When & Where to Find Windjammer Days Events!

7:00 AM – 9:00 AM
Pancake Breakfast – Whale Park, 30 Commercial St, Boothbay Harbor.  Come enjoy a delicious breakfast in downtown Boothbay Harbor at Whale Park cooked up for you by some local Fire Fighters!  All proceeds from this event will benefit our local fire department to help them keep us safe.

9:00 AM – 5:00 PM
Friends of Windjammer Days Tent Open at Whale Park, 30 Commercial St, Boothbay Harbor. Information available. Raffle tickets with prizes every hour!

9:00 AM – 5:00 PM
Pirate Coin forging at Whale Park  30 Commercial St, Boothbay Harbor.  Watch “Silverstrike” Steve of the Black Spot Guild as he forges solid silver pirate coins using the same method they used in the 1600s.

10:00 AM – 1:00 PM
Kids Alley – crafts and activities for the kids
Whale Park, 30 Commercial St, Boothbay Harbor.

10:00 AM – 10:30 AM
Pirates of the Dark Rose Puppet Show
Whale Park, 30 Commercial St, Boothbay Harbor.

10:00 AM – 12:00 PM
Windjammers for Wee Mateys,– Boothbay Harbor Memorial Library, 4 Oak St, Boothbay Harbor.  Drop yer anchor on the library lawn for an afternoon of pirate stories and mermaid tales. Get yer arm inked in our (temporary) tattoo parlor, get seaworthy with some face painting, and grab some pirate-y accessories to wear for our pirate-themed story time.

10:00 AM – 12:00 PM
Mysterious Harbor Tours: Hidden Harbor E-Bike Tour (Meets at Pedego Electric Bikes, 185 Townsend Ave, Boothbay Harbor)
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history. Book the Hidden Harbor E-Bike Tour

10:00 am – 12:00 PM
Mysterious Harbor Tours: History, Legend & Lore Walking Tour (Meets in Whale Park, 30 Commercial St, Boothbay Harbor)
Experience stories about Boothbay Harbor’s colonial history and unsolved mysteries. We’ll discuss our smuggling era, island legends, and the Red Paint People. Book the History, Legend & Lore Tour

11:00 AM – 1:00 PM
Pirates Tortuga Open
Pirate bazaar with games and activities in Whale Park, 30 Commercial St, Boothbay Harbor

11:30 AM
Crudbeard’s Cannon Lessons
Whale Park, 30 Commercial St, Boothbay Harbor

12:00-1:00 PM
Navy Band Northeast’s Jack Tar Brass Ensemble, Eastside Waterfront Park, 68 Atlantic Ave, Boothbay Harbor
New Orleans/Dixieland/Pop. Grab a bite in town or bring a picnic lunch and also enjoy the Windjammers from this vantage point.

1:30 PM
Hot dog eating contest – Whale Park
30 Commercial St, Boothbay Harbor.  For more information contact: [email protected]

1:30 PM – 3:30 PM
Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour (Meets in Whale Park, 30 Commercial St, Boothbay Harbor)
Enjoy a movable feast featuring tasting stops at locally owned restaurants and specialty shops where you’ll eat like a local and enjoy shopping options. Book the Boothbay Bites Tour

2:00 PM
Pirates of the Dark Rose Weapon Show
Whale Park, 30 Commercial St, Boothbay Harbor

3:00 PM
Recruitment of Young Pirates
Whale Park, 30 Commercial St, Boothbay Harbor

4:00 PM
Crudbeard’s Cannon Lessons
Whale Park, 30 Commercial St, Boothbay Harbor

4:00 PM – 5:30 PM
Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour (Meets at 1901 Footbridge, meet in the middle at the benches)  With stories of UFOs over Boothbay Harbor to a phantom-filled Opera House, our ghost tour ends on a spirited note with Neat Whiskey Bar’s experiential cocktails. Book the Spooks & Spirits Tour

7:00 PM; Doors open at 6:30 PM
Navy Band Northeast Pops Ensemble; Boothbay Opera House.
Free Community Performance celebrating Windjammers and 250 years of the USA.  Navy Band Northeast hails from Newport, RI and is one of 11 nationally touring bands of the US Navy. Join the gathering tonight for a big band sound bringing the music of Broadway, Americana and patriotic songs to the stage. All ages. No tickets required.

7:00 PM
American Ghost Walks; 22 Granary Way
Expand your knowledge of the supernatural with local accounts (by reservation only)