Milton sailing boats are covered and tucked away on Gun Hill Road for the winter, even though winter has not arrived. Down the coast at St. George’s, Tabor, and Hotchkiss, sailors are still on the water in September and October. Plenty of people are out in only a bathing suit and life jacket, enjoying the last warm weeks of the year. Many schools offer programs that let sailors grow and develop students new to the sport, yet Milton’s boats remain tucked away because of money, staffing, and the logistics of getting a team to the dock.
Fall sailing offers the team more time on the water. On the competitive side, fall sailing is different from spring sailing. In spring, the Varsity Sailing team races, with three boats competing against another school’s three. In fall sailing, fleet racing takes place where each boat competes individually. Fleet racing develops speed, starts, and individual boat-handling skills.
Sailing captain Emmett Burghardt ’27 reflected on the value of a fall program: “I think it has its benefits to the sailing team. Fall focuses on different kinds of sailing, fleet-racing versus team-racing, just as cross-country and track are different kinds of running.” He added, “St. George’s and Tabor have been faster than us in spring regattas, and we have diminished our ability to compete with them. Between the extra time in the fall plus the longer practices during the season since those teams don’t have a commute to the docks, we practice half the time each day and half the season, so only 25% of the top teams in New England.”
“We don’t have the same kinds of sailors applying to Milton that we had six years ago, and I think a big part of that is fall sailing,” Head Sailing Coach Patrick Broome said. On the non-competitive side, as Broome and Burghardt shared, the warm water allows just a bathing suit and life-jacket, not all the needed gear for iceberg spring sailing, lowering the cost barriers for all students to access Milton’s sailing program.
While there has never been an official program in the fall, students informally practiced and competed as a Milton team until three years ago. Parents facilitated all the transportation. Students frequently practiced at various sailing centers on whatever boats were available, and no coach supported them on regatta day. Head of School Alixe Callen ’88 recalled a moment a few years ago when high winds at a regatta caused a “major safety issue,” and the Milton team was dependent on other schools’ coaches to help. The school barred the unofficial group at that time from attending regattas without coaches, thereby halting the program.
Although Milton has already invested in the dock and boats, a hypothetical fall program would still have substantial costs: coaches, transportation, and insurance. Callen believes these costs run into the tens of thousands of dollars. For other schools, as Callen reflects, “their programs are endowed,” as they are key programs for the schools. Callen reflected that she “can’t say yes to everything, and Milton’s overall offerings are much greater than at St. George’s and Tabor,” which have water right on campus.
Despite these obstacles, sailing team members remain hopeful that Milton may one day have a fall program. Sailing Captain Dylan Cafferty ’27 feels that the added program would give sailors valuable time on the water to improve speed, communication, and boat handling. He acknowledged that “it is a much more complex endeavor than simply taking the boats out of storage.” Milton would need to pay coaches for a second season, arrange transportation, coordinate with Marina Bay, and determine how the program fits within the other athletic offerings. Still, because many of the country’s best teams sail throughout the year, Cafferty “would be fully in support” of a fall program. Burghardt shared a different perspective: he feels that due to fall sailing’s low price barrier requiring only a “bathing suit and lifejacket,” the fall season would foster an inclusive environment allowing “everyone to be on the water.”