Discover the Best Entertainment at the Boothbay Harbor Windjammer Days Festival

Before there were planes, trains, and automobiles, sailing ships were the best way to transport goods and travel the world. Learn about the unique history of American shipping, which dates back several centuries, at this year’s week-long Boothbay Harbor Windjammer Days. Participate in celebrating the Boothbay region’s rich maritime history while enjoying tons of events throughout the week, including parades, boat tours, live music, and more. There’s no better way to start your summer than with week-long trip to Boothbay Harbor to enjoy this thrilling festival! As you begin to plan your trip, be sure to request a copy of our complimentary Vacation Guide. Inside this handy vacation planner, you’ll discover dozens of great recommendations on restaurants, activities, and other local events. 

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What Is the Boothbay Harbor Windjammer Days Festival? 

The history of the Boothbay Harbor Windjammer Days Festival dates back hundreds of years when wooden ships raced up and down the eastern seaboard in hopes of being first to market with their goods. One of the most popular boats was the windjammer — a large sailing ship built to carry cargo in the 19th and early 20th centuries. Windjammers were the grandest of merchant sailing ships, with three to five large masts and square sails. Today, instead of carrying fish, granite, and lumber, these tall ships sail the bays of Maine, transporting guests to a bygone era. 

Can’t-Miss Events at The Annual Windjammer Days Festival 

The annual Windjammer Days Festival usually takes place in late June. The Windjammer Days Festival features a wide range of events and attractions that take place all week long! While you’re enjoying the festival, be sure to check out the intriguing Tall Ships Festival, meander around Artist’s Alley, indulge in the Crab Cake Cookoff, and stay for the breathtaking firework finale. You can also enjoy live music throughout the week, embark on boat excursions, participate in the street parade, or sign up for the lobster eating contest. Don’t forget to check out some of the most popular events.

Blessing of the Fleet  

Every year, residents and visitors gather in Boothbay Harbor to remember those who have lost their lives at sea. It’s also a great time to pray for the safety of those who still earn their living on the water. The Blessing of the Fleeis a beloved tradition that takes place at the beginning of each Boothbay Harbor Windjammer Days and is performed aFisherman’s Memorial Park 

Gathering of the Fleet 

Watch as the festival’s guests of honor make their grand entrance. Year after year, the treasured Windjammers gathenear Cabbage Island to start their trip into the Boothbay Harbor. This glorious sight can be seen from the east and west sides of the harbor at Whale Park, the Footbridge, Fisherman’s Memorial, and the Aquarium on McKown Point, among others.  

Cod Fish Relays 

Perhaps one of the most anticipated events of the festival Cod Fish Relay. Teams of four daring participants jump into fisherman’s oilskins and boots. Then they carry two slimy fish around a short courseThey pass the attire and the fish to the next teammate and so on until they complete the race. The team with the fastest timtakes home a $100 prize, and the spectators enjoy endless laughs!  

Antique Boat Parade 

Over 40 antique boats will grace our harbor during the Antique Boat Parade. Witness some of the most unique vintage boats as they sail through the harbor. We recommend watching from the deck of Boothbay Harbor Oceanside Golf Resort, where you’ll enjoy music, cocktails, and boat tours during a post-parade reception. 

Note: In 2021, the Antique Boat Parade is planned to occur, and Maine CDC COVID guidelines in June will determine the post-parade reception. 

Fireworks Over the Harbor 

When you stay at Topside Inn, you’ll have the best view of the spectacular fireworks display! You don’t even need to leave the property to enjoy this event, as many of our guests sit on the front lawn to see the sky light up over the majestic masts of the windjammers. 

Lighted Boat Parade 

From anywhere within the inner harbor, you can enjoy a parade like no other. The Windjammer Days Lighted Boat Parade invites boaters to fill the harbor with an array of intricate light displays. Each boat is decorated in colorful twinkling lights, and some even feature music, dancing, or singing!  

Enjoy Your Stay at Topside Inn

View of living area in the Suite at Topside Inn

The annual Boothbay Harbor Windjammer Days Festival is a favorite event enjoyed by both locals and visitors alike. If you’re planning to attend this year, make your reservations at the Topside Inn. Our bed and breakfast overlooks the harbor and offers top-notch accommodations and amenities. Just minutes from downtown, Topside Inn provides easy access to one of Boothbay Harbor’s most popular events.

During your stay, you can relax in the beautifully furnished Suite with an extra level of privacy. This recently renovated space features a fully equipped kitchen, a private front porch, and a large master bathroom with a soaking tub and glass shower. It’s perfect for relaxing after all the excitement.

Browse our complete collection of available accommodations and start planning your trip today!