🏴‍☠️ Eastport Pirate Festival 2025: New England’s Biggest 20th Anniversary Pirate Party!

By Gerry Caron | August 28, 2025

Prepare for the “Platinum Plunder”: 20 Years of Piracy on the Maine Coast

Ahoy, adventurers! Secure your tricorn hats and sharpen your cutlasses—the 20th Annual Eastport Pirate Festival is setting sail from September 4–7, 2025. Known as the largest pirate gathering in New England and the Maritimes, this year’s “Platinum Plunder” celebration marks two decades of swashbuckling mayhem in downtown Eastport, Maine.

For four legendary days, Water Street transforms into a 17th-century pirate haven. Whether you’re a seasoned buccaneer or a first-time landlubber, this mostly FREE festival offers an immersive escape into a world of fire, steel, and seafaring lore.

A Treasure Map of 2025 Festival Highlights

This year’s anniversary edition is bigger and bolder than ever, featuring fan favorites and exclusive 20th-anniversary events:

• The Black Pearl Ball (Saturday Night): The festival’s crown jewel—a formal pirate gala. Dust off your finest velvet and gold for a night of glitz, glam, and dancing. Tickets are limited and available through the Eastport Art Center.

• Ravenbane’s Firecraft Show: Prepare to be spellbound as Connecticut-based performance troupe Ravenbane’s Firecraft lights up the night with world-class pyro-dramatics and fire-spinning.

• The Great Pirate Parade & Float Contest: Join thousands of costumed revelers on Saturday. Build a themed float or march with your crew to compete for cold, hard “loot” prizes.

• Tortuga Encampment & Pirate Workshops: Step into history at the living history camp. Learn cutlass fighting, weaponry safety, and “Piracy 101” from seasoned seafaring reenactors.

• Live Music & Shanty Sessions: Enjoy the maritime melodies of Rockin’ Ron and a rotating lineup of local bands across the Waterfront Main Stage.

• The 2025 Flag Contest: Witness the unveiling of the “Platinum Plunder” flag, designed by local artists to commemorate 20 years of festival history.

2025 Festival Schedule at a Glance

• Thursday, Sept 4: Evening festivities kick off with pop-up tavern games at Horn Run Brewery and social gatherings.

• Friday, Sept 5 (10 AM – 9 PM): Family-friendly day featuring vendor markets, youth pirate pageants, and the opening of the Tortuga Encampment.

• Saturday, Sept 6 (10 AM – 11 PM): The “Big Day.” Includes the Seaplane Parade (in coordination with regional events), the Pirate Parade, and the evening Black Pearl Ball.

• Sunday, Sept 7 (8 AM – 4 PM): The final blast! Rum barrel races, scavenger hunt conclusions, and the grand fireworks finale over the harbor.

Traveler’s Logistics: Smooth Sailing to Eastport

• Location: Downtown Eastport, Water Street (America’s Easternmost City!).

• Admission: FREE for all ages.

• Parking: Free street parking is available, but fills quickly. Arrive early or utilize the volunteer-run shuttle services.

• Pro Tip: This is a cash-friendly event. While many vendors accept cards, having cash on hand for the “loot” bins and local artisans is highly recommended.

Where to Stay: For the full experience, stay in the heart of the action at Motel East, Todd House B&B, or Kilby House. If downtown is full, charming rentals are available in nearby Perry and Lubec.

Extend Your Adventure: From the Coast to the North Woods

After you’ve had your fill of salt spray and pirate gold, head inland to experience the rugged beauty of the Maine Highlands.

Your Luxury Basecamp: Moose River Lookout Located in Rockwood, Maine, Moose River Lookout is the ultimate vacation rental for those who want to transition from “Pirate Life” to “Lake Life.”

• Private Dock: Direct access to Moosehead Lake and the iconic Mt. Kineo.

• Outdoor Paradise: Backyard access to ITS66 for world-class ATVing and hiking.

• Modern Comfort: 3 Bedrooms, 2 Baths, High-Speed WiFi, and a backup generator to ensure your adventure never stops.

Book Your Stay:

• Phone: 800-544-0300

• Email: [email protected]

• Website: MooseRiverLookout.com

Contact the Festival Crew

For volunteer opportunities, vendor applications, or specific event inquiries:

• Director: Melissa Newcomb

• Main Contact: Don — 207-853-0727

• Email: [email protected]

• Official Site: EastportPirateFestival.com

Join the crew this September and create your own legend at the 20th Anniversary Eastport Pirate Festival!