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
Come watch the races at the 2nd annual Windjammer Days SPI Cup! This day of R/C sailboat racing hosted by the Maine Model Yacht Club will feature some of the best competitors in New England’s R/C sailing community. Click on link for more information.

10:00 AM - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

12:30 PM
Boothbay Harbor One Design Association Fun Sail
For more information contact Nate Cagle at cglnate@comcast.net

1:00 PM - 3:00 PM
Joy Ride E-Bike Tour
Experience the breath-taking beauty of the Boothbay peninsula with all five senses with a visit to Villard Studios. At Pedego Electric Bikes

1:30 PM
Blessing of the fleet (open to all commercial fishing vessels)
The blessing is performed at the Atlantic Edge dock followed by the outside memorial service at the adjacent Fisherman's Memorial Park on Atlantic Avenue. Viewing of the boats and blessing can take place at the Fisherman’s Memorial or any place in the harbor. Click here for more details

4:00 PM - 5:30 PM
Mysterious Lore & More Walking Tour - At Whale Park
Travel deep into the heart of Boothbay Harbor’s long and mysterious history.

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 23, 2025
9:00 AM; 1:00 PM and 4:00 PM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

10:00 AM - 11:30 AM
Mysterious Lore & More Walking Tour - At Whale Park
Travel deep into the heart of Boothbay Harbor’s long and mysterious history.

1:00 PM - 2:30 PM
Boos & Brews Walking Ghost Tour - At Footbridge
Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to the Footbridge Brewery for craft beer and barbecue.

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

Come witness local chefs competing for the most mouthwatering crab cake in Boothbay Harbor judged by a celebrity panel. Sure to attract a crowd of foodies and spectators alike, this event will help support Windjammer Days. Advance tickets required.

3:30-5:00 PM
Meet & Greet - United States Coast Guard
At Oceanside This year each of our schooner sponsors have chosen a Coast Guardsman or Coast Guardswoman to honor during Windjammer Days. Open to the public

4:00 PM - 5:30 PM
Spooks & Spirits Walking Ghost Tour - At Footbridge
Unveil Boothbay Harbor’s eerie side with goosebump-inducing stories and a visit to Neat Whiskey Bar.

6:00 PM
How I Became a Pirate! The Musical! - Opera House
Sail off on a fantastic musical excursion when a band of comical pirates lands in Boothbay Harbor looking for an expert digger to join their crew. Braid Beard and his mates enlist young Jeremy Jacob as they look for the perfect spot to bury their treasure. Jeremy finds that adventuring can be lots of fun, but also learns that love and home are treasures you can’t find on any map! The whole family will love this delightful and swashbuckling musical adventure.

This production is performed by members of the Y Arts program. General Admission $10.

TUESDAY, JUNE 24, 2025

7:00 AM - 9:00 AM
Pancake Breakfast - Whale Park
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 Information available. Raffle tickets with prizes every hour!

9:00 AM - 5:00 PM
Pirate Coin forging
Whale Park

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 - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

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

1:00 PM and 4:00 PM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

1:00 PM - 2:30 PM
Paranormal Pedal E-Bike Tour - At Pedego Electric Bikes
Get up close and personal with Boothbay Harbor’s mysterious side and discover why it’s chock full of ghosts, mysterious creatures, and UFO’s!

1:30 PM
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

4:00 PM - 5:30 PM
Boos & Brews Walking Ghost Tour - At Footbridge
Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to the Footbridge Brewery for craft beer and barbecue.

5:00 PM
How I Became a Pirate! The Musical! - Whale Park
Sail off on a fantastic musical excursion when a band of comical pirates lands in Boothbay Harbor looking for an expert digger to join their crew. Braid Beard and his mates enlist young Jeremy Jacob as they look for the perfect spot to bury their treasure. Jeremy finds that adventuring can be lots of fun, but also learns that love and home are treasures you can’t find on any map! The whole family will love this delightful and swashbuckling musical adventure.

This production is performed by members of the Y Arts program. Suggested donation: $10.

WEDNESDAY, JUNE 25, 2025

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

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 - 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

9:00 AM - 5:00 PM
Pirate Coin forging
Whale Park

9:00 AM; 1:00 PM and 4:00 PM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

10:00 AM - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

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

1:00 PM - 3:00 PM
Joy Ride E-Bike Tour - At Pedego Electric Bikes
Experience the breath-taking beauty of the Boothbay peninsula with all five senses with a visit to Villard Studios.

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 Find a cozy establishment in the harbor, or stake your spot along the shore and watch the fireworks light the sky over the majestic masts of the windjammers!

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
Artists Alley - Whale Park
Enjoy the talents of brilliant artists and craftsmen, and delight in some creative demonstrations taking place on Thursday and Friday.

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

10:00 AM - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

10:30 AM - 1:30 PM
Foodie Tour - Advance reservations required
This walking tour introduces a mix of some of the area’s oldest and newest establishments while showcasing the culinary creativity that is alive and well in Boothbay Harbor!  Approximately 1.5 miles mainedayventures.com

1:00 PM and 4:00 PM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

1:00 PM - 3:00 PM
Paranormal Pedal E-Bike Tour - At Pedego Electric Bikes
Get up close and personal with Boothbay Harbor's mysterious side and discover why it's chock full of ghosts, mysterious creatures, and UFOs!

4:00 PM - 5:30 PM
Spooks & Spirits Walking Ghost Tour - At Footbridge
Unveil Boothbay Harbor's eerie side with goosebump-inducing stories and a visit to Neat Whiskey Bar.

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 Boothbay Opera House
Tim Sample After 50 years of touring and telling the best of Maine stories, Tim has announced his “farewell tour” for 2025, and his final performance will be where it all began, in Boothbay Harbor. The box office is open Wednesday-Friday from 10-2. 

FRIDAY, JUNE 27, 2025

9:00 AM - 5:00 PM
Artists Alley - Whale Park
Enjoy the talents of brilliant artists and craftsmen, and delight in some creative demonstrations taking place on Thursday and Friday.

9:00 AM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

10:00 AM - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

10:30 AM - 1:30 PM
Foodie Tour - Advance reservations required
This walking tour introduces a mix of some of the area’s oldest and newest establishments while showcasing the culinary creativity that is alive and well in Boothbay Harbor!  Approximately 1.5 miles mainedayventures.com

1:00 PM - 3:00 PM
Joy Ride E-Bike Tour - At Pedego Electric Bikes
Experience the breath-taking beauty of the Boothbay peninsula with all five senses with a visit to Villard Studios.

4:00 PM - 5:30 PM
Mysterious Lore & More Walking Tour - At Whale Park
Travel deep into the heart of Boothbay Harbor’s long and mysterious history.

4:00 PM
Annual Vintage Boat Parade
A fleet of vintage boats (25+ years old) will grace our harbor in a regal parade of vessels. Join us after the parade at the Pier Party. Advance tickets required.

4:30 PM - 7:00 PM
Pier Party - The Shipyard in Boothbay Harbor
Enjoy appetizers, drinks (full bar), view the vintage boats tied up at the docks, groove to some great live music, and new this year - enjoy a gathering of a vintage motorcycles along with vintage cars at the shipyard! Advanced tickets required.

7:00 PM
Boothbay Summer Theater - Carousel Music Theater, 196 Townsend Avenue
RED, the Tony award-winning play by John Logan. RED is the compelling account of a giant of the art world, abstract expressionist Mark Rothko, as he struggles to synthesize his growing fame with his artistic purity in this Tony Award-winning play. While matching wits with his ‘modern’ apprentice, Rothko embarks on a startling and explosive exploration of the meaning of art, emotion, and authenticity in a commercialized world, all while the fate of his most celebrated group of paintings hangs in the balance.

7:30 PM
I Draw Slow - Final Show. Get your tickets early!
Boothbay Opera House

This critically acclaimed roots five piece Irish band  is currently touring their fifth and most exciting album to date. The band has consistently redefined roots music over four celebrated albums. Their last reached #1 in the Irish Independent Chart. Their songs are streamed in the millions worldwide and the band is in tour-demand in the US, UK, and across Europe. Their distinctive blend of Irish and Appalachian roots composition has been licensed for film, TV, and advertising and is widely covered and recorded by other artists. The band recently appeared in a major Kerrygold butter commercial which featured one of their songs, Swans. Their first Opera House appearance! Advance tickets $25, regular tickets $30 – available beginning March 21.

SATURDAY, JUNE 28, 2025

9:00 AM; 1:00 PM and 4:00 PM
History Tour - Advance reservations required
Travel back in time with us on this scenic two hour stroll as your tour guide regales you with stories and facts dating back centuries in this quaint fishing village.  Suitable for all ages.  Approximately 2 miles. mainedayventures.com

10:00 AM - 12:00 PM
Hidden Harbor E-Bike Tour - At Pedego Electric Bikes
Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history.

10:30 AM - 1:30 PM
Foodie Tour - Advance reservations required
This walking tour introduces a mix of some of the area’s oldest and newest establishments while showcasing the culinary creativity that is alive and well in Boothbay Harbor!  Approximately 1.5 miles mainedayventures.com

11:00 AM - 4:00 PM
Boat Bar Party…come Skip, Tug & Be Merry
The events held throughout the day include a Rock Skipping Contest, Tug Across the Harbor and the Server Shuffle!  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
Join us for a day of fun, excitement, and friendly rivalry as we pit teams against each other in a test of strength and teamwork across the breathtaking Boothbay Harbor in Maine! Best viewing is from the footbridge in the center of town.

1:00 PM - 3:00 PM
Paranormal Pedal E-Bike Tour - At Pedego Electric Bikes
Get up close and personal with Boothbay Harbor's mysterious side and discover why it's chock full of ghosts, mysterious creatures, and UFOs!

4:00 PM - 5:30 PM
Boos & Brews Walking Ghost Tour - At Footbridge
Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to the Footbridge Brewery for craft beer and barbecue.

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

RED, the Tony award-winning play by John Logan. RED is the compelling account of a giant of the art world, abstract expressionist Mark Rothko, as he struggles to synthesize his growing fame with his artistic purity in this Tony Award-winning play. While matching wits with his ‘modern’ apprentice, Rothko embarks on a startling and explosive exploration of the meaning of art, emotion, and authenticity in a commercialized world, all while the fate of his most celebrated group of paintings hangs in the balance.

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!

““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