Winners announced of 6th annual Sail Into Imagination art contest

Posted: August 2, 2021

Falmouth, MA (August 2, 2021) -- The Woods Hole, Martha’s Vineyard and Nantucket Steamship Authority (SSA) is pleased to announce the winners of its Sixth Annual “Sail Into Imagination” art contest for students in grades Kindergarten through 12. The winning artwork will be showcased in a 2022 calendar, onboard SSA ferries, as well as displayed on the SSA’s website at

Each year, the Sail Into Imagination contest encourages students to use their imaginations and artistry to share their visions of traveling aboard SSA ferries to Cape and Islands ports and to inspire artistic interpretations of growing up by the sea. The contest is open to students from any town on Cape Cod, plus residents of Martha’s Vineyard, Nantucket, Fairhaven, or New Bedford. More than 150 entries were received this year.

New to this year’s contest, one teacher was selected at random to win a $100 gift card to a local art supply store of their choice. The winning teacher was Mrs. Raye from Barnstable United Elementary School.

“There are so many talented, young artists in our region and it’s exciting to see our waters and ports through their eyes,” said Kimberlee McHugh, the Steamship Authority’s marketing director. “As always, we are thankful to everyone who submitted an entry, and we are very excited to see this year’s winning artwork in our next calendar.”

A limited quantity of calendars will be available for pickup at Steamship Authority terminals
beginning November 30.

The Steamship Authority extends its sincere thanks to Laura M. Reckford, executive director of Falmouth Art Center, who assisted with the judging.

The complete list of 2021 calendar winners follows:


Wren Marie Robertson

Age 11 – Chilmark School, Martha’s Vineyard

“Island Bound”


Brady Lipper

Age 11 – Barnstable United Elementary, West Barnstable

“Sail Into Imagination”


Charlotte Cramer

Age 10 – Oak Bluffs School, Martha’s Vineyard

“Firey Sunset Over Vineyard Sound”


Violet Simon

Age 8 – Chilmark School, Martha’s Vineyard

“Evening Sail Of Wonder”


Olivia Loffredo

Age 9 – St. Pius X School, South Yarmouth

“Sail Into Imagination”


Yasmin Ferreira

Age 10 - Barnstable United Elementary, West Barnstable

“Sail Into Imagination”


Willie Bologna

Age 7 – Chilmark School, Martha’s Vineyard

“Sail Into Your Dreams”


Maybeline Brown

Age 10 – Chilmark School, Martha’s Vineyard

“Land Beyond The Bright Sea”


Anderson “A.J.” Cramer

Age 9 – Oak Bluffs Elementary School, Martha’s Vineyard

“Have A Whaley Good Time Aboard The Ferry”


Maisie Duffey

Age 8 – North Falmouth Elementary, Falmouth

“Martha’s Magical Mystical Tour”


Dylan Waldman

Age 10 – Chilmark School, Martha’s Vineyard

“Sailing Into Summer”


Nicole Goulet

Age 6 – St. Pius X School, South Yarmouth

“Sail Into Imagination”


Isabella Kowal

Age 11 – St. James–St. John School, New Bedford

“Homeward Bound”