Portland Junior Yacht Club was founded June 11, 1922 as a method of ensuring membership at the club. Annual dues in 1922 were $5. For many years PJYC existed inside PYC's Portland Harbor location, which was crowded, dirty, and not conducive to sailing. When Portland Yacht Club moved out of Portland Harbor in 1947 to a cottage on Falmouth Foreside, PYC had easy access to what is still today one of the finest sailing venues on the East Coast. The PJYC Boating Program, now known as the Portland Yacht Club Junior Sailing Program, was born in 1950, begun by among others Hasket Derby, a PYC member who was instrumental in bringing a fleet of 14 Turnabout Sailing Dinghies to PYC.

PYC Junior Sailing flourished for many seasons as a half day program, first in the old shed next to the club, and later in the 1970's moving to the new Junior Room upstairs at the club, a space the program still occupies to this day. During the mid 70's the program also retired the by now worn out Turnabout fleet and replaced it with a fleet of Widgeons, a sturdy 14' main-jib-and-spinnaker design made by O'Day. Program enrollments during this time sometimes topped 150 students! A number of very influential people such as Tim Tolford and William Stanley, helped build the program into one of New England's finest.

Through the 1980’s, a design known as the Club 420 was becoming popular at many New England clubs. The Club 420 is a heavier version of the International 420, with a sturdier, less flexible mast. The Club 420 was designed specifically to withstand the rigors of heavy use with junior and college programs, an area in which the International 420 had always come up short. In the last 10 years the Club 420 has become the most widely used junior double handed racing dinghy in the United States. In 1987, the PYC Jr Committee, led by among others Leigh Palmer, Dave White, and Tim Tolford, decided to expand the program and start moving into the Club 420s from the boats the program had previously been using through the 50's, 60's and 70's, a succession of dinghies including Albacores, Turnabouts, International 420s, and Lasers, among other designs. In 1987 PYC Jr Sailing became a full-day program, with kids at all levels sailing 5 days a week, 7 hours a day, in a 9-week schedule split into 3 3-week sessions, a format that has helped PYC Junior Sailing to become one of the top programs in the nation.

Starting in 1989, PYC Jr Sailors began a strong run of results in Sears (US Youth Triple-Handed Championship) and Bemis (US Youth Double-Handed Championship) competitions that has seen PYC sailors compete at Nationals in one or other of the events a total of nine times in 13 years. PYC won the Sears Area A's in 1989, 1992, and 1993, and finished second in 2000; PYC won Bemis Area A's in 1991, 1995, 1996, 1997, and 2000, and finished second in 2001. No other Area A club came close to that performance in those two events during that time period. In 1997, the PYC team of Pete Levesque and Nichol Ernst won the Bemis Trophy, after having finished third in 1995 and 1996. Levesque/Ernst also won Buzzard's Bay Regatta, US Youth Championship (then known as JO Nationals), and Club 420 North Americans, all within a year. In 2000, PYC achieved a rare triple-feat: qualifying sailors for Sears, Bemis, and Smythe Area A Championships, a first. During this period, Portland became a well-respected pipeline to College Sailing, producing 2 All-American Skippers, 1 All-American Crew, and 1 Honorable mention All-American Skipper between 1998-2005.

In the early 1990’s, under the direction of first Geoff Phelps and later Tracy Brennan, PYC began moving the basic levels of the program away from the fleet of by then worn-out Widgeons into Optimists. Optimists are small, single-handed dinghies that had been popular in the US Southeast from many decades but only recently had begun to make an impact on a national scale in this country. The Optimist, with its small size and simple rigging, is a perfect design for basic sailing and introductory racing. In the last decade, the Optimist has become the primary junior training boat in the United States, and more than 185,000 Optimists are sailed internationally. Starting in the early 90’s, PYC Jr Sailing, helped along by the contributions of Peter Curtis and Scott Fox, began purchasing Optimists, and by 1997, had established a formal traveling PYC Jr Optimist Team. The last Widgeon was retired after the 1995 season.

By the 2003 Season, the PYC Optimist Race Team had established itself as one of the strongest in New England, easily the strongest in Area A, having qualified 7 sailors for US National Team Trials and placed 4 sailors on the US National Optimist Team who participated in events in Mexico, South America, and Europe. PYC sailors won every local event they entered in 2003, except for Optimist New England's, where a PYC sailor placed 2nd. PYC in 2003 hosted those USODA New England Championships, at East End Beach Park in Portland, and the event was a terrific success, drawing 247 competitors from over 20 US States and 5 Countries.

In 1997, PYC Junior Sailing, under Scott Fox, began hosting the annual Northeast Junior Championships, which in 2000 became the Northeast Junior Olympics. Between 2001-2004 the event rotated each year between Portland Yacht Club and Boothbay Harbor Yacht Club. Portland will be the host again in 2005, this time enlisting help from a number of local clubs such as Harraseeket YC in Freeport and Trefethen Evergreen Improvement Association on Peaks Island. In the 2004 version of Northeast JO's, hosted by PYC at East End Beach Park, 274 competitors in 204 Optis, 420s and Lasers competed in what has become one of the largest junior regattas in the country.

Scott Fox was also primarily responsible for taking a leading role in improving the safety of the program, and helped along by his guidance as well as that of PD's Geoff Phelps and Tracy Brennan, the program went from having three safety boats in 1991 to 10 in 1999, had an equal number of VHF radios, and had vastly improved safety procedures, equipment and training.