The TALL SHIPS CHALLENGE® Race Series began in 2001 on the Great Lakes. Thirty vessels from six countries, and 1000 sail trainees and cadets participated in the races, sail training rallies and port festivals in seven US and Canadian ports.   Detroit and Windsor celebrated their 300th Anniversary; additional ports were Kingston and Port Colborne, Ontario; Cleveland, Ohio; and Bay City and Muskegon, Michigan.

The 2002 series was sailed on the Pacific Coast of North America:   Sixty vessels from seven countries participated in the series which included port festivals in Richmond, British Columbia; Seattle, Washington;
San Francisco and Los Angeles, California.   Races were sailed from the mouth of the Strait of Juan de Fuca to San Francisco and then on to Los Angeles.   More than 1200 sail trainees enjoyed the experience.

The 2003 series was again on the Great Lakes: Twenty-seven vessels from India, the Netherlands, the British Virgin Islands, the US and Canada participated. Port festivals were held in Cleveland and Toledo, Ohio as part of the Ohio Bicentennial; Chicago; Muskegon and Bay City, Michigan; and Sarnia, Ontario.   Four races were held between ports and more than 1000 trainees enjoyed the races and cruises aboard vessels in the fleet.   Millions of spectators came to the city waterfronts to see the vessels and talk with their crew/trainees to learn about life under sail and the opportunities to sail on ASTA member vessels.

The 2004 TALL SHIPS CHALLENGE ® Race Series brought vessels together from ten different countries: Belgium, Brazil, Canada, the Cook Islands, Mexico, Poland, Romania, the United Kingdom, the United States, and Uruguay. Across 2,300 nautical miles these traditional sailing vessels tested their crews in friendly competition.   The sailors aboard proudly displayed their ships to fascinated crowds in a dozen ports between race segments. Under blistering Florida sunshine and through impenetrable Nova Scotia fog, the ships' crews led their trainees in every aspect of running the vessels. Hand in hand with learning the ropes, the ships promoted team effort, responsibility, and personal development.

The 2005 TALL SHIPS CHALLENGE® Pacific Coast series took place in conjunction with seven US and Canadian ports on the Pacific Coast of North America. Nearly 60 traditionally-rigged sailing vessels from Canada, the US, Mexico, New Zealand, Russia and other countries took part, crewed by young people (either civilians or cadets) ages 13 - 25 engaged in sail training programs under the supervision of captains and professional crewmembers.

The 2006 TALL SHIPS CHALLENGE® Great Lakes series took place in conjunction with four US ports: Cleveland, OH, Bay City, MI, Green Bay, WI and Chicago, IL. More than twenty traditionally-rigged sailing vessels from Canada and the US took part.