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The juniors at Chelsea, eager to emulate their fathers, sailed in what was available, or in any contrivance they could put together. Occasionally, informal sailing instruction was given, and, at one time, formal classes were conducted. In 1962, Dick Armstrong taught Saturday classes. The following year, a fiberglass Penguin was purchased through Club-member contributions for the junior program.
By 1970, the number and enthusiasm of the juniors had increased, and a group of Club members led by Dick Bailey combined their talents and energy to construct and outfit eight fiberglass "Chelsea Dinks." These have been most successfully used for training the novice juniors.
The Sunfish has been preferred by the more advanced juniors due to the nature and availability of the boat. In 1971, there were ten juniors competing for the Sailing Class Championship and twelve for the Junior Championship on Junior Race Day.
| CYC Junior Champion |
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| 1963 | Corky Ross | 1971 | Dave Pfirman | 1979 | Mark Stewart |
| 1964 | Carol Urey | 1972 | Billy Heaney | 1980 | Mark Stewart |
| 1965 | Carol Urey | 1973 | Ben Williams | 1981 | Mark Stewart |
| 1966 | Pete Larson | 1974 | Lois Williams | 1984 | Chris Best |
| 1967 | Carver A. Dumke | 1975 | Ben Williams | 1986 | Brad Schwark |
| 1968 | Dave Pfirman | 1976 | Lois Williams | 1987 | Ada Garber |
| 1969 | Billy Heaney | 1977 | Lois Williams | 1988 | Brian Tesar |
| 1970 | Bill Witkowski | 1978 | Lois Williams | 1989 | Brian Tesar |
| | | | 1993 | Amanda Thompson
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As time went by the Chelsea Dinks were retired from the junior sailing programs. Six of them became the basis the Chelsea Dink National, a yearly race open to all who enjoy the fun of sailing a cranky small boat.
In the early 1970s Frank Newman started an Explorer Post at Chelsea that emphasised seamanship. It operated for several years.
Meanwhile, the junior sailing program grew. Stephen Schwark and Peter Bonk led a popular program that they turned over to Michael Doyle. Moss Calhella joined Michael Doyle. During their time the program grew from three weeks to four. The junior sailors also initiated a money-raising brunch that takes place on Memorial Day morning. Peggy Kraft then took on the progtam and turned it over to Andrea and Neil Pollack in 1999.The 1999 four-week prgram has 42 junior sailors, 24 of whom are present during each session. This number is set by the requirement that there will be no more than six juniors for each counselor. There are five JY Club Trainers for the beginners and four JY15s and three 420s for those learning to race. The program was also given a 470 that is used for the racers.
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