2025 Windjammer Days event schedule
The 63rd year!
EVENTS CALENDAR
All events held in Boothbay Harbor unless otherwise noted
The Friends of Windjammer Days tent is open Tuesday, June 24 from 9 a.m. to 5 p.m. and Wednesday, June 25 from 9 a.m. to 9 p.m. Raffle tickets, information, signup for contests, raffle drawings every hour both days
SUNDAY, JUNE 22
9 a.m. - 4 p.m. - R/C sailing competition at Spruce Point Inn (SPI) - SPI and Maine Model Yacht Club (MMYC) host a day of R/C sailing competition and spectating at the Spruce Point Inn dock and oceanside pool. 88 Grandview Ave. SPI Cup awarded at 5 p.m. 88 Grandview Ave.
10 a.m. – noon – Hidden Harbor E-Bike Tour – The road less traveled leads to mysterious locations with Pedego Bikes, Meadow Mall. FMI/tickets to ride: https://mysteriousharbortours.com - advance purchase required.
1-3 p.m. – Joy E-Bike Tour – With Pedego Bikes. Ride through the beauty of the peninsula with a stop at Villard Studios! FMI/tickets to ride: https://mysteriousharbortours.com/ - advance purchase required.
1:30 p.m. - Blessing of the (Fishing) Fleet - By local clergy. Best viewing: on the water, Fishermen’s Memorial Park on Atlantic Avenue., and Whale Park.
4-5:30 p.m. – Mysterious Lore & More - Travel into Boothbay Harbor’s long and mysterious history. At Whale Park, Commercial Street. FMI/tickets to ride: https://mysteriousharbortours.com/ - advance purchase required.
6 p.m. - Boothbay’s Got Talent - Youth compete for the titles of The Royal Windjammer (ages 7-12) and The Top Royal (ages 13-18). Boothbay Region YMCA, 261 Townsend Ave.
7- 8:30 p.m. - American Ghost Walks Tour - Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.
MONDAY, JUNE 23
10-11:30 a.m. – Mysterious Lore & More - Travel deep into the heart of Boothbay Harbor’s long and mysterious history. At Whale Park, Commercial Street. FMI/tickets to ride: https://mysteriousharbortours.com/
1-2:30 p.m. – 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 to ride: https://mysteriousharbortours.com/
1-3 p.m. - 7th Windjammer Days Crab Cake Cook Off - Boothbay Harbor Inn, Atlantic Avenue. A ticketed event. Celebrity panel of judges. Advance purchase only at https://tinyurl.com/4kf2tyem
4-5:30 – Spooks & Spirits Walking Ghost Tour – Unveil Boothbay Harbor’s eerie side through goosebump-inducing stories – and a stop at Neat Whiskey Bar. FMI/tickets: https://mysteriousharbortours.com/
5 -6 p.m. - Meet & Greet with USCG Honorees – Come to Boothbay Harbor Oceanside Resort, 35 Atlantic Ave. to talk with Festival spotlight group.
6 p.m. - “How I Became a Pirate! The Musical!” - Performed by members of the Y Arts program at the Opera House, 86 Townsend Ave. 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. General admission $10.
7- 8:30 p.m. - American Ghost Walks Tour - Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.
TUESDAY, JUNE 24
7-9 a.m. - Pancake Breakfast - Whale Park, Commercial Street
9 a.m. – 5 p.m. - Pirate Coin Forging - Whale Park
10–10:30 a.m. – Pirate Puppet Show – Featuring an unusual cast of characters, Whale Park, Commercial Street
10 a.m. – Noon - Hidden Harbor E-Bike Tour - The road less traveled leads to some mysterious locations! With Pedego Bikes, Meadow Mall. FMI/tickets to ride: https://mysteriousharbortours.com/
10 a.m. - 1 p.m. - Kids Alley – Games, crafts, and more! Whale Park, Commercial Street
10 a.m. - 1 p.m. - Windjammers for Wee Mateys - Ocean-themed crafts, lawn games, and more. Boothbay Harbor Memorial Library lawn, 4 Oak St.
11 a.m. - 1 p.m. - Pirate Tortuga - bazaar with games and activities in Whale Park
11:30 a.m. – Cannon Lessons - With the Pirate Crudbeard - Whale Park
1-2:30 p.m. – Paranormal Pedal E-Bike Tour - 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! At Pedego Electric Bikes. FMI/tickets to ride: https://mysteriousharbortours.com/
1:30 p.m. – Hot Dog Eating Contest – NEW EVENT! Whale Park. Two heats: one for kids, one for adults. Prizes for first, second and third places. $10 entry fee. FMI: duntonsdoghouse@gmail.com
2 p.m. - Pirate Weapons Demonstration – Whale Park
3 p.m. - Recruitment of Young Pirates – Whale Park
4 p.m. - Cannon Lessons - With the Pirate Crudbeard - Whale Park
4-5:30 p.m. - 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 to ride: https://mysteriousharbortours.com/
5 p.m. - “How I Became a Pirate! The Musical!” - Performed by members of the Y Arts program at the Opera House, 86 Townsend Ave. 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. General admission $10.
7- 8:30 p.m. - American Ghost Walks Tour - 22 Granary Way. Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.
WEDNESDAY, JUNE 25
7 – 9 a.m. - Pancake Breakfast – Whale Park
9 a.m. – 5 p.m. - Pirate Coin Forging - Whale Park
10 a.m. - 3 p.m. - Maine State Aquarium Activities - Explore how lobsters grow and who the Department of Marine Resources scientists are who study them. The aquarium experience includes a variety of tanks, hands-on exhibits and interactive displays, and make lobster crafts. McKown Point Road, W. Boothbay Harbor.
10 – 11 a.m. - Pirate Tortuga - bazaar with games and activities in Whale Park
10:30 a.m. - Pirate Crudbeard’s Cannon Lessons - Whale Park
12 Noon - Windjammer Days Photo Cruise - With professional photographer Mike Leonard aboard the Balmy Days departing from Pier 8. Don’t forget your camera! Tickets: Balmy Days Cruises: 207-633-2284 or https://balmydayscruises.com
12 Noon – The Battle For Boothbay Harbor – Live cannon fire! Whale Park
12:30 p.m. - Lobster Eating Contest – Openings for 10 competitors. Sign up at Friends of Windjammer Days Tent on the waterfront
1-3 p.m. – Gathering of the Fleet - Visiting and local schooners arrive in the Harbor
2 p.m. - Fish Relay Races – Teams sign up at the Friends of WJD tent in Whale Park. Racing on Commercial Street
2-3 p.m. - Pirate Tortuga - Games and activities in Whale Park
4 p.m. - Street Parade! Event begins from schools parking lot on Townsend Avenue and proceeds to the downtown area/Commerical Street.
7- 8:30 p.m. - American Ghost Walks Tour - 22 Granary Way. Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.
9 p.m. - Fireworks!
THURSDAY, JUNE 26
9 a.m. - 5 p.m. - Artists Alley – Art, jewelry, pottery and more … a treasure trove of creativity.
10 a.m – noon - Hidden Harbor E-Bike Tour – The road less traveled leads to some mysterious locations! With Pedego Bikes, Meadow Mall. FMI/tickets to ride: https://mysteriousharbortours.com/
10 a.m. - 3 p.m. - US Coast Guard Station Tours - 166 McKown Point Road, West Boothbay Harbor.
1-3 p.m. - Paranormal Pedal E-Bike Tour - 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! At Pedego Electric Bikes. FMI/tickets to ride: https://mysteriousharbortours.com/
4-5:30 p.m. - Spooks & Spirits Walking Ghost Tour – Unveil Boothbay Harbor’s eerie side through goosebump-inducing stories – and a stop at Neat Whiskey Bar. FMI/tickets: https://mysteriousharbortours.com/
7 - 8:30 p.m. - American Ghost Walks – Expand your knowledge of the supernatural with local accounts (by reservation only). Visit www.americanghostwalks.com/maine for tickets and information.
FRIDAY, JUNE 27
9 a.m. - 5 p.m. - Artists Alley – In Whale Park. See June 26 listing for details.
10 a.m. – noon - Hidden Harbor E-Bike Tour – The road less traveled leads to some mysterious locations! With Pedego Bikes, Meadow Mall. FMI/tickets to ride: https://mysteriousharbortours.com/
4 p.m. - Vintage Boat Parade – Antique boats of all sorts parade around the Harbor. Best viewing: On the water or anywhere around the inner harbor.
4:30 - 7 p.m. – Pier Party at the Shipyard – Admire antique vessels, cars and motorcycles at Bristol Marine Shipyard on Commercial Street and join the Pier Party. Tickets required. Buy at www.boothbayharborwindjammerdays.org
7 p.m. - "RED" - A Boothbay Summer Theater production. Abstract expressionist artist Mark Rothko battles his demons in this Tony Award-winning play. 7 p.m. At Boothbay Railway Village Museum, 586 Wiscasset Road, Boothbay. Tickets, $25, at https://boothbaysummertheater.com/
7- 8:30 p.m. - American Ghost Walks Tour - Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.
7:30 p.m. – I Draw Slow – A roots five-piece band from Ireland. Opera House, 86 Townsend Ave. Tickets: Advance discounted $25 only through the box office in person – open Wednesday – Friday from 10 a.m. to 2 p.m. or call 633-5159. Regularly priced tickets $30 at https://boothbayoperahouse.com
SATURDAY, JUNE 28
10 a.m to noon: Hidden Harbor E-Bike Tour – The road less traveled leads to some mysterious locations! With Pedego Bikes, Meadow Mall. FMI/tickets to ride: https://mysteriousharbortours.com/
11 a.m. - 4 p.m. – The Boat Bar Party - Chowder House, 22 Granary Way. A ticketed event - $27.50. Visit https://t.ly/FU1O1 to buy a ticket that includes select appetizers. Cash bar. Watch Tug of War, Rock Skipping and Server Shuffle from here!
11 a.m. - 1 p.m. - 20th Orne's Candy Store International Rock Skipping Contest - Signup begins at 11 a.m. Stones fly at 11:30. Sweet prizes! A benefit for Boothbay Region Health Center and Maine Lobstermen’s Association.
2 p.m. - Tug of War Across the Harbor - Teams of eight to 10 compete for the Loving Cup and braggin’ rights. At the Footbridge parking lot. Best viewing: the Footbridge
1-3 - Paranormal Pedal E-Bike Tour - 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! At Pedego Electric Bikes. FMI/tickets to ride: https://mysteriousharbortours.com/
1 p.m. - Server Shuffle - Second year! Local wait staff race while carrying a bar tray with drinks ... without spillage. At the Footbridge. FMI/signup: www.boothbayharborwindjammerdays.org
4-5:30 p.m. - 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 to ride: https://mysteriousharbortours.com/
7 p.m. - Decorating Boat Parade - NEW! - Decorated boats, many with a theme, will be on display while docked prior to the start of the parade at 7. Route begins on the east side of the Harbor just before Tugboat Inn. Vessels will circle around the Harbor twice.
7 p.m. - "RED" - A Boothbay Summer Theater production. Abstract expressionist artist Mark Rothko battles his demons in this Tony Award-winning play. 7 p.m. At Boothbay Railway Village Museum, 586 Wiscasset Road, Boothbay. Tickets, $25, at https://boothbaysummertheater.com/ Tickets, $25, at https://boothbaysummertheater.com/
7- 8:30 p.m. - American Ghost Walks Tour - Expand your knowledge of local supernatural lore. By reservation only. Visit www.americanghostwalks.com/maine for tickets and information.