jonathan Handelman, a local resident and owner of the sailing sloop Cupcake and her tender, a Dyer sailing dinghy named Scofflaw.

“The Cupcake Cup started in 2002 as an impromptu race between friends from Mere Point to Eagle Island,” said Handelman. “Since Cupcake won that first race, we decided to follow the format of the America’s Cup and name the annual race for the first winner.”

In 2007, the Cupcake Cup became a dinghy race with a postrace party, held annually on the first Saturday following the Fourth of July weekend. The dinghy fleet grew to six last year, and Handelman said he would love to see more people participate.

“The Cupcake Cup is open to any kind of sailing dinghy that reflects the spirit of the event,” said Handelman. “We’ve had people race dinghies like Dyers, Fatty Knees, and a Cape Cod Frosty, and we’re hoping for a couple of Grub Tubs this year.”

In other words, think cute, small, fun dinghies.

The Cupcake Cup epitomizes all that is good about sailing small boats. Some of the best sailors in the world learned in small boats, and there is no better way to learn how a boat responds to the wind, wave action and the movement of its rudder than by sailing a dinghy.

The event is intended to be very, very low-key, and that is reflected in the slightly official, slightly whimsical Notice of Race (NOR). The few rules that exist are meant to keep things casual. Oar locks are required, motors are not allowed, go-fast racing dinghies like Lasers need not apply, and tricky interpretations of racing rules will not be tolerated. Each dinghy must have a crew of at least two; anyone short on crew can probably find a spectator willing to hitch a ride.

Participants will gather on a beach off Maquoit Road in Freeport at 11 a.m. They’ll race a typical windward-leeward course that will be “set at the whim of the Race Committee probably only a few minutes before the start.” The NOR also encourages racers to “Keep your fingers crossed for wind. But not too much. Or too little.”

The winner of the Cupcake Cup gets immortalized by having their boat’s name engraved on the Cup. They can’t keep the cup; it will remain on display at the host club headquarters (Handelman’s home). But according to the NOR, the winner will be permitted to hold the cup, “but only if they wash their hands first.”

Anyone interested in participating should send an e-mail to [email protected] so the organizers can arrange for the appropriate amount of food and beverages.

Gail Rice of Freeport and her husband, Randy, sail on Casco Bay. Contact her at:

[email protected]