Alphabetical Quick Links

 

Daily Schedule of Events

SUNDAY, JUNE 22, 2025

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 cglnate@comcast.net

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
It is with great disappointment that we must cancel the Lighted Boat Parade for this evening due to the weather. Thank you to all the boat captains and crews who were willing to make the effort. We so appreciate you!!

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!

MONDAY, JUNE 23, 2025

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 24, 2025

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: duntonsdoghouse@gmail.com

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 25, 2025

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 26, 2025

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)

7:30 PM
Tim Sample
Boothbay Opera House

FRIDAY, JUNE 27, 2025

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.

SATURDAY, JUNE 28, 2025

11:00 AM - 4:00 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!
Located in the YMCA Fieldhouse.
Art Opening at the YMCA, featuring local artist Charlie Nowell.  Light refreshments served.

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

7:30 PM
Okan
Boothbay Opera House

““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

Contact us at windjammerdays@gmail.com or P.O. Box 101, Boothbay Harbor, ME 04538