Daily Schedule of Events

SUNDAY, JUNE 23, 2024

8:00 AM- 4:30 PM
R/C sailing competition at Spruce Point Inn
Spruce Point Inn and the Maine Model Yacht Club (MMYC) to host a day of R/C sailing competition and spectating at the Spruce Point Inn dock and oceanside pool. Click on link for more information.

1:00 PM
Boothbay Harbor One Design Association Fun Sail
For more information contact Nate Cagle at cglnate@comcast.net

6:00 PM
Boothbay’s Got Talent
Boothbay’s Got Talent is back this year and will be LIVE at the YMCA! This year’s competition includes two categories: The Royal Windjammer (Ages 7-12) and Top Royal (ages 13-18). There is not a gender assigned to either title. 


MONDAY, JUNE 24, 2024

1:00 - 3:00 PM
6th Annual Windjammer Days Crab Cake Cook Off
Boothbay Harbor Inn

3:30-5:00 PM
Meet & Greet - Boothbay Region Boat Builders
Boothbay Harbor Oceanside Golf Resort
Just like every boat has a story to tell, so does every boatbuilder. This year each of our schooner sponsors have chosen a local shipwright to honor during Windjammer Days.


TUESDAY, JUNE 25, 2024

7:00 AM - 9:00 AM
Pancake Breakfast
Whale Park

9:00 AM - 5:00 PM
Friends of Windjammer Days Tent Open Information available. Raffle tickets with prizes every hour!

10:00 AM - 1:00 PM
Kids Alley
Whale Park

10:00 AM – 10:30 AM
Pirates of the Dark Rose Puppet Show
Whale Park

10:00 AM - 1:00 PM
Windjammers for Wee Mateys and Summer Reading Kickoff
Boothbay Harbor Memorial Library Lawn

11:00 AM - 1:00 PM
Pirates Tortuga Open
Pirate bazaar with games and activities in Whale Park

11:30 AM
Crudbeard’s Cannon Lessons
Whale Park

2:00 PM
Pirates of the Dark Rose Weapon Show
Whale Park

3:00 PM
Recruitment of Young Pirates
Whale Park

4:00 PM
Crudbeard’s Cannon Lessons
Whale Park


WEDNESDAY, JUNE 26, 2024

7:00 AM - 9:00 AM
Pancake Breakfast
Whale Park

9:00 AM - 9:00 PM
Friends of Windjammer Days Tent Open in Whale Park Raffle tickets with prizes every hour with grand prize drawing at 8 pm

10:00 AM - 4:00 PM
Maine State Aquarium - McKown Point Road
It’s the 2024 preview opening! New tanks, interactive exhibits and hands-on activities. The popular touch tank and a preview of what the final redesigned aquarium will be. Also a great place to watch the Windjammer fleet sailing outside the harbor before the Gathering of the Fleet!

10:00 AM - 11:00 AM
Pirates of the Dark Rose Tortuga Open
Pirate bazaar with games and activities in Whale Park

10:30 AM
Crudbeard’s Cannon Lessons
Whale Park

12:00 PM
The Battle for Boothbay Harbor
Live cannon fire and the clash of swords
High Noon Whale Park

12:30 PM
Lobster Eating Contest
Whale Park - Open to all!

1:00 PM - 3:00 PM
Gathering of the Fleet

2:00 PM - 3:00 PM
Pirates of the Dark Rose Tortuga Open
Pirate bazaar with games and activities in Whale Park

2:00 PM
Cod Fish Races
Whale Park - Open to all!

2:00 PM - 3:00 PM
Pirates of the Dark Rose Ship’s Rail Open
Whale Park Public Landing

4:00 PM
Street Parade
Begins at the high school and proceeds downtown

7:00 PM - 8:30 PM
American Ghost Walks
Expand your knowledge of the supernatural with local accounts (by reservation only)

9:00 PM
Fireworks Spectacular over the Harbor 


THURSDAY, JUNE 27, 2024

7:00 AM- 11:00 AM
Windjammer Fleet Leaves the Harbor
Bid the schooners farewell as they depart Boothbay Harbor

9:00 AM - 5:00 PM
Artist’s Alley
Whale Park

9:00 AM - 12:00 Noon
Boothbay Farmer’s Market
Boothbay Common

7:00 PM
Boothbay Summer Theater
Carousel Music Theater, 196 Townsend Avenue

MY WITCH: The Margaret Hamilton Stories is a one-woman tour-de-force starring New York’s Jean Tafler.

7:00 PM - 8:30 PM
American Ghost Walks
22 Granary Way

Expand your knowledge of the supernatural with local accounts (by reservation only)


FRIDAY, JUNE 28, 2024

9:00 AM - 5:00 PM
Artists Alley
Whale Park

4:00 PM
Annual Vintage Boat Parade & Pier Party
Watch the parade circle the harbor then view them up close at The Shipyard for the after party (tickets required)

4:30 PM - 7:00 PM
Vintage Boat Parade & Pier Party
The Shipyard in Boothbay Harbor (tickets required)

7:00 PM
Boothbay Summer Theater
Carousel Music Theater, 196 Townsend Avenue

MY WITCH: The Margaret Hamilton Stories is a one-woman tour-de-force starring New York’s Jean Tafler.

7:30 PM
Tim Sample
Boothbay Opera House


SATURDAY, JUNE 29, 2024

11:00 AM - 2:00 PM
Boat Bar Party…come Skip, Tug & Be Merry
22 Granary Way

11:00 AM registration; 11:30 AM -1:00 PM
18th Annual Orne's Candy Store International Rock-Skipping Contest (in memory of Arthur Webster)
Benefit of the
Boothbay Region Health Center and the Maine Lobstermen's Association.

11:00 AM - 2:00 PM
Boothbay Harbor Memorial Library Fundraiser
Fundraiser will be on the library lawn.
The Boothbay Harbor Memorial Library Trustees will host a Carnival Fundraiser to promote and raise funds for Children's programming. There will be a bounce house, lawn games, face painting, and more.

1:00 PM - 2:00 PM
Tug Across The Harbor
Best viewing is from the footbridge in the center of town

2:00 PM - 3:00 PM
Server Shuffle -
The finest local waiters and waitresses compete in a race across the Footbridge to determine who has the steadiest hand while carrying a tray of drinks.

5:00 PM - 7:00 PM
Art Opening at the Boothbay Region Y!
Fundraiser will be on the library lawn.
Featuring local artist Charlie Nowell. Includes Tours of the Art around the Y

7:00 PM
Boothbay Summer Theater
Carousel Music Theater, 196 Townsend Avenue

MY WITCH: The Margaret Hamilton Stories is a one-woman tour-de-force starring New York’s Jean Tafler.

Also: June 30 at 3:00 PM

“The rocky coastline and rippled blue waters are just a slice of what makes Boothbay Harbor so easy on the eyes. Accented by sailboats off the coast and antique lighthouses, the seaside town is a nautical delight.”
— Expedia Viewfinder Names Boothbay Harbor the Most Beautiful Town in the State of Maine