Cape Ann High School Essay Contest

Presented by the Essex Historical Society and Shipbuilding Museum and regional cultural partners: Gloucester Writers Center, Manchester by the Sea Museum, Rockport Art Association & Museum

Cape Ann has always lived by the water. This essay contest invites high school students to explore that connection across all four communities.

Prompt
For generations, people on Cape Ann have built their lives around the water. Write about how the relationship between people and the ocean has shaped this place. How does that relationship continue today, and what responsibility does the next generation carry forward?

In your response, include specific examples from Essex, Manchester by the Sea, Gloucester, and Rockport, and consider how each reflects both shared and distinct histories.

Length

No more than 1000 words.

Prizes
$2000 in prizes

  • $500 for a student of Essex

  • $500 for a student of Manchester by the Sea

  • $500 for a student of Rockport 

  • $500 for a student of Gloucester

Eligibility
Open to high school students attending school on Cape Ann.

Timeline
Submissions open May 1, 2026
Deadline June 1, 2026
Judging June 1 through June 15, 2026

Judges
One representative from each Cape Ann community

  • KD Montgomery - Essex Historical Society and Shipbuilding Museum

  • Eric Parkison - Gloucester Writers Center

  • Matthew Swindell - Manchester by the Sea Museum

  • Kristin Czarnecki - Rockport Art Association and Museum

Score out of 100.

1. Connection to All Four Communities (25 points)
Clear, specific references to Essex, Manchester, Gloucester, and Rockport
Shows understanding of both shared and distinct identities

2. Understanding of Water and Place (20 points)
Demonstrates how the ocean has shaped culture, work, and daily life
Grounded in real examples, not generalizations

3. Historical Awareness (15 points)
Incorporates accurate historical context or references
Connects past to present in a meaningful way

4. Future Thinking and Responsibility (15 points)
Reflects on the role of the next generation
Engages with stewardship, culture, or community continuity

5. Originality and Voice (15 points)
Authentic perspective
Clear evidence of independent thought
Not formulaic or generic

6. Craft and Clarity (10 points)
Well organized
Clear writing
Strong structure and flow

Note on Authentic Work

Submissions should reflect the student’s own thinking and voice. Essays that feel overly generic, lack specificity, or do not align with the student’s level may be reviewed more closely. AI use is not permitted.