Since 1987 the competition has been run, "to celebrate the lives of the special people whose contributions have made a lasting impression here at Sugar Mountain Resort," according to a press release.
The name was changed in 2002 to honor the memory of Trundy, the resort's director of operations from 1987 until 2000, who passed away from cancer in February 2002.
A retired two star general in the Marine Corps, Trundy is remembered for his hands-on approach to running Sugar.
"He liked to be around young people, activities and sports," said mountain rep Kim Jochl. "He was someone who liked to get things going…very goal and achievement oriented and he found that kind of environment at Sugar."
Since beginning to donate all-proceeds to the American Cancer Society in Trundy's memory, the event has raised almost $4000 through entry fees and donations. Last year's race alone netted $1,145 and saw 63 skiers vie for the cup.
In the past the competition has taken place on Sugar Slalom, the mountain's traditional slalom course. This year however, the course has been moved to Big Red, a wider and slightly flatter slope in an attempt to attract even more competitors.
Racers will take two runs down Big Red and the best combined time in each of the 13 categories – ranging from four and under to sixty and over – will be recognized.
The fastest male and female finisher overall will also get their names inscribed on the Sugar Cup which is displayed in the trophy case in the main lodge.
"We get a very diverse group of racers," concluded Jochl. "Everybody knew Dick and wants to be a part of it."
Registration for the event takes place from 7:30 to 8:30 a.m. Saturday, March 3 and competition begins at 9 a.m. Entry fee is $15 and participant lift tickets are $25.