Windjammer Days is a lively celebration where elegant tall ships sail into Boothbay Harbor’s calm waters. The day bursts with energy as colorful vessels glide in and gather off Cabbage Island.
Crowds line the shore, cheering and snapping photos as sails unfurl and boats drift under bright skies. That harbor entrance feels like a page turning in a living story—everyone leans forward, and for a moment, time pauses.
What follows spreads warm togetherness through the town. Neighbors greet each other with waves and laughter.
Boats anchor, crews mingle with visitors during clambakes and tours, and jugglers or musicians pop up by the water’s edge.
The harbor hums with life—kids race skipping stones, friends toast with cider, and tourists stay to share smiles.
That moment marks summer’s start, when the community pulses with maritime pride and simple joy that draws people back each year.
How to Celebrate Windjammer Days
Here are some fun and creative ways to dive into Windjammer Days:
Catch the Gathering
Board a cruise boat to see tall ships sail into the harbor under full sail. Captains narrate landmarks like Burnt Island Light and Ram Island Light. The best view lies on open decks.
Cheer the Friendly Contests
Take part in tug-of-war, rock‑skipping, crab‑cake or hot‑dog contests. Watch teams compete across the harbor or beside the pier. Events spark smiles for all ages.
Stroll Food and Art Booths
Wander through Artists Alley and food tents near Whale Park. Sample local seafood or sip craft brews. Catch street music and meet regional artisans.
Join Pirates and Parades
Watch costumed pirates perform lively shows for kids. Then roam the vintage‑boat parade or lighted‑boat show by night. Fun swirls through the harbor scene.
Experience Harbor Aglow
Stay after sunset to see illuminated boats drift by. Harbor Aglow pairs with fireworks to crown the evening. Lanterns glow softly across waves.
Enjoy Tours and Sightseeing
Join ghost walks, e‑bike treks, Coast Guard station visits, or harbor history tours. Guides share spooky tales or local lore on foot or by bike.
History of Windjammer Days
Windjammer Days began with a simple idea sparked by an unexpected sight. In 1962, Captains David and Marion Dash looked out at Boothbay Harbor and saw three tall ships resting in the fog.
Moved by that quiet scene, they decided to bring more windjammers to town the next year. They reached out to schooner captains sailing the coast, and the plan came together.
On July 10, 1963, the first Windjammer Days took place. Several ships arrived, sails up, flags flying.
Crowds filled the docks and cheered as the schooners entered the harbor. Captain Dash helped lead the early events, working with others to welcome both sailors and visitors.
Over the years, the celebration grew. Volunteers added music, street performers, fireworks, and more. In 2013, a local nonprofit called Friends of Windjammer Days stepped in to run the event. They helped expand it into a weeklong gathering, full of both land and sea traditions.
Today, people travel from across the country to see these ships and enjoy the harbor. Though the festival has changed, the heart of it remains the same.
Tall ships still sail in. Locals still wave from the shore. And the harbor still comes alive with stories, laughter, and sails.
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