2026 Windjammer Days Events Schedule
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 Club. Awards at 5 p.m.
1:30 p.m. - Blessing of the Fleet – Captains line up to pass by dock at Atlantic Edge on Atlantic Avenue to be blessed by local clergy for a safe new fishing season. Popular viewing spots: Fishermen’s Memorial Park (across from the Catholic Church), Whale Park on Commercial Street, footbridge.
6 p.m. – Boothbay’s Got Talent - Youth compete for one of two titles: The Royal Windjammer (7-12) and Top Royal (13-18) — neither title is gender assigned — through performance, singing, acting, etc. Winners crowned. Boothbay Region YMCA gym, 261 Townsend Ave.
7 p.m. - American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
7 p.m. – Decorated Boat Parade – New format: Check out the display of boats decorated at the docks; then will parade twice around the harbor.
7 p.m. - Boat Parade Watch Party - Join the Friends of WJD at Mine Oyster to cheer, oooh and ahhh on Pier 1. Drink specials and light appetizers. Prize announcements!
MONDAY, JUNE 22
10 a.m. – Noon - Mysterious Harbor Tours: Joy Ride E-Bike Tour - Immerse yourself in ocean breezes, pine-scented forests, and a visit to the studios of artists Kim and Philippe Villard. FMI/Tickets: https://mysteriousharbortours.com/
10 a.m. – Noon: Mysterious Harbor Tours: History, Legend & Lore Walking Tour - Experience stories about Boothbay Harbor’s colonial history and unsolved mysteries. We’ll discuss our smuggling era, island legends, and the Red Paint People. FMI/Tickets: https://mysteriousharbortours.com/
1 - 2:30 p.m. - Mysterious Harbor Tours: Boos & Brews Walking Ghost Tour - Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to Footbridge Brewery for craft beer and barbecue. FMI/Tickets: https://mysteriousharbortours.com/
1-3 p.m. - Crab Cake Cook Off - Local chefs compete to create the tastiest, original crab cake in Boothbay Harbor. Celebrity judges. Event is a fundraiser in support of Windjammer Days. Advance tickets required. FMI/Tickets: https://shorturl.at/UCgdJ
4 – 5:30 p.m. - Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour - Stories of UFOs over Boothbay Harbor to a phantom-filled Opera House, our ghost tour ends on a spirited note at the Neat Whiskey Bar. FMI/Tickets: https://mysteriousharbortours.com/
5-6 p.m. - Meet & Greet – Stop by Boothbay Harbor Oceanside Inn at 35 Atlantic Ave. and meet many of the U.S. Navy honorees. All are welcome.
7 p.m. - American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
TUESDAY, JUNE 23
7-9 a.m. – Pancake Breakfast – Cooked and served by local firefighters. Whale Park
9 a.m. – 5 p.m. - Friends of Windjammer Days Info Tent – At Whale Park. Boothbay Register Windjammer Days guides, commemorative T-shirts and other items; water and beverages. Raffle tickets sold here for prizes awarded hourly! Grand prize awarded on Wednesday at 8 p.m.!
9 a.m. – 5 p.m. – Pirate Coin Forging – Whale Park. Old Silverstrike Steve forges solid silver pirate coins just as his ancestors did in the 1600s ... when you’ve got nothin' but time ...
10 – 10:30 a.m. – Pirate Puppet Show – Using various toys (think Mr. Potato Head), props and who-knows what, pirates tell a tale of buried treasure. Whale Park.
10 a.m. – Noon - Mysterious Harbor Tours: Hidden Harbor E-Bike Tour - Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history. FMI/Booking: https://mysteriousharbortours.com/
10 a.m. – Noon - Mysterious Harbor Tours: History, Legend & Lore Walking Tour - Experience stories about Boothbay Harbor’s colonial history and unsolved mysteries. Includes the region’s smuggling era, island legends and the Red Paint People. FMI/Booking: https://mysteriousharbortours.com/
10 a.m. - 1 p.m. - Kids Alley - Whale Park. Lots ofcrafts and activities for the kids.
10 a.m. - 1 p.m. – Windjammers for Wee Mateys – Boothbay Harbor Memorial Library lawn. Ocean-themed books, temporary pirate tattoos, lawn games, crafts.
11 a.m. – 1 p.m. – Pirate Tortuga – Pirate bazaar with games and activities. Whale Park.
11:30 p.m. – Cannon Lessons – With pirate Capt. Crudbeard in Whale Park.
1:30 – 3:30 p.m. - Mysterious Harbor Tours: Boothbay Bites Walking Foodie Tour - 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. FMI/Booking: https://shorturl.at/B1jEX
1:30 p.m. – Hot Dog Eating Contest – Whale Park. FMI: duntonsdoghouse@gmail.com
2 p.m. – Pirates Weapon Show – Whale Park. Learn about handling a cutlass, axe and more.
3 p.m. – Recruitment of Young Pirates – Whale Park. Learn the ways of the pirate and his/her weapons.
7 p.m. - U.S. Navy Band Pops Ensemble - Opera House at Boothbay Harbor. Free community performance celebrating Windjammer Days and 250 years of the USA. Music of Broadway, Americana and patriotic songs. All ages. No tickets required. Doors open at 6:30 p.m.
4 p.m. – Cannon Lessons – Led by Pirate Captain Crudbeard
4-5:30 p.m. – Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour - Stories of UFOs over Boothbay Harbor to a phantom-filled Opera House, our ghost tour ends on a spirited note at the Neat Whiskey Bar. FMI/Tickets: https://mysteriousharbortours.com/
7 p.m. - American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
WEDNESDAY, JUNE 24
7 – 9 a.m. Pancake Breakfast - Whale Park. Served up by local firefighters. All proceeds from this event benefit our local fire departments.
9 a.m. – 5 p.m. – Pirate Coin Forging - Back by popular demand! Whale Park. See Tuesday listing for details.
9 a.m. – 9 p.m. - Friends of Windjammer Days Tent - Open in Whale Park. Information, commemorative soft goods, raffle tickets sold for prizes awarded hourly. Grand prize drawing at 8.
10 a.m. – Noon - Mysterious Harbor Tours: Joy Ride E-Bike Tour - Meet at Pedego Electric Bikes in the Meadow Mall. Immerse yourself in ocean breezes, pine-scented forests, and a vistit to the studios of artists Kim and Philippe Villard. FMI/tickets: https://mysteriousharbortours.com/
10 a.m. – Noon - Mysterious Harbor Tours: History, Legend & Lore Walking Tour - Experience stories about Boothbay Harbor’s colonial history and unsolved mysteries. We’ll discuss our smuggling era, island legends and the Red Paint People. FMI/tickets: https://mysteriousharbortours.com/
10 a.m. – 3 p.m. - Maine State Aquarium Activities – McKown Point Road, West Boothbay Harbor. Learn about lobsters and the scientists who study them. See the variety of tanks, hands-on exhibits, and interactive displays. New this year: kelp and scallop aquaculture exhibits. 10 a.m. to 3 p.m. Visit https://shorturl.at/XV2kq for admission fees and other info.
10 – 11 a.m. – Pirate Tortuga Open - A bazaar with games and activities in Whale Park.
10:30 a.m. – Cannon Lessons – Instruction with Pirate Crudbeard in Whale Park.
High Noon – The Battle for Boothbay Harbor – At Whale Park with live cannon fire and the clashing of swords. Youth recruits get to show off their newfound skill and intel.
Noon – 12:30 p.m. – Lobster Eating Contest! – Another favorite for competitors and spectators. Sign up at the Friends of WJD tent on the waterfront.
Noon - Navy's Jack Tar Brass Band - At Eastside Waterfront Park, Atlantic Avenue - free! - Bring your own lawn chair.
1-3 p.m. – The Gathering of the Fleet! – Visiting and local schooners begin entering the harbor, often with cannon fire announcing each historic vessel’s arrival.
2 p.m. - Navy's Crosswinds Woodwind Ensemble - Free concert on the steps of Boothbay Harbor Memorial Library, 4 Oak St.
2 p.m. - Fish Relay Races – Teams race wearing fishermen’s rain gear and carrying two large fish. Commercial Street. A spectator favorite!
2 – 3 p.m. – Pirate Tortuga – A bazaar with pirate games and activities. Whale Park.
4 p.m. - Street Parade - Begins at Boothbay Region High School, up Townsend Avenue toward downtown on Commercial Street.
7 p.m. - American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
9 p.m. Fireworks! – Best viewing by land: Fishermen’s Memorial Park, Atlantic Avenue; Whale Park, footbridge, and lodging around the inner harbor.
THURSDAY, JUNE 25
10 a.m. – 2 p.m. - U.S. Navy Exhibit – Running through Saturday, June 27 - At Boothbay Region Historical Society, 72 Oak St. Honoring the 250th anniversary of America and the U.S. Navy, created in 1775. This exhibit will highlight the long-standing connection between local shipyards and the Navy. BRHS historian Jim Hunt characterized the story as “Iron men in wooden ships.” FMI: https://shorturl.at/Adilm
9 a.m. – 5 p.m. – Artists Alley – Artists and artisans gather in Whale Park. Artist demos; paintings, prints, jewelry, pottery, stained glass, baskets, home and holiday décor, and so much more. Don’t forget your cash!
7 p.m. – American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
FRIDAY, JUNE 26
9 a.m. – 5 p.m. – Artists Alley – Artists and artisans gather in Whale Park. Artist demos; paintings, prints, jewelry, pottery, stained glass, baskets, home and holiday décor, and so much more. Don’t forget your cash!
10 a.m. – Noon - Mysterious Harbor Tours: Hidden Harbor E-Bike Tour - Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history. FMI/Booking: https://mysteriousharbortours.com/
10 a.m. – 2 p.m. - U.S. Navy Exhibit – Running through Saturday, June 27 - At Boothbay Region Historical Society, 72 Oak St. Honoring the 250th anniversary of America and the U.S. Navy, created in 1775. This exhibit will highlight the long-standing connection between local shipyards and the Navy. BRHS historian Jim Hunt characterized the story as “Iron men in wooden ships.” FMI: https://shorturl.at/Adilm
1 – 2:30 p.m. - Mysterious Harbor Tours: Boos & Brews Walking Ghost Tour - Uncover Boothbay Harbor’s unexplained past with spine-tingling tales and a visit to Footbridge Brewery for craft beer and barbecue. FMI/Booking: https://shorturl.at/UaG3E
1:30 - 3:30 p.m. - 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. FMI/Tickets: https://shorturl.at/1fmFX
4 p.m. - Annual Vintage Boat Parade – Vessels 25-plus years old gather in a parade, with announcer, around the inner and outer harbor.
4:30 – 7 p.m. – Pier Party at Sample’s Shipyard - Advance tickets required. 120 Commercial St. FMI/tickets, visit https://www.boothbayharborwindjammerdays.org/. Music, appetizers, drinks (full bar); check out the antique motorcycles and cars.
7 p.m. – American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
SATURDAY, JUNE 27
10 a.m. – 2 p.m. - U.S. Navy Exhibit – Running through Saturday, June 27 - At Boothbay Region Historical Society, 72 Oak St. Honoring the 250th anniversary of America and the U.S. Navy, created in 1775. This exhibit will highlight the long-standing connection between local shipyards and the Navy. BRHS historian Jim Hunt characterized the story as “Iron men in wooden ships.” FMI: https://shorturl.at/Adilm
10 a.m. – Noon - Mysterious Harbor Tours: Hidden Harbor E-Bike Tour - Take the road less traveled, leading to some truly mysterious locations to explore Boothbay Harbor’s hidden history. FMI/Booking: https://mysteriousharbortours.com/
10 a.m. – Noon - Mysterious Harbor Tours: History, Legend & Lore Walking Tour - Experience stories about Boothbay Harbor’s colonial history and unsolved mysteries. We’ll discuss our smuggling era, island legends, and the Red Paint People.
11 a.m. – 4 p.m. - Boat Bar Party - Chowder House, 22 Granary Way. Entry tickets include lobster rolls and fish fry. Cash bar serving beer, wine and specialty mixed beverages. Great viewing spot for the day’s competitions.
11 a.m – 1 p.m. - 20th annual Orne's Candy Store International Rock-Skipping Contest - Registration at 11 in the footbridge parking lot. Skipping begins at 11:30. Categories: Kids (to age 12), men’s, women’s divisions. Prizes! Held in remembrance of Arthur Webster.
1 p.m. - Server Shuffle – At the footbridge. The region’s top-notch wait staff race across carrying a cocktail tray with a beverage(s) and napkins.
2 p.m. – Tug of War Across the Harbor – Teams sign up for tugs in the footbridge parking lot and across the bridge to an east side lot.
4-5:30 p.m. - Mysterious Harbor Tours: Spooks & Spirits Walking Ghost Tour - Stories of UFOs over Boothbay Harbor to haunted locations. Tour ends on a spirited note at the Neat Whiskey Bar. FMI/Tickets: https://mysteriousharbortours.com/
7 p. m. American Ghost Walks - Hear pirate legends, about ghosts guarding their buried treasure; and local accounts of the three major types of ghosts. By reservation only: https://www.americanghostwalks.com/
7:30 p.m. - Lucy Wainwright Roche and Suzzy Roche – Opera House, 86 Townsend Ave. Advance discounted tickets $25 through the box office at 86 Townsend Ave. Wednesday – Friday 10 a.m. – 2 p.m. or call 633-5159. Regularly priced tickets $30 at https://boothbayoperahouse.com/
