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

1986

1987

1988

1989

1990

1991

1992

1993

1994

1995

1996

Pilot

Spirit of Massachusetts

Adventure

American Eagle

Spirit of Massachusetts

Adventure

Spirit of Massachusetts

Spirit of Massachusetts

Race Cancelled

Spirit of Massachusetts

Spirit of Massachusetts

1997

1998

1999

2000

2001

2002

2003

2004

2005

2006

2007

American Eagle

American Eagle

Pride of Baltimore II

America

Ernestina

Pride of Baltimore II

American Eagle

American Eagle

American Eagle

American Eagle

Virginia

2008

2009

2010

2011

2012

2013

Virginia

American Eagle

Spirit of Bermuda

Spirit of Bermuda

American Eagle

American Eagle

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.