Windjammer Days is the kickoff of the summer season in Boothbay. Neighbors and tourists gather to celebrate the rich maritime history of the area. The 61st annual weeklong event is Sunday, June 25 through Saturday, July 1, 2023. There are fun activities every day. If you cannot stay the entire week, here are some highlights for each day to help you plan your Windjammer experience.
The Schooner Isaac H. Evans offers sunset sails with a lobster bake on multiple evenings during Windjammer Days.
Sunday, June 25
1:00 pm Fun Sail – Sailboats less than 30 feet race each other on three circuits around the harbor. Watch the fun from shore.
1:30 pm Blessing of the Fishing Fleet – Commercial fishing vessels parade through the harbor. Everyone prays for the safety of all who make a living on the water.
8:30-10:00 pm Harbor Aglow – Lights adorn boats in the harbor with a parade that starts at 9:00 pm. This year, the 207-foot Oliver Hazard Perry will be magnificently lit and docked in the harbor.
Monday, June 26
1:00-3:00 pm Crab Cake Cook Off – Local chefs compete for the best use of Maine waters crabmeat. A celebrity panel will award bragging rights to the winner. Help support Windjammer Days at this ticketed event.
3:30-5:00 pm Boothbay Maritime Explorers Meet and Greet – Members of the community ranging in age from 23 to 83 were nominated by the committee. These adventurous people have sailed the waters of Maine and beyond.
Tuesday, June 27
Tuesday is full of activities for wee pirates including a puppet show at 10:00 am, cannon lessons at 11:30 am and 4:00 pm, and recruitment of young pirates at 3:00 pm.
Wednesday, June 28
12:00 pm Pirate Battle – The activities for kids continue with a high noon battle against the British.
12:30 pm Lobster Eating Contest – Watch ten participants compete to eat 1 ½ pound lobsters. The first contestant to finish eating two lobsters will win a $100 prize.
2:00 pm Cod Fish Race – Ten teams of four sprint in a relay race around a course while carrying two slippery fish. Each teammate must also pass along their attire of fisherman’s oilskins and boots. This is one of the funniest “sporting” events you will ever see.
4:00 pm Street Parade – Boothbay is very proud of its maritime history and its sense of community spirit. Find a spot on the sidewalk along the parade route to be an honorary member of the community.
9:00 pm Fireworks – The towering masts of the windjammers add extra beauty to this fireworks show over the harbor.
Thursday, June 29
7:00 – 11:00 am Windjammer Fleet Leaves the Harbor – While not an official boat parade, it can feel like one. Sit on the shore and watch as each of the majestic boats leaves Boothbay Harbor.
9:00 am – 5:00 pm Artist’s Alley – Venture over to Whale Park for art demonstrations and sales. The 2022 festival had 19 local artists showcasing jewelry, woodwork, fine art, pottery, sculptures, and windchimes.
9:00 am – 12:00 pm Farmers’ Market – The weekly market continues during the festival with locally produced food and products from local artisans.
12:00 pm International Rock Skipping Contest – Join for $5 or just watch the fun. Winners in four divisions will each receive a Windjammer Days t-shirt and one pound of fudge from Orne’s Candies. Adult winners will also receive pottery by AE Ceramics or a gift certificate from Footbridge Brewery.
12:30 pm Tug of War Across the Harbor – Head to the footbridge in the center of town for the best view of this 700-foot tug of war contest. Friends and family will stand on the East and West side of the harbor as they pull their way to victory. The Chowder House hosts a viewing party for the rock skipping contest and tug of war.
Friday, June 30
9:00 am – 5:00 pm Artist’s Alley continues.
4:00 – 7:00 pm Vintage Boat Parade and Pier Party – A fleet of boats 25 years and older parade around the harbor at 4:00. The parade is free to watch. After the parade, the vintage boats dock at The Shipyard for the after party. The ticketed party will have appetizers, a full bar, and live music.
7:30 pm Oshima Brothers at the Boothbay Opera House – The nationally touring musicians combine unusual sounds such as a fiddle with an R&B groove or an acoustic ballad with an electronic beat.
Saturday, July 1
9:00 am Kayak Poker Run – Kayaks will stop at seven stops in the harbor to pick up a playing card. Prizes will go to the team that finishes first and the team with the best poker hand.
1:00 pm Classic Sailboat Race – Monohull sailboats designed before the year 2000 will compete for prizes.
