Grade II winner Trail City was represented by his first winner when his son Pepper Trail won Sept. 10 at Del Mar. A homebred for Patricia Youngman, the colt won at 5 1/2 furlongs in 1:04.15. Winner of the 1996 Arlington Classic (gr. IIT), Trail City (Red Ransom--Willow Runner, by Alydar) stands at Pepper Oaks Farm near Santa Ynez, Calif.Stakes winner Classy Prospector's first winner came Sept. 10 at Hoosier Park when James and Vicki Riddle's Mr. Classy won at 5 1/2 furlongs in 1:07.63. The gelding was bred by Don and Dana Myers' Swifty Farms. Classy Prospector (Mr. Prospector--Fantastic Look by Green Dancer) stands at Swifty near Seymour, Ind.