What's Happening?
The Steamship Authority (SSA) has announced the winners of its 11th annual “Sail into Imagination” art contest. Four students from Vineyard schools are among those whose artwork will be featured in the SSA's 2027 calendar. The contest, which received
over 100 submissions, challenged students to create art inspired by the theme “the sea and me,” encouraging them to express their connections to the sea and the Steamship Authority. The selected Vineyard students include Rose Lopes (Oak Bluffs School, second grade), Boonraksa Montoya (Chilmark School, third grade), and Lillianna Grillo and Addison Seger (both West Tisbury fourth graders). Each of these 15 winners will receive a $100 SSA gift card. Additionally, Emily Wajkowski, another West Tisbury School student, won a $150 Visa gift card in a grand prize drawing for all entrants. The artwork was judged by Benton Jones, art director at the Cape Cod Museum of Art.
Why It's Important?
This annual art contest highlights the importance of community engagement and fostering creativity among young people in the regions served by the Steamship Authority. By encouraging students to reflect on their relationship with the sea and the SSA, the initiative helps build a sense of local identity and connection to maritime heritage. The display of student artwork on SSA ferries and in calendars provides a platform for young artists to showcase their talent, potentially inspiring future generations to engage with the arts and their local environment. For the SSA, it serves as a public relations effort, strengthening its ties with the community and demonstrating its commitment beyond transportation services. The recognition and prizes also offer tangible encouragement for artistic pursuits among students, contributing to their personal development and community pride.
What's Next?
The 2027 Steamship Authority calendars featuring the winning artwork will be available for pickup at SSA terminals starting in November. Posters of the winning art pieces will also be displayed aboard SSA ferries, allowing a wider audience to appreciate the students' creativity. The SSA will likely continue its annual art contest in subsequent years, building on the success and community participation seen in this year's event. This ongoing initiative will continue to provide opportunities for students to express their artistic talents and connect with the maritime themes central to the region. The online gallery of all winning art will remain accessible, offering a digital showcase for the students' achievements.
Beyond the Headlines
The “Sail into Imagination” contest subtly reinforces the cultural and economic significance of the Steamship Authority in the lives of island and coastal communities. Beyond its functional role as a transportation provider, the SSA acts as a cultural touchstone, influencing local identity and community activities. The contest encourages a deeper appreciation for the marine environment and the role of maritime transport in daily life, fostering a sense of stewardship among younger generations. This initiative also underscores the value of public-private partnerships in supporting arts education and community development, demonstrating how a transportation entity can contribute to the cultural fabric of its service areas. It highlights the broader impact of local institutions in shaping community values and artistic expression.













