The first-place overall winning photo
The first-place overall winning photo
Each year, the Maine Windjammer Association invites its passengers and shutterbugs to submit photos for its annual photo contest. Winners are chosen in a number of categories. Tracy Sheppard of Rockland, which is home to five Maine Windjammer Association boats, was this year’s first-prize overall winner. In fact, the Sheppard family scored high, with Sean Sheppard taking home an Honorable Mention in the Best Overall category, and a Captain’s Favorite Award from Noah and Jane Barnes of the schooner Stephen Taber. 

Tracy Sheppard was awarded a cruise of her choice in 2019. Second- and third-place overall winners received gift certificates toward 2019 cruises. All additional winners in the many other categories received gifts from the Maine Windjammer Association. The overall winners of the 2018 Maine Windjammer Association photo contest are:  

2018 Overall Winners

• 1st Place: Tracy Sheppard of Rockland, Maine, for “Parade of Sail”

• 2nd Place: Duane Hoffman of Huntsville, Alabama, for “Maine Scenery Aboard the Lewis R. French”

• 3rd Place: Mikael Carstanjen of Orleans, Massachusetts, for “Heritage in the Great Schooner Race”

• Honorable Mention: Sean Sheppard of Rockland, Maine, for “Parade of Schooners”

All the winning photos may be viewed on the fleet’s online photo gallery at

The Maine Windjammer Association offers 3- to 11-day sailing adventures. For more information, visit