Past Winners

Photo by: David Stotzer, Cape Ann Photography, Gloucester Schooner Festival

Photo by: David Stotzer, Cape Ann Photography

Past Winners of the Esperanto Cup

2015 ~ Columbia
2014 ~ American Eagle
2013 ~ American Eagle
2012 ~ American Eagle
2011 ~ Spirit of Bermuda
2010 ~ Spirit of Bermuda
2009 ~ American Eagle
2008 ~ Virginia
2007 ~ Virginia
2006 ~ American Eagle
2005 ~ American Eagle
2004 ~ American Eagle
2003 ~ American Eagle
2002 ~ Pride of Baltimore II
2001 ~ Ernestina
2000 ~ America
1999 ~ Pride of Baltimore II
1998 ~ American Eagle
1997 ~ American Eagle
1996 ~ Spirit of Massachusetts
1995 ~ Spirit of Massachusetts
1994 ~ Race Cancelled
1993 ~ Spirit of Massachusetts
1992 ~ Spirit of Massachusetts
1991 ~ Adventure
1990 ~ Spirit of Massachusetts
1989 ~ American Eagle
1988 ~ Adventure
1987 ~ Spirit of Massachusetts
1986 ~ Pilot

The first Gloucester Schooner Festival took place in June 1985 in the form of a “rendezvous” between the American and Nova Scotian Schooner Associations. About 40 small and medium schooners participated in three days of racing and international camaraderie, sparking such excitement in the port that a committee was formed to organize a race for small, medium, and large schooners to take place on Labor Day weekend in 1986.