Why You Need to Attend This Year’s Boothbay Harbor Windjammer Days

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 the celebration of the 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 a 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.

Get Your Free Guide!

What Is the Boothbay Harbor Windjammer Days Festival?

The history of Windjammer Days 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 century. 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.

Attend Windjammer Days 2019

The 57th Annual Windjammer Days Festival takes place June 23 – June 29, 2019. This year’s schedule features a wide range of events and attractions taking place all week long! Check out the intriguing Antique Boat Parade, meander around Artist’s Alley, indulge in the Crab Cake Cookoff, and stay for the fireworks 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 | June 23

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 Fleet is a beloved tradition that takes place at the beginning of each Boothbay Harbor Windjammer Days and is performed at Fisherman’s Memorial Park at 1:30 p.m.

Fireworks Over the Harbor | June 26

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 witness the sky light up over the majestic masts of the windjammers.

Antique Boat Parade | June 27

Over 40 antique boats will grace our harbor during the Antique Boat Parade at 3:00 p.m. Witness some of the most unique boats of many varieties as they sail through the harbor. We recommend watching from the deck of Coastal Prime Seaside Dining where you’ll enjoy music, cocktails, and boat tours during a post-parade reception.

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!