Current Photo Contest Entries

Picture of the sun setting on the bay Photo by Emily Weide of Dixfield, Maine

Homeward bound Photo by Michael Farrell of Austin, TEXAS

We rise by lifting others and sails 🙂 Photo by Catherine Dooley of Tulsa, Oklahoma

My wife Jacqueline as the skipper Photo by Ira Kalish of Los Angeles, CA

Scared to crash Photo by Katharine White of Middletown, Nj

Lovely day Photo by Phyllis Bruder of Berlin, MD

Worms-eye view of the main sail Photo by Ashley Fuchs of Annapolis, MD

Worms-eye view of the main sail Photo by Ashley Fuchs of Annapolis, MD

Sail away! Photo by Yolanda Cantwell of Hebron, IN

Boat Photo by Gary Somers of Ashburn, VA

Anniversary sunset cruise! Photo by Devin Thomas of Annapolis, MD

5/30/2026 - Chesapeake Bay Photo by Andrew March of Washington, DC

Sails in the wind…. Photo by Christine Lewis of Olympia, WA

Sunset 5/29/26 Photo by Herb Jackson of Washington, DC

Moonrise over the Chesapeake Photo by Matt DuMont of Baltimore, MD

Cruisin’ on the Woodwind II Photo by Matt DuMont of Baltimore, MD

Cheers!! Photo by Justin Gubtt of Baltimore, Maryland

A pair of Ospreys at sunset Photo by Alan Brudner of New York, NY

Enjoying the beautiful bay sailing on the Woodwind. Dolphin and osprey holding a fish was exciting! Photo by Michael Blumenstock of Bowie, Maryland

Flag Photo by Jen Stogsdill of Vienna, VA

Pure happiness as we take a sibling sail!❤️ Photo by Erika Houska of Wadsworth, Ohio

Took this as we were pulling back into the harbor. It was a calm night and a pink sky. Photo by Valerie Davis of Annapolis, Maryland

I took this when I went on a sunset sail. It was my first experience getting out on the bay! Photo by Valerie Davis of Annapolis, Maryland

Our wedding day! Photo by Michele russell of Raleigh, NC

Celebrating our wedding aboard the Woodwind II Photo by Michele Russell of Raleigh, NC

An awesome Sail on the Woodwind to my favorite Lighthouse, Thomas Point Shoal Lighthouse. 10/5/2025 Photo by David Sites of Riva, Maryland

A guest steers the boat. Photo by Jessica Allison of Severna Park, MD

Sunset Photo by Brittany Charity of Owings, Maryland

It was our very first time sailing together ⛵️ The crew was incredibly kind and helpful, letting us raise the sail ourselves and really experience it hands-on. With the clear blue sky and the cool breeze, it turned into an unforgettable day 💙 Photo by Ye seul Cho of Rockville, MD

Freighter on the bay Photo by Ross Heisman of Annapolis, MD

My eleven year old son enjoying steering the boat. Photo by Bryan Jones of Millsboro, Delaware

Boat! Photo by Emma Anderson of Pflugerville, TX

Say Cheese! Photo by Sue Johnson of Birmingham, AL

I like to take photos from unusual angles. This photo of the sail and the clouds speaks to me of the freedom of moving in quiet on the waters Photo by Sandra Miller of Lansdale, PA

Stitching on the sail on a beautiful fall day Photo by Sandra Miller of Lansdale, PA

Bay bridge Photo by Jill MacMillan of Arnold, Maryland

Pirates of Chesapeake 🏴‍☠️ Photo by Elizabeth Regan of PLEASANTON, CA

4 nurses reuniting in Annapolis Photo by Lucia Dallas of Beaverton, Oregon

CBB Photo by Karin Roseman of Greenville, DE

Between the Bridges Photo by John Bonanno of Wyomising, PA