Alphabetical Quick Links

 

Daily Schedule of Events

SUNDAY, JUNE 21, 2026

9:00 AM- 4:00 PM; Presentation at 5:00 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.

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

6:00 PM
Boothbay’s Got Talent @ Boothbay Region YMCA
Boothbay’s Got Talent is back this year and will be LIVE in 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.

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

7:00 PM
Decorated Boat Parade Starting earlier this year at 7 PM, the new format allows for a stunning display of decorated boats before nightfall, ensuring every colorful detail can be appreciated in full view. Boats circle the harbor twice. Cash prizes and every registered boat receives a $100 fuel card just for participating! Rain date is Saturday, June 27.

Watch Party Decorated Boat Parade Join us at Mine Oyster Restaurant to cheer on the boats as they go by! Drink specials and light appetizers. The party continues with prize announcements and a celebration of the culmination of the 64th Boothbay Harbor Windjammer Days!

MONDAY, JUNE 22, 2026

10:00 AM - 12:00 PM
Mysterious Harbor Tours: Joy Ride E-Bike Tour (Meets at Pedego Electric Bikes)
Immerse yourself in ocean breezes, pine-scented forests, and the world of renowned artists Kim and Philippe Villard whose work resides in MoMA’s permanent collection. Book the Joy Ride Tour

10:00 am - 12:00 PM
Mysterious Harbor Tours: History, Legend & Lore Walking Tour (Meets in Whale Park)
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

1:00 PM - 2:30 PM
Mysterious Harbor Tours: Boos & Brews Walking Ghost Tour (Meets at 1901 Footbridge)
Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to the Footbridge Brewery for craft beer and barbecue. Book the Boos & Brews Tour

1:00 - 3:00 PM
8th 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.

4:00 PM - 5:30 PM
Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour (Meets at 1901 Footbridge)
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

5:00 PM - 6:00 PM
Meet & Greet - Come meet our U.S. Navy honorees at Oceanside. All are welcome.

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

TUESDAY, JUNE 23, 2026

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 at Whale Park
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

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

10:00 AM - 12:00 PM
Mysterious Harbor Tours: Hidden Harbor E-Bike Tour (Meets at Pedego Electric Bikes)
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)
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

10:00 AM - 1:00 PM
Windjammers for Wee Mateys and Summer Reading Kickoff - Tattoo parlor - pirate names, ocean themed books, lawn games, and a craft. Summer Reading Program begins. 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
Hot dog eating contest - Whale Park
for more information contact: duntonsdoghouse@gmail.com

1:30 PM - 3:30 PM
Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour (Meets in Whale Park)
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

3:00 PM
Recruitment of Young Pirates
Whale Park

4:00 PM
Crudbeard’s Cannon Lessons
Whale Park

4:00 PM - 5:30 PM
Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour (Meets at 1901 Footbridge)
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
Free Community Concert: Navy Band Northeast Pops Ensemble; Boothbay Opera House. Doors open at 6:30 PM
One of 11 official Navy bands that tour the U.S. They will be playing pops, Broadway, American, Patriotic music in celebration of Windjammer Days and the 250th birthday of the U.S.A.

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

WEDNESDAY, JUNE 24, 2026

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

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

10:00 AM - 12:00 PM
Mysterious Harbor Tours: Joy Ride E-Bike Tour (Meets at Pedego Electric Bikes)
Immerse yourself in ocean breezes, pine-scented forests, and the world of renowned artists Kim and Philippe Villard whose work resides in MoMA’s permanent collection. Book the Joy Ride Tour

10:00 am - 12:00 PM
Mysterious Harbor Tours: History, Legend & Lore Walking Tour (Meets in Whale Park)
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

10:00 AM - 3:00 PM
Maine State Aquarium - McKown Point Road
Explore how lobsters grow, what they eat, why they are different colors, and who the scientists are that study them. Check out a variety of tanks, hands-on exhibits, and interactive displays. New this year: kelp and scallop aquaculture exhibits! Dive into their fascinating biology, roles in the ecosystem, and Department of Marine Resources’ research. Visit https://shorturl.at/XV2kq for admission fees and other info.

10:30 AM
Crudbeard’s Cannon Lessons
Whale Park

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

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

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

1:30 PM - 3:30 PM
Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour (Meets in Whale Park)
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
Cod Fish Races
Whale Park - Open to all!

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

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

7:00 PM
American Ghost Walks; 22 Granary Way
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 25, 2026

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 - 2:00 PM Boothbay Region Historical Society
U.S. Navy Exhibit

As part of the national celebration honoring the 250th anniversary of America, the Boothbay Region Historical Society is joining with the Windjammers Committee and others to honor the US Navy, created in 1775. This exhibit will highlight the long-standing connection between local shipyards and the Navy. Local BRHS historian Jim Hunt characterized the story as “Iron men in wooden ships.” Click here for more information.

10:00 AM - 3:00 PM
Maine State Aquarium - McKown Point Road
Explore how lobsters grow, what they eat, why they are different colors, and who the scientists are that study them. Check out a variety of tanks, hands-on exhibits, and interactive displays. New this year: kelp and scallop aquaculture exhibits! Dive into their fascinating biology, roles in the ecosystem, and Department of Marine Resources’ research. Visit https://shorturl.at/XV2kq for admission fees and other info.

10:00 AM - 3:00 PM
United States Coast Guard Station - Boothbay Harbor
The Coast Guard will be having an Open house for the general public at the Station: 166 McKown Point Rd, West Boothbay Harbor.

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

FRIDAY, JUNE 26, 2026

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.

10:00 AM - 12:00 PM
Mysterious Harbor Tours: Hidden Harbor E-Bike Tour (Meets at Pedego Electric Bikes)
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 - 2:00 PM Boothbay Region Historical Society
U.S. Navy Exhibit Click here for more information.


10:00 AM - 3:00 PM
Maine State Aquarium - McKown Point Road
Explore how lobsters grow, what they eat, why they are different colors, and who the scientists are that study them. Check out a variety of tanks, hands-on exhibits, and interactive displays. New this year: kelp and scallop aquaculture exhibits! Dive into their fascinating biology, roles in the ecosystem, and Department of Marine Resources’ research. Visit https://shorturl.at/XV2kq for admission fees and other info.

1:00 PM - 2:30 PM
Mysterious Harbor Tours: Boos & Brews Walking Ghost Tour (Meets at 1901 Footbridge)
Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to the Footbridge Brewery for craft beer and barbecue. Book the Boos & Brews Tour

1:30 PM - 3:30 PM
Mysterious Harbor Tours: Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour (Meets in Whale Park)
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

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 - Sample’s 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
American Ghost Walks; 22 Granary Way
Expand your knowledge of the supernatural with local accounts (by reservation only)

SATURDAY, JUNE 27, 2026

10:00 AM - 12:00 PM
Mysterious Harbor Tours: Hidden Harbor E-Bike Tour (Meets at Pedego Electric Bikes)
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)
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

10:00 AM - 2:00 PM Boothbay Region Historical Society
U.S. Navy Exhibit Click here for more information.

10:00 AM - 3:00 PM
Maine State Aquarium - McKown Point Road
Explore how lobsters grow, what they eat, why they are different colors, and who the scientists are that study them. Check out a variety of tanks, hands-on exhibits, and interactive displays. New this year: kelp and scallop aquaculture exhibits! Dive into their fascinating biology, roles in the ecosystem, and Department of Marine Resources’ research. Visit https://shorturl.at/XV2kq for admission fees and other info.

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

11:30 AM -1:00 PM (11:00 AM registration)
21st 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.

1:00 PM Server Shuffle; at Footbridge. The finest local waitresses and waiters compete in a race across the Footbridge.

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.

4:00 PM - 5:30 PM
Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour (Meets at 1901 Footbridge)
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
American Ghost Walks; 22 Granary Way
Expand your knowledge of the supernatural with local accounts (by reservation only)

7:30 PM - Boothbay Opera House
Those familiar with Lucy Wainwright Roche are aware of her bell tone voice, her unshakable melodies, and her knack for wise, wry lyrics that clench the heart. It’s no surprise that as the daughter of Suzzy Roche and Loudon Wainwright III, and half sibling to Rufus and Martha Wainwright, that she grew up on the road, steeped in music. Armed with a guitar, a deadpan sense of humor, killer songs, and a voice that makes tough guys cry, she’s built a solid solo artist following across the US and Europe. Tonight she is joined on the Opera House stage by her mother, Suzzy Roche,founding member of award-winning band, The Roches. Together Lucy and Suzzy have won best singer/songwriter album of the year at the Independent Music Awards. We welcome this talented mother/daughter duo to the stage tonight.

Special advance discounted tickets $25, available from the box office beginning March 18. Regular tickets, $30. Purchase tickets here

““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