Windjammer Days marks the kick off to summer in the Boothbay region and is a time to reconnect with family, friends and neighbors after the long winter, an opportunity to support local businesses and welcome visitors. It is a time to honor our maritime history and celebrate the vital role it plays in the lives of all who live here.

Schedule of Evnets

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.

12:30 PM
Boothbay Harbor One Design Association Fun Sail
For more information contact Nate Cagle at [email protected]

1:30 PM
Blessing of the fleet (open to all commercial fishing vessels)
Viewing can take place at the Fisherman's Memorial or any place in the harbor.

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.

9:00 PM
Harbor Aglow
Help us make the harbor glow! Join in on the parade circling the harbor or light up at your slip or mooring in the harbor. Win prizes and bring joy to the harbor!

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.

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

1:30 PM - NEW EVENT!
Hot dog eating contest - Whale Park
for more information contact: [email protected]

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

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

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

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

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

Date: June 23-29, 2024

Location: Various Venues in Boothbay Harbor, ME

Click here for more information