We spent Saturday, August 1 on Derby Wharf with our cameras, and the Salem Cardboard Boat Regatta delivered everything its name promises. The Great Salem Maritime Cardboard Boat Regatta ran from 1:00 to 3:00 p.m. as part of the opening-day festival for Salem Heritage Days 2026, the nine-day celebration of Salem’s 400th anniversary. More than two dozen hand-built cardboard boats hit Salem Harbor at Salem Maritime National Historical Park — pirate galleons, a rotary phone, a pink Barbie dreamboat, several very determined elephants, and tributes pulled straight from Salem history. Costumed crews paddled for glory while a seawall packed with spectators roared for every heat. Some boats crossed the finish line. Some became submarines. And yes, there is a Titanic Award for the most spectacular sinking. The whole thing was free, unhinged in the best way, and very, very Salem.
Costumed crew in tutus with their Nautical Nonsense cardboard boat at the Salem 400 Cardboard Regatta in Salem, MA – Photos by Creative Collective
What is the Salem Cardboard Boat Regatta?
The rules are simple and the physics are unforgiving. Teams build boats out of cardboard — cardboard and heroic quantities of duct tape — then paddle them across Salem Harbor off Derby Wharf. This year’s builds were themed around the American Revolution and other big moments in Salem’s history, in honor of the Salem 400+ quadricentennial. The race anchored the Heritage Days opening festival, which ran 11:00 a.m. to 6:00 p.m. at Salem Maritime National Historical Park with food trucks, a beer garden, historical demonstrators, and free deck tours of the tall ship Pride of Baltimore II. Meanwhile, safety was genuinely dialed in: a harbor patrol boat idled just off the course, and snorkel-equipped safety divers shadowed every heat. Watching was free. Sinking, apparently, was also free.
Boats built from 400 years of Salem history
Furthermore, these crews did their homework. The Jenny Slew — a bold red build whose crew carried justice-scale props — honors the Massachusetts woman who sued for her freedom in 1766 and won. The Quero recalls the Salem schooner that raced news of Lexington and Concord across the Atlantic in 1775. The Endicott Pear floated as a tribute to the oldest living cultivated fruit tree in America, planted around 1630. We also spotted a General Glover farmhouse, a pirate crew flying Betsy Ross’s flag, and a castle-shaped contender named Holy Ship. Alongside the history came pure joy: a rotary telephone, a Ken crew launching a pink Mojo Dojo boat, viking helmets, black cats, and enough elephants to start a circus. Every hull was hand-painted. Every crew was in character.
Crew of the Jenny Slew cardboard boat raising their paddles in celebration at the Salem 400 Cardboard Regatta – Photos by Creative Collective
Who won? Ask the Titanic Award
Honestly, we were too busy photographing the sinkings to track the standings. However, the awards table told the real story — including a tall gold trophy labeled the Titanic Award, reserved for the most spectacular sinking of the day. Competition for it was fierce. We watched crews cling to capsizing hulls, wade ashore grinning, and tread water beside their wreckage while holding the flag high. One paddler hoisted a salvaged mast overhead like a champion. Costumed judges in powdered wigs worked the shoreline with clipboards, taking it all exactly as seriously as it deserved. That’s the secret of a cardboard regatta: the boats that sink are the ones everyone remembers.
Swimmers holding a Betsy Ross flag beside their sunken cardboard boat in Salem Harbor – Photos by Creative Collective
What else happened at the Maritime Festival on August 1?
The regatta was the loudest hour of a full waterfront day. The Pride of Baltimore II — the reproduction Baltimore Clipper that sailed into Salem Harbor the day before — towered over the festival with free deck tours running all afternoon. Additionally, the published music lineup opened with the Sea Dogs at 1:00, and the harborfront rang with sea shanties between heats. Spectators stacked three deep along the seawall. Kids claimed the beach. Underwater photographers in wetsuits worked the race course with dome-port cameras, chasing angles the rest of us could only guess at. For a first-time festival-goer, the whole scene answered a question Salem has been asking all year: what does a 400th birthday actually look like? Apparently, it looks like a cardboard elephant passing a police boat.
Spectators lining the Salem Harbor seawall with a tall ship in the background at the Salem 400 Maritime Festival – Photos by Creative Collective
Heritage Days keeps going through August 9
Consequently, if you missed the regatta, you have not missed the party. Salem Heritage Days 2026 runs through Sunday, August 9, with concerts at the Salem Willows, the Ice Scream Bowl on Salem Common, and Salem’s first-ever Porchfest closing the week. Meanwhile, Beverly is celebrating its own 400th right across the water — their kids’ cardboard boat race hits Lynch Beach on August 9, followed by the Homecoming fireworks. Our Beverly Homecoming 2026 guide has the full rundown. And for the story of how this whole anniversary year got its start, check out Food at 400+, the culinary festival that brought Roger Conant’s 13th-generation descendant back to Salem in June.
We photographed the whole day — all 178 images are free to browse and download in the full gallery.
→ View the full Salem Cardboard Boat Regatta gallery on Pixieset
Photos: Creative Collective.
Frequently asked questions
When and where was the Salem Cardboard Boat Regatta 2026?
Saturday, August 1, 2026, from 1:00 to 3:00 p.m. in Salem Harbor off Derby Wharf, during the Salem Heritage Days opening festival at Salem Maritime National Historical Park. Watching was free and open to everyone.
What is the Titanic Award?
It’s the regatta’s trophy for the most spectacular sinking of the day. Cardboard boats are not famous for their durability, so the award is hotly contested — and sinking crews get some of the biggest cheers on the wharf.
What tall ship was at the Salem Maritime Festival?
The Pride of Baltimore II, a reproduction of the sharp-built Baltimore Clippers of the War of 1812 era. She arrived in Salem Harbor on July 31 and offered free deck tours during the festival weekend.
Where can I see all the regatta photos?
The complete 178-photo gallery by Creative Collective is free to browse and download on Pixieset.
About the author: John Andrews is Founder & President of Creative Collective, covering the makers, small businesses, and creative community across Essex County and the North Shore. He spent August 1 on Derby Wharf with a camera, cheering for every boat that sank.
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