2026 Boothbay Harbor Windjammer Days

Competitors and spectators gathered on the east and west sides of the Footbridge Saturday, June 27 for the annual Server Shuffle, Tug of War Across the Harbor, and the Orne's Candy Store International Rock Skipping Contest. The rock skipping winners have not been announced. The Rock Skipping has been in memory of Arthur Webster since 2019. The competition was established in 2005.

Server Shuffle winners: First Place:  Boothbay Region High School (BRHS) Cheerleaders - 3 minutes, 56…

The U.S. Navy Northeast Band Pops Ensemble concert at the Opera House at Boothbay Harbor drew just shy of a full house Tuesday, June 23. In celebration of the 250th Fourth of July and the region's Windjammer Days, the one-hour show culminated in a standing ovation.

Narration preceded many of the selections that followed the events of the Revolutionary War through the Siege of Yorktown in October 1781. With the aid of France, all active fighting ended and, in Sept.…

The 11th Windjammer Days lobster eating contest June 24 proved the second time can be the charm. Irene Hardesty of South Bristol placed second in the 2025 contest. This year, she won, earning her the $100 prize and bragging rights.

Beginning this year, the contest is being run by the Nelson family: Ted, Cheryl and Ted Jr., who added a few surprises for competitors: an extra knuckle for each person, two of whom would also find their pair of lobsters included a hardshell. Randomly…

What's a festival without fireworks? Following the big events of Parade of Sail and the Street Parade, Wednesday, June 24 concluded with a fireworks show.

The Register once again thanks contributor and professional photographer Mike Leonard for his expertise in shooting the fireworks shows and for sharing with our readers.

The annual Windjammer Days Street Parade takes a lot of work by a lot of people to delight even more people and this year’s edition did not disappoint.

As the…

The bright, blue sky with puffy clouds provided a beautiful backdrop for the 64th annual Windjammer Days Parade of Sail on Wednesday, June 24. 

Boaters and people lining the shore got a wonderful show as the various ships sailed or motored into the harbor.

The 2026 Parade of Sail (or Gathering of the Fleet, as it is sometimes called) was one to remember.

Stinky fish, bulky clothing and a hot afternoon made for a fun Windjammer Days event – the Fish Relay Race – on Commercial Street, Boothbay Harbor on Wednesday, June 24.

Teams of four – adults and kids – dressed in a fisherman's oil skins and carrying two fish and switching off for each leg of the race – ran a short course to win a prize.

Winners were “The Snowmen” from Albuquerque, New Mexico, who won a $100 gift certificate provided by First National Bank. Their time was…

A band of "thieving pirates" landed on our shores as Windjammer Days continued June 24, and they were intent on "pillaging" Boothbay Harbor. If not for a brave band of kids fighting them off in a brief but savage battle, surely all would have been lost.

Pirates, wannabe pirates and curious visitors gathered in Waterfront Park off Commercial Street for a lesson on cannons Wednesday morning, June 24 during the 64th annual Windjammer Days. 

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Eleven contestants stepped up to the plate to see how many hot dogs, buns and all, they could eat in eight minutes during Dunton’s Doghouse’s third annual hot dog eating contest. 

Last year, Matt Stefanilo of Massachusetts set a record by packing away 13 hot dogs in the allotted time, and it remains unbroken.

First place went to Alex…

The Maine Model Yacht Club and Spruce Point Inn hosted the third annual Spruce Point Inn Regatta on June 21 in Boothbay Harbor as part of Boothbay Harbor Windjammer Days.

The event attracted radio-controlled yacht skippers from across Maine and New England, including competitors from Plymouth, Massachusetts, and Mount Desert Island. Sailors competed in three races on a challenging course designed and managed by Race…

The Windjammer Days 2026 Decorated Boat Parade was held Sunday evening, June 21. Here, Register contributor and professional photographer Mike Leonard provided a gallery of the parade.

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Sunny skies before an afternoon thunderstorm blessed the Blessing of the Fleet and Memorial Service on Sunday, June 21.

About 26 boats – lobster, fishing, Coast Guard and harbor master boats – passed by Boothbay Harbor Fish Pier where area clergy, Pastor Glen Carter of Boothbay Baptist Church and  Rev. Patrick Machayi of Our Lady Queen of Peace, blessed the boats with holy water. About 50 people attended the blessing,…

As a lead up to the 250th anniversary of the U.S., and in a spirited celebration to welcoming the Windjammer fleet to town, the Boothbay Harbor Opera House is pleased to announce that three music ensembles representing the United States Navy, will be performing free community concerts June 23 and 24.

On Tuesday, June 23, Navy Band Northeast returns to the historic Opera House with its 30-member wind and percussion Pops Ensemble, performing the show-stopping music of Broadway, as well…

June 21 – 27

*All events subject to change*

Events held in Boothbay Harbor unless otherwise noted.

SUNDAY, JUNE 21

9 a.m. - 4 p.m. - R/C sailing competition at Spruce Point Inn - 88 Grandview Ave. The second annual Windjammer Days SPI Cup! A day of R/C sailboat racing hosted by Maine Model Yacht…

The Boothbay Region's festival founded in 1962 remains the most anticipated event of the year. The 64th annual Windjammer Days week-long festival happens from Sunday, June 21 through Saturday, June 27. 

Windjammers, schooners and yachts confirmed for the 64th festival are: Alert, Applejack, Columbia (new!), Eastwind, Gleam, Harvey Gamage, Heritage, Hesper, Isaac H. Evans, Isabella, Lewis R. French,…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are…

As Boothbay Harbor prepares to celebrate the 64th annual Windjammer Days, this year’s theme proudly honors the past, present, and retired members of the United States Navy who have served our nation with dedication and distinction. Throughout the coming weeks, we will feature a series of profiles highlighting local Navy service members—sharing their stories, experiences, and the lasting impact of their service. These articles are a tribute to the men and…

On June 27, Friends of Windjammers Days hosted a pier party and a display of antique autos and motorcycles. 

One can only imagine the years of work behind keeping these vintage vessels afloat and shining.

The Vintage Boat Parade, led by the Nellie G II in honor of George McEvoy who died recently, led the parade Friday afternoon, June 27 around the inner harbor. The parade is one of the special events of Windjammer Days. 

Unicorns, ducks, giant gummie bears ... and even a couple of people in jail. These were just a few of the scenes from shore as the Decorated Boat Parade passed along the inner harbor on Sunday, June 29. 

Remade from the former Lighted Boat Parade for Windjammers, the parade was postponed from Saturday due to the weather. 

The newspaper would like to thank Mike Leonard for once again coming through for us with his fabulous photos. 

He hammers, forges and pounds metal into shapes of coins similar to those used by pirates and sailors maneuvering ships in the 16th and 17th centuries. Steve Lenhardt owns Black Spot Guild in Coldbrook, New Hampshire, but this week he demonstrated his metal works skills in Whale Park during Windjammer Days.

Lenhardt inquired to the Friends of Windjammer Days' organizing committee last winter about demonstrating his skills at the event. He believed his Spanish-…

The lobster eating contest is one of the most popular events of Windjammer Days, just as it was during the region's former Fishermen's Festival. The contest drew a huge crowd Wednesday, June 25 for the high noon competition. And, for the first time in many years, a woman took the prize.

2025 winner Abby Baker of Brunswick was ecstatic over the win. In a post-contest interview, Baker said what she didn't anticipate was the spray of tomale upon cracking the first lobster body. Other…

A salute to the Coast Guard was the main theme of the annual Windjammer Days Street Parade and several floats sported signs, T-shirts and more to thank the Guard on Wednesday afternoon, June 25.

The parade was filled with three Kora Karts units, the longtime participants The Sailing Masters of 1812 from Essex, Connecticut and the Boothbay Region Community Band, several non-profit groups and lots of kids — many who squirted the onlookers with water, cooling them off in the…

Chaos erupted on the pier June 25 as a band of pirates landed on our shore, intent on taking over the town! Thankfully, they were beaten back after a brief but fierce battle with some newly trained defenders. 

Balloon swords, treasure chest and other tattoos, map making, music and more made for lots of fun for kids and wannabe pirates as the Pirates of the Dark Rose set up a bazaar in Waterfront Park off Commercial Street during the 63rd annual Windjammer Days in Boothbay Harbor.

Also, cannon lessons from one of the pirates drew lots of young students who learned the pieces of equipment to clean, load and fire a cannon.

The pirates were anticipating and gearing up for “The Battle for…

Eleven contestants stepped up to the plate to see how many hot dogs, buns and all, they could eat in eight minutes during Dunton’s Doghouse’s second annual hot dog eating contest. 

Among the competitors was last year’s champ, Dylan Geyer, whose prior record of 10 frankfurters was the one to beat. There were several techniques on display, including the classic water-dip and, in one contestant’s case, eating the dogs…

The Friends of Windjammers Days hosted a dinner and cocktail party June 23 to honor retired and active U.S. Coast Guardsmen at Boothbay Harbor Oceanside Resort. The dinner attracted 16 honorees. According to Friends of Windjammers Days member Laney Hebert, 64 people attended the dinner. 

Among U.S. Coast Guardsmen who attended were Ryan Smith, DJ Holcomb, Doug Snyder, Brian Blethen, Nat Wilson, Rusty Court, Fred Bowers, Bob Cotier, John Foss, Sharon Machon Ames, Bruce MacCormac,…

Boothbay Harbor Memorial Library (BHML) welcomed a shipful of wee mateys June 24 to participate in its annual summer reading challenge, and have fun with its assortment of pirate-themed activities and lawn games. 

The theme this year was "Level Up!" Similar in style to a video game, kids get to choose between four different levels with unique tasks, picking their own adventure path each time there's a fork in the road.

"We're looking at leveling up our reading by doing…

For me, Windjammer Days brings back memories from some 50 odd years of witnessing this special event. There have been lots of changes, but fundamentally, it's a tribute to, by and for a coastal community connected to the seas for centuries and an historic tradition. 

Arrr Mateys! Feast yer eyes on the fine crew of the Spinks and Steffenson families, the first brave souls to set sail on the Boothbay Harbor Treasure Hunt! On Sunday, June 22, they took to the helm like true sea captains, marked their maps with stamps at each destination, and struck a pose behind the Pier 1 photo board, beaming with pride for all to see.

This summer-long quest is sponsored by the nonprofit organization Lighthouse Education & Nautical Studies (LENS) and…

One of the first events of Windjammer Days week was at Boothbay Harbor Inn June 23, the 7th annual Crab Cook-off. The 50-seat event was sold out as local chefs faced off in the kitchen, including last year’s champ Ralph Smith from Mine Oyster, Mike Whitney of Bluebird Ocean Point Inn and Ethan Crosby of Smuggler’s Cove.  

Judges included News Center Maine’s Sharon Rose, Bet Finocchiarro, owner of Bet's Fish Fry, and Kelly Farrin, owner of Carriage House Restaurant.  The…

Boothbay's Got Talent at the Boothbay YMCA kicked off the Windjammer Days Festivities, June 22 at 5 p.m. with six contestants: Oscar Mirabile (age 8, magic act), Lily Billings (age 8, singing and dancing), Agatha Harris (age 9, singing), Violet Baldwin (age 11, singing), Lydia Mitchell (age 11, hula hooping), and Kaylee Wayda (age 12, ventriloquism).

The four judges were Nick Ullo, Mary Ripley, Lisa Walby and Douglas Gimbel.

Oscar Mirabile took first place…

The blue skies with a slight breeze made for great conditions for the 2025 Windjammer Days Blessing of the Fleet and Memorial Service on Sunday afternoon, June 22.

It was the opening event of the week-long festival. About 25 boats participated in the blessing which was conducted by Father Peter Shaba of Our Lady Queen of Peace Catholic Church, Tammy Judkins of United Methodist Church of Boothbay Harbor, Rev. Todd Weir of the Congregational Church of Boothbay Harbor, and Rev. Glen…

Volunteers ... Could as much be accomplished within communities and organizations without them? Case in point: Boothbay Harbor Windjammer Days, a beloved festival that truly takes a village.

As of 2025, the event has been led by Friends of Windjammer Days, an all-volunteer group that has grown the festival to a seven-day, jam-packed happening since 2014. The group formed the previous year following Boothbay Harbor Region Chamber of Commerce's announcement it would be outsourcing the…

The breeze was as strong as the sun during 2024’s Windjammer Days’ Artists Alley down to Whale Park June 27 and 28. Coordinating this event the past two years, is Friends of Windjammer Days member Mary Wawro.

And what a great lineup of artisans she brought to the Park:  Calli B (jewelry), Chris Cambridge (scrimshaw), Stephanie Crossman (handmade fish netting sculpture and paintings), Eric Darling (oil and up-cycled rope paintings), Dianne Horton (watercolors), Laura Kowacki…

Do you believe in ghosts? Or like a side of the metaphysical with your history?

From 1920s booze runners and mysteriously drowned women, to ghosts who love country music and hate it when people change their wallpaper, American Ghost Walks takes visitors on a walking tour of downtown Boothbay Harbor to peer at the spirits hidden within the region’s history. 

Julee…

There was a new event at this year’s Windjammer Days, the server shuffle. Teams of two waitstaff raced down the Footbridge with glasses, champagne flutes and other containers of water on serving trays. Whoever brought back the most liquid in the least time won. With speed and balance, the Thistle Inn team, Amy Stockford and Bianca Bal, took first place beating others from Pier One Pizza, Waves, Carriage House, Whale’s Tale, and Boathouse Bistro. Organizers said they hope to see the…

An antique car show followed the antique boat parade June 28 as part of Day 6 of Winjammer Days at Bristol Marine Shipyard.

A team from Fuller Marine Services won the 2024 Tug Across The Harbor June 29. Fuller Marine Services workers also took the trophy at last year’s tug with help from other crew members working on the newly renovated Footbridge. 

This year, they beat four other teams including Carousel Marina, the Coast Guard, Hell Yeah, from Massachusetts, and the Town Crew, made up of Boothbay Harbor municipal staff. However, the competition was cut short because the Coast Guard team had to…

With a name like Cary Stone, what options do you have but to win a rock skipping contest? Managing 20 skips across the inner harbor, “Mr. Stone” won both the men’s division and most overall skips at the annual Orne's Candy Store International Rock-Skipping Contest June 29. 

In the women’s division, Donna Loonie and Anna Tew both skipped 12 times, leading to a skip-off to determine the winner. Loonie lived up to her skipping name “Rock Launcher” and won the final round with…

The Vintage Boat Parade was held on Day 6 of Windjammer Days in the inner harbor June 28. A large crowd assembled at Whale Park to watch the antique boats.