Eastport Pirate Festival 2025 | New England’s Biggest Pirate Party on the Maine Coast
- Gerry Caron
- 4 days ago
- 4 min read
Eastport Pirate Festival 2025 | New England’s Boldest Pirate Celebration
Ahoy, adventurers! Get ready to set sail for the 20th Annual Eastport Pirate Festival, the biggest pirate party in New England and the Maritimes, happening September 4–7, 2025. This legendary weekend takes over downtown Eastport, transforming Water Street into a swashbuckling world of pirate knockouts, theatrical flair, and family-friendly escapades—all mostly FREE to attend the Eastport Pirate Festival 2025!
A Weekend Packed with Pirate Punch
Here’s a treasure map of key activities and attractions you won’t want to miss:
Pirate Parade & Float Contest – Build a themed float, don your finest pirate garb, and compete for “loot” prizes (cash awards for best costumes, floats, vehicles, and group entries).
Ravenbane’s Firecraft Show – Prepare to be mesmerized as professional fire performers light up the night with incredible pyro-dramatics
Tortuga Encampment & Pirate Workshops – Learn cutlass fighting, pirate weaponry, and join “Piracy 101” or cannon lessons with seafaring reenactors.
Kids’ Activities Galore – From face painting, water balloon battles, and balloon twisting to youth pirate pageants, scavenger hunts, and photo booths—there’s treasure chest of fun for little buccaneers.
Pop-Up Tavern Games – Test your skills at Horn Run Brewery’s pirate-themed games, and enjoy music and drink specials with a salty twist.
Live Music & Street Performers – Groove to free live music by Rockin’ Ron, local bands, and live performers roaming the streets.
Barrel Races & Costume Contests – Race rum barrels, compete in best pirate costume contests for all ages, from kids to “big kids.
The Black Pearl Ball (Saturday Night) – A formal pirate gala that’s your chance to glitz, glam, and swashbuckle in style—tickets sold via the Eastport Art Center.
Fireworks Finale – Evening fireworks set the sky ablaze in a grand salute to Maine seas, capping off the pirate party with pyrotechnic flair
Festival Schedule at a Glance
Thursday, Sept 4, 2025: Evening festivities kick off (times TBD).
Friday, Sept 5: 10 AM–9 PM — family-friendly activities and vendor markets.
Saturday, Sept 6: 10 AM–11 PM — full pirate immersion, including Black Pearl Ball in the evening.
Sunday, Sept 7: 8 AM–4 PM — wrap-up of games, parade, and one last blast.
Travel Tips & Practical Info
Location: Primarily outdoors along Water Street; some events may shift indoors if weather turns.
Admission & Parking: The festival is FREE, with free parking available (though limited—arrive early or park and walk).
Pro Tips: Bring some cash—many vendors accept cards, but cash is recommended. Costumes encouraged (prop weapons must be safe and sheathed), and yes, you can bring strollers—but pets are discouraged due to crowd energy.
Overnight Accommodations:
Downtown Eastport Options: Motel East, Todd House B&B, Kilby House, Rossport by the Sea, Seaview RV Resort.
Nearby towns offer more stays (Machias River Inn, Perry, Lubec).
A Town Steeped in Pirate & Maritime Charm
Eastport, known as America’s easternmost city, has a storied past rooted in maritime tradition. Since 1772, its harbor has welcomed fishermen, traders, and adventurers, making it the perfect launching point for this legendary pirate festival
Final Parlay
This year’s Eastport Pirate Festival promises to be a bold and jubilant celebration marking 20 legendary years. Join costumed revelers, live performances, cannon lessons, family-friendly games, and a fire-lit finale to create lasting pirate lore of your own. Whether you're swashbuckling in costume or enjoying the seaside spirit, there’s treasure here for every adventurer.
What to Do in the Moosehead Lake Region & Beyond: Your Complete Guide to Outdoor Adventure & Local Attractions
Planning a trip to the Moosehead Lake region in Maine? You're in for an unforgettable experience packed with adventure, breathtaking natural beauty, and cozy lodging options. From high-adrenaline ATV trails to peaceful paddles on glassy waters, the Moosehead Lake area is a four-season playground perfect for outdoor lovers, families, and anyone looking to unplug and explore.
Want more insider tips? Discover top recommendations at Moose River Lookout, your go-to resource for:
🛶 Boating & paddling routes
🎣 Fishing hotspots
🏕️ Wilderness camping sites
🥾 Trail maps for hiking & nature walks
🍽️ Local dining & shopping recommendations
Stay updated with the latest happenings and news in the Moosehead Lake region. Learn more about what to do and where to go in the Moosehead Lake area and beyond.
🏡 Where to Stay: Moose River Lookout – Your Basecamp for Adventure
Located in Rockwood, Maine, Moose River Lookout is the ultimate vacation home rental for adventurers and nature lovers alike. Nestled on the Moose River, this cozy home features:
Private Dock with access to Moosehead Lake
3 Bedrooms | 2 Baths | Sleeps 7
Free WiFi & TV
Backup Generator
Easy driveway access for trailers & ATVs
Direct access to ITS66 Snowmobile Trails
Year-round availability for summer AND winter sports
Whether you're hiking Blue Ridge, casting a line in the river, or hitting the snowmobile trails—Moose River Lookout is where your Maine vacation begins.
Ultimate Outdoor Getaway
With direct backyard access to Maine's Interconnected Trail System (ITS66) and a private dock on the river, adventure awaits right outside your door. Whether you're into hiking, golfing, boating, fishing, hunting, skiing, or snowmobiling, you'll find it all just steps away from our doorstep.
Book Your Stay
Experience the ultimate outdoor getaway in the heart of Maine's natural beauty. For inquiries or to make a reservation, please don't hesitate to contact us. We look forward to welcoming you to Moose River Lookout, lodging Rockwood Maine a Vacation Home Rental, on Moose River with access to Moosehead Lake and Mt. Kineo!
Phone: 800-544-0300
Email: mooseriverlookout@gmail.com
Address: 4054 Rockwood Rd Rockwood, ME 04478
Website: Moose River Lookout
Ahoy, adventurers! Get ready to set sail for the 20th Annual Eastport Pirate Festival, the biggest pirate party in New England and the Maritimes, happening September 4–7, 2025.
