Portland SchoonerFest & Regatta
June 21-24, 2019

Experience the Thrill of Tall Ship Racing! Support Education at Sea for Maine Teens!

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Portland SchoonerFest

Portland's own spring regatta for traditional sail, Portland SchoonerFest and Regatta kicks off the summer sailing season the solstice weekend of June every year featuring 7 large, traditional schooners racing and parading under sail together in Portland Harbor with passengers participating onboard and viewing from shore. The 2018 event featured some of the most famous schooners in the country including Gloucester's Schooner Adventure, the 131' Harvey Gamage of Portland, and Bailey Island's Schooner Alert. These classics are racing against hometown favorites Bagheera and Wendameen. And new in 2018 were the first race for Marine Maritime Museum's legendary Schooner Mary E. and Timberwind, an original Portland pilot schooner. Please join us onboard in 2019 as we expect another amazing experience. At this time, only group tickets are on sale. We take groups from 20 to 60. To reserve your group email us at

Event Schedule and Tickets

Friday, 6/21/19 - 3:30 to 5:30 p.m. Welcoming Parade under Sail

Friday , 6/21/19 - 5:30 p.m. Official welcome Ceremony (free, no tickets required)

Friday, 6/21/19 - 6 p.m. to 9 p.m. Friday Evening Cruise-in-Company

Saturday, 6/22/19 - 10:00 to 12:30 Dockside tours on schooners

Saturday, 6/22/19 - 1:00 to 3 pm - First Race

Saturday, 6/22/19 - 3:30 to 5:30 pm - Second Race

Saturday, 6/22/19 - 6:00 p.m. to 9 p.m. Saturday Evening Cruise-in-Company

Sunday, 6/23/19 - 10:00 to 1230 Dockside tours on schooners

Sunday, 6/23/19 - 1:00 to 3 pm - Third Race

Sunday, 6/23/19 - 3:30 to 5:30 pm - Fourth Race

Sunday, 6/23/19 - 6:00 p.m. to 9 p.m. Sunday Evening Cruise.

Monday, 6/24/19 - 10:00 a.m. to 4 p.m. Casco Bay Gaffers Race, Portland to Bailey Island, ME

Monday, 6/24/19 - 5:00 p.m. to 8 p.m. Casco Bay Gaffers Race Awards Party (free, no tickets required)

Tuesday, 6/25/19 - 9:30 a.m. to 3:30 p.m. Bailey Island to Boothbay Windjammers Race


Tall Ships Maine, a chapter of Tall Ships America, and the group responsible for the Tall Ships Portland 2015 festival, is a co-host for this event. Tall Ships Maine provides 1-week sail training opportunities with academic credit to high school students from all across Maine. It also hosts small and large tall ship events in Maine from time to time. Portland SchoonerFest is its first annual event.

Host Schooners

Host Schooners Wendameen & Bagheera, well known to local sailing fans, are both John Alden designed schooners and both built in East Boothbay, Maine in 1912 and 1924 respectively. These classics are the two oldest schooners in the fleet this year but are well known for their speed and comfort and are expected to be at the front of the fleet all weekend.


If you are looking to sail with a particular group of people, click on these links below to join them. If you would like to form your own group, email to set that up.

Schooner Adventure

Schooner Adventure

We are really excited to join the racing and spend the weekend in Portland,” said Stefan Edick, Captain of Schooner Adventure of Gloucester. “Portland’s sail training community is growing and we look forward to showing Adventure’s transom to the other fine schooners who will be there to see us. With our waterline of 107 feet and our overall length of 122, we should be very fast and spectacular in Portland Harbor.
— Edick, Captain of Schooner Adventure of Gloucester
Host schooners Bagheera and Wendameen

Host schooners Bagheera and Wendameen

You are welcome to Portland. We can’t wait to show you some local knowledge and not just on the race course!
— Michelle Thresher, President, Portland Schooner Company
Harvey Gamage

Harvey Gamage

I’m so pleased that the Harvey Gamage can support Tall Ships Portland. This effort is a great opportunity and we look forward to participating in SchoonerFest for years to come. There is an economic component that is very important for Portland.
— Phin Sprague, Owner of Harvey Gamage
Schooner Alert

Schooner Alert

Schooner Alert, designed by Paul Rollins with strong design influences from John Alden and Bud McIntosh and built by Paul Rollins in York, Maine was launched in 1992. She was built as yacht and shares part of her history as a commercial fishing schooner out of Portland. She is now based in Bailey Island, ME and is a US Coast Guard certified passenger vessel taking 28 passengers.