Row, row, row your boat to the 2025 Maritime Festival

Looking to indulge your inner sailor this weekend? Look no further than Greenport’s 35th Maritime Festival Sept. 20 and 21 for the fun-filled Merry Merfolk Parade, maritime vendors galore and more.

Attendees can enjoy the street fair, local food, live music, kids’ games, classic and ice boat exhibits, kayak races and more throughout the weekend’s 10 a.m. to 5 p.m. festivities. Folks can even test out their pipes singing along to sea shanties Saturday and Sunday starting at 1 p.m. with Ethel’s Mermen and Fiddler’s Green, respectively. 

The Greenport tradition, hosted by East End Seaport Museum and Marine Foundation, typically draws roughly 10,000 attendees each year. Newly minted executive director Erin Kimmel shared her excitement for this year’s Maritime Festival with The Suffolk Times. 

“[The festival] celebrates and preserves the maritime traditions that helped shape Greenport and, more broadly, the East End,” Ms. Kimmel said. She added that it turns history into a living shared experience and keeps local heritage alive.

2025 marks the third year of a beloved new tradition — the cardboard regatta. Competitors set sail Sunday, Sept. 21, at 1 p.m., racing from Mitchell Park Beach to the end of the marina pier and back. This year’s event is sponsored by Greenport Harbor Brewing Co., and Ms. Kimmel said it’s her favorite activity at the festival. 

The tradition blends creativity, teamwork and local spirit — and it doesn’t take a big budget. At least 15 boats will likely compete in the race, with registered boats named Bad Buoy, the Box Jelly, Fantasea and Dragon Riders already on the books. 

Think you have what it takes? Ms. Kimmel advises anyone interested in competing in the regatta to start building now because the competition is stiff. Register and find rules for the race at eastendseaport.org/cardboardboatregatta. Winners will be announced Sunday, Sept. 21, at 3 p.m. at Mitchell Park Stage. 

The annual Merry Merfolk Parade will be led by grand marshal Paul Kreiling at 11 a.m. Saturday, Sept. 20. Mr. Kreiling is a Greenport local who has spent the last eight years improving Third Street’s East End Seaport Museum as its curator. During that time, Mr. Kreiling reimagined exhibit spaces to vibrant storytelling exhibits of the East End’s historic maritime past. 

He’s known as a “jack of all trades” — a sailor, rigging specialist, painter, designer, volunteer and community leader.

“As former chair of the board of trustees and long-serving volunteer curator, he transformed our exhibit spaces from dusty displays into dynamic, engaging experiences that bring the region’s seafaring history to life,” Ms. Kimmel said. “Paul’s life and work embody the spirit of the East End’s maritime heritage, and we are honored to celebrate his lasting impact by placing him at the helm of this year’s festivities.”

East End Seaport Museum and Marine Foundation board president Sarah Mill Sands also commended Mr. Kreiling for his dedication to the museum.

“In addition, Paul is an undying advocate for the museum’s role as steward of Long Beach Bar ‘Bug’ Light and its iconic position as a treasured community resource at the entry to Peconic Bay,” she said.

All are welcome to walk in the parade. To participate in the procession, contact volunteer coordinator Joe Corso at 516-885-9138.

Vendors this year include local makers and farmer’s market favorites like Maizeat, Greenport Jerky, Lavender by the Bay and Sag Harbor Honey. Likewise, nonprofits CAST, East End Classic Boat Society, New York Marine Rescue Center, Stirling Harbor Foundation and CI Bird Sanctuary will set up shop at the festival.

For more information, visit eastendseaport.org/about-the-festival or call 631-477-2100.

Maritime Festival full schedule:

• Saturday, Sept. 20:
  • 10 a.m.: Maritime Festival opens
  • 10 a.m. – 5 p.m.: Deck tours of classic boats
  • 10 a.m. – 5 p.m.: U.S. Coast Guard Tent – Maritime Demonstrations
  • 11 a.m.: Maritime Festival Parade
  • 11:45 a.m.: Blessing of the Waters at Claudio’s Pier
  • 12 p.m.: Merry Merfolk Judging Contest at Mitchell Park Stage
  • 1 p.m. Sea shanties with Ethel’s Mermen at Mitchell Park Stage
  • 2 p.m. – 5 p.m.: Performance by Bangers & Mash at Mitchell Park
  • 2 p.m. – 3 p.m.: Kayak race setup and registration at the waterfront
  • 2:30 p.m.: Storytime with Miss Nina at Mitchell Park
  • 3 p.m.: Kayak race at the waterfront
  • 5 p.m.: Festival ends
• Sunday, Sept. 21:
  • 10 a.m.: Maritime Festival opens
  • 10 a.m. – 5 p.m.: Deck tours of classic boats
  • 10 a.m. – 5 p.m.: U.S. Coast Guard Tent – Maritime Demonstrations
  • 10 a.m. – 1 p.m.: Paul Drum Pirate and Mermaid Breakfast
  • 10 a.m. – 11 a.m.: Cardboard regatta registration and check in at the waterfront
  • 12 p.m.: Cardboard regatta at the waterfront
  • 1 p.m. – 4 p.m.: Who Are Those Guys performance at Front Street and Main Street Stage
  • 1 p.m. – 5 p.m.: Sea shanties with Fiddler’s Green at Mitchell Park Stage
  • 1 p.m. – 3 p.m.: Snapper fishing contest, ages 8 and under, at commercial dock
  • 3 p.m.: Cardboard regatta winners announced at Mitchell Park Stage
  • 4 p.m.: Greenport Fire Department raffle in front of Colonial Drugs
  • 4:30 p.m.: Eastern Long Island Hospital “Dream Green” Raffle drawing at ELIH OpShop, 321 Main St.
  • 5 p.m.: Festival closes