Boothbay Harbor, Maine - The 60th annual Boothbay Harbor Windjammer Days sails in tomorrow from June 26th - July 2nd, 2022, in Boothbay Harbor, Maine.
Windjammer Days marks the kickoff to summer in the Boothbay region and is
a time to reconnect with family, friends and neighbors after the long winter, an opportunity to support local businesses and welcome visitors. It is a time to honor our maritime history and celebrate the vital role it plays in the lives of all who live here.
Several Windjammers will be docked or anchored in the harbor for this wonderful summer event
Full Schedule:
SUNDAY, JUNE 26, 2022
10:30 AM - 12:00 PM
Stories from the Sea & Sea Shanties
with musical guest Castlebay
Merry Barn, Edgecomb
1:00 PM
Boothbay Harbor Yacht Club Windjammer Days
Fun Sail
1:30 PM
Blessing of The Fleet
6:30 PM
Sunset Cruise and Lobster Bake
Two hour cruise aboard Schooner Isaac H. Evans and lobster bake back at the dock of The Shipyard
7:00 PM - 8:30 PM
Red Cloak Haunted History Tour
Expand your knowledge of the supernatural with local accounts (by reservation only)
8:30 PM - 10:00 PM
Harbor Aglow
Docked boats light up around the harbor from 8:30-10:00 PM. Lighted Boat Parade starts at 9:00 PM and circles the harbor.
MONDAY, JUNE 27, 2022
1:00 - 3:00 PM
4th Annual Windjammer Days Crab Cake Cook Off
Boothbay Harbor Inn
4:00 PM - 5:00 PM
Ernestina-Morrissey Talk
The Shipyard at Bristol Marine
6:00 PM
Boothbay’s Got Talent
6:30 PM
Sunset Cruise and Lobster Bake
Two hour cruise aboard Schooner Isaac H. Evans and lobster bake back at the dock of The Shipyard
TUESDAY, JUNE 28, 2022
7:00 AM - 10:00 AM
Pancake Breakfast
Whale Park
9:00 AM - 5:00 PM
Friends of Windjammer Days Tent Open Information available. Raffle tickets with prizes every hour!
10:00 AM - 1:00 PM
Kids Alley
Boothbay House Hill across from Two Salty Dogs
10:00 AM – 10:30 AM
Pirates of the Dark Rose Puppet Show
Whale Park
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
11:00 AM - 1:00 PM
Pirate Ship Must Roos Tours
Whale Park Public Landing
11:30 AM
Crudbeard’s Cannon Lessons
Whale Park
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
6:30 PM
Sunset Cruise and Lobster Bake
Two hour cruise aboard Schooner Isaac H. Evans and lobster bake back at the dock of The Shipyard
WEDNESDAY, JUNE 29, 2022
7:00 AM - 10:00 AM
Pancake Breakfast
Whale Park
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
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 - 3:00 PM
Kids Tent Activities
Boothbay House Hill across from Two Salty Dogs
10:00 AM - 11:00 AM
Pirate Ship Must Roos Ship’s Rail Open
Whale Park Public Landing
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
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
6:00 PM
New England Wooden Boat Preservation Dock Party
Enjoy boat tours and a floating oyster bar aboard the Schooner Isaac H. Evans
7:00 PM - 8:30 PM
Red Cloak Haunted History Tour
Expand your knowledge of the supernatural with local accounts (by reservation only)
THURSDAY, JUNE 30, 2022
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
Artist’s Alley
Whale Park
9:00 AM - 12:00 Noon
Boothbay Farmer’s Market
Boothbay Common
1:00 PM
Windjammer Days Golf Tournament
Boothbay Harbor Country Club
4:00 PM
Annual Antique Boat Parade & Pier Party
Watch the parade circle the harbor then view them up close at The Shipyard for the after party
4:30 PM - 7:00 PM
Antique Boat Parade & Pier Party
The Shipyard in Boothbay Harbor
7:00 PM - 8:30 PM
Red Cloak Haunted History Tour
Expand your knowledge of the supernatural with local accounts (by reservation only)
FRIDAY, JULY 1, 2022
9:00 AM - 5:00 PM
Artists Alley
Whale Park
11:00 AM
18th Annual Orne's Candy Store International Rock-Skipping Contest (in memory of Arthur Webster)
Benefit of the Boothbay Region Health Center
11:00 AM - 2:00 PM
Chowder House Spectator Party
22 Granary Way
12:00 PM
Tug of War Across The Harbor
Best viewing is from the footbridge in the center of town
6:30 PM
Sunset Cruise and Lobster Bake
Two hour cruise aboard Schooner Isaac H. Evans and lobster bake back at the dock of The Shipyard
Saturday, July 2, 2022
9:00 AM
Kayak Poker Run
Kayakers paddle around the inner harbor and pick up cards at each dock. Open to the public.
1:00 PM
Boothbay Harbor Yacht Club Classic Sailboat Race
7:30 PM
Louis Prima, Jr & The Witnesses
the Opera House at Boothbay Harbor
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