2016 – 40th and final Great Dock Canoe Race held each year since 1977.
Naples Bay came alive with color, sound, and tradition during the 2016 Great Dock Canoe Race, transforming the waterway behind The Dock at Crayton Cove into a floating festival of community spirit. Spectators packed the Naples City Dock and surrounding piers shoulder‑to‑shoulder, leaning over railings and dangling their feet above the water as canoes shot past beneath them. The bright Florida sun lit up the scene—umbrellas, hats, and banners framed a crowd that ranged from longtime locals to first‑time visitors, all drawn to witness what was billed as the “Last Dance” for this beloved Naples event.
Launched in 1977, the Great Dock Canoe Race began as a quirky neighborhood challenge conceived by The Dock Restaurant and nearby boaters, but it quickly grew into one of Naples’ most iconic annual traditions. Over four decades, the race evolved from a friendly contest into a full‑scale community celebration featuring themed canoes, charitable fundraising, and a kind of organized chaos that could only happen on the water. By 2016, the 40th and final running carried a strong sense of nostalgia; for many families, the race had literally spanned generations of paddlers and spectators.
On race day in 2016, every inch of dock space was claimed early. Families with young children, longtime race veterans, and teams in matching shirts crowded the Naples City Dock entrance, using the sign as an unofficial meeting point before heading to their favorite viewing spots. Down on the water, support boats and committee craft orbited the course, radios crackling as officials coordinated heats and kept the traffic moving. The Dock Restaurant provided the atmospheric backdrop—its familiar roofline and waterfront decks framing the start and finish lines while waitstaff and patrons paused to cheer.
A towering balloon figure in full disco pose riding on a festooned canoe at the 2016 Great Dock Canoe Race
The real stars of the event, of course, were the paddlers. Some approached the day like a serious athletic challenge, digging hard into the chop as they sprinted past the banner that announced the 40th and final Great Dock Canoe Race. Other teams leaned into the event’s playful roots, decorating their boats with elaborate props and costumes. One of the most memorable entries featured a towering balloon figure in full disco pose riding on a festooned canoe, perfectly capturing the “Last Dance” theme and drawing smiles from the packed shoreline. The mix of genuine competition and tongue‑in‑cheek creativity gave the race its distinctive personality.
Amid the spectacle, the event remained deeply personal. Friends posed for photos still dripping with salt water after their heats, paddles in hand and smiles wide despite the heat. Families gathered in the shade of palms with toddlers perched on shoulders, colorful beads around their necks as they watched the action together. Veterans of past races stood side‑by‑side, their commemorative T‑shirts telling the story of years spent returning to the same dock, the same view, and the same shared tradition on Naples Bay.
Kim Kelsey and teammate paddle on Naples Outfitters canoe number 211 during the 2016 Great Dock Canoe Race
By the end of the day, as the final canoes crossed the line and the crowd slowly thinned, it was clear that 2016 had been more than just another race—it was a farewell celebration for a piece of Naples history. The Great Dock Canoe Race left behind memories of sun‑splashed Saturdays, community camaraderie, and the joyful chaos of decorated canoes battling tide and time, forever tied to The Dock Restaurant and the waters of Naples Bay. Is it the end? We will soon see… Stay Tuned.
