The Working Waterfront

Portland kicks off first Schoonerfest

Regatta scheduled June 24-26

Staff Writer
Posted 2017-05-30
Last Modified 2017-05-30

The group Tall Ships Portland has scheduled a sailing regatta for traditional craft for June 24-26.

Portland SchoonerFest and Regatta will feature five, large traditional schooners racing and parading under sail together in Portland Harbor with passengers participating onboard and spectators ashore.

Organized by Tall Ships Portland to benefit its high school sail training programs, the event will feature several of the most famous schooners in the country including:


  • the magnificent historic 120-foot Schooner Adventure from Gloucester
  • Portland’s reborn 131-foot Harvey Gamage
  • Bailey Island’s classy 71-foot Schooner Alert
  • Schooner Bagheera and Schooner Wendameen, both of Portland.


Tickets to ride aboard the schooners can be reserved for $42-$60 person. Viewing is also possible for free from Portland’s Eastern Promenade at Fort Allen Park.

Following the weekend of racing in Portland, the visiting schooners will depart Monday morning to join the first-annual Casco Bay Gaffers Race which starts in Portland and ends at Bailey Island that afternoon.

All gaff-rigged sailboats are welcome to join the inaugural gaffers race for free and enjoy a morning skippers meeting in Portland and an afternoon post-race celebration in Bailey Island. Non gaff-riggers will have their own start and their race entry fees will benefit Tall Ships Portland youth sail training programs.

On Tuesday, several of the schooners will depart for Windjammer Days in Boothbay Harbor. Tickets are available to sail on each leg of the trip to Boothbay Harbor.

Tall Ships Portland, the non-profit responsible for the Iberdrola USA Tall Ships Portland 2015 event, is organizing the event. Tall Ships Portland provides one-week sail training opportunities with academic credit to high school students from all across Maine, as well as hosting tall ships events in Portland. Portland SchoonerFest & Regatta is its first annual sailing event.

To reserve space on board one of the schooners in the regatta, parade or evening sunset cruises, go to

If you would like to arrange events or book a group of more than 10, please call 207-450-5363.