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Windjammer Days unfurls its sails each year in the last week of June, transforming Boothbay Harbor, Maine, into a vibrant celebration of majestic tall ships and rich maritime heritage. This annual festival provides ancient boat lovers with a fun way to begin their summer, offering everything from maritime tours to antique boat parades and lively shore-side music. Join the Blessing of the Fleet, explore historic vessels, and immerse yourself in nautical traditions.
Want to sponsor Windjammer Days? Learn how
Expected Windjammer Days Deals
As Windjammer Days approaches, local businesses in Boothbay Harbor and surrounding Maine coastal towns typically roll out special offers. Expect maritime-themed restaurants to feature fresh seafood specials, while boutiques might offer discounts on nautical apparel and gifts. Tour operators often provide special rates for boat excursions and harbor cruises during the festival week. Keep an eye out for deals from Maine Windjammer Association members and local inns. We will update this page with confirmed live deals as June 2027 approaches.
Platform Guide for Windjammer Days
Tag @nationaltoday_ and use #WindjammerDays to share stunning photos and videos of the tall ships, parades, and harbor festivities. Capture the beauty of Maine’s coast.
Mention National Today (facebook.com/nationaltoday) and use #WindjammerDays. Share event schedules, live updates from Boothbay Harbor, and invite friends to join the celebration.
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Mention @NatlToday and use #WindjammerDays for real-time updates on ship arrivals, parade routes, and live music performances. Engage with fellow maritime enthusiasts.
Windjammer Days Hero
Captain J.S. Winslow
History of Windjammer Days
We only had one form of transportation before motorways, motor vehicles, and the interconnected world — ships. These ships not only transported people, but they were also the only means of transporting products to other parts of the world.
The windjammer — our ancient sailing ship — was of a very specific category. With square-shaped towering sails — three to five to a ship — these vessels could glide over the water effortlessly. They also had loads of space in them to carry a larger amount of goods. The windjammers’ high utility and cargo capacity made them perfect to transport low-priced goods like food grains and fertilizers to ports of extreme hardship. While the commercial marine industry mostly ignored these ships, they retained their popularity among a smaller section of tradesmen.
Then, in the 19th and 20th centuries, modern steamships came around and stole everyone’s spotlight. Sailing ships not powered by motors didn’t have much use and began to be scuttled.
This was when an ex-navy man named Frank Swift turned the tide and introduced a whole region to leisure sailing on windjammers. Attracted to the older sailing ships since he was a little boy, Swift only hit upon the idea of windjammer sailing for people on a trip to Maine after seeing derelict coasting schooners in the harbors. Instead of scuttling them, he wanted to refurbish the vessels and carry vacationers back and forth. And so, with a little help from his sailing friends, Swift began to offer special passenger cruises on windjammers, continuing operations for 25-odd years even as cargo schooners were being replaced with modern sailing vessels everywhere else.
Windjammer Days timeline
Steam-powered modern vessels are much faster and easier to manage; they successfully replace the sailing vessels of that era.
The first official passenger cruises begin in Maine, with three lady passengers on board.
Frank Swift’s passenger cruises now have an extra load — the vessels transport pulpwood to paper mills to help in increased paper production.
This entire week — and related events — are organized by the nonprofit community organization Friends of Windjammer Days.
How Businesses Can Celebrate Windjammer Days
Local businesses in Boothbay Harbor can fully embrace Windjammer Days by offering maritime-themed specials and experiences. Restaurants can feature ‘Captain’s Catch’ seafood menus or nautical cocktails. Retailers can curate collections of local artisan crafts, sailing gear, or Maine-made products. Waterfront businesses can host special viewing parties for the parades, while tour operators can run themed excursions, perhaps even offering discounts to festival attendees. Boldly promote your connection to the sea and the community spirit.
Windjammer Days FAQs
When is Windjammer Days?
Windjammer Days in 2027 is scheduled for Sunday, June 27, through Saturday, July 3, inviting visitors to experience the beauty and history of Maine’s historic windjammer fleet. Plan your visit to Boothbay Harbor for this nautical celebration.
How many windjammers sail in Maine?
The Maine Windjammer Association typically maintains a fleet of about a dozen historic tall ships, offering multi-day cruises along the coast. These vessels are a living testament to Maine’s rich seafaring past and are the stars of Windjammer Days.
How many visitors attend Windjammer Days?
The popular festival attracts a substantial crowd, with its unique blend of historic ships, live entertainment, and community events. Local officials and organizers consistently report strong attendance, making it a highlight of Maine’s summer calendar.
What is a windjammer?
Historically, windjammers were commercial sailing ships used in the late 19th and early 20th centuries. Today, the term often refers to the historic tall ships that offer passenger cruises, preserving the tradition of sailing under canvas.
Windjammer Days Activities
Celebrate the sea and sailing
If you love the water, learning to sail is the perfect summer pastime for you. Search for classes near you, and get friends involved too. You could also explore different water sports and activities taking place in your surroundings. If none of this is possible, simply head to the closest water body (real or even man-made) and spend some time enjoying the view.
Learn all you can about windjammers
These ancient sailing ships have a unique and long history. Read all you can about these vessels, or check out a few documentaries and movies that have been made on this subject.
Participate in the Windjammer Days Festival
Kickoff your summer by taking a trip to Maine for the Windjammer Days Festival. Have fun watching the various sailing events and participating in different shore-side activities.
5 Windjammer Facts To Float Your Boat
What's in a name?
The word 'windjammers' was initially used in a derogatory manner by steamship sailors to mock the bigger and slower sailing ships.
They don't have just one name
Windjammers are also sometimes referred to as 'tall ships' because of their height.
Windjammers get recognized
Most of the windjammers from the Maine Windjammer Association — the largest group of sailing schooners in America — are officially designated as National Historic Landmarks.
Windjammers are big on sustainability too
The J&E Riggin won the Maine DEP Environmental leadership award in hospitality in 2007, the first windjammer to ever do so.
Windjammers need a little assistance too
Windjammers run on wind power alone, so if there's no wind, they use a little gas-powered boat rigged behind the ship for assistance while moving.
Why We Love Windjammer Days
It sparks a passion for the sea
The more we learn about these high-sea warriors, the more we are inspired to keep celebrating windjammers and the sea year after year.
Windjammers are the best
The ships themselves look very majestic sailing up and down Maine's rivers. Plus, these guys are an incredibly sustainable way to travel, with the windjammer not even using any motor or gas most of the time.
Flashback to the good old days
Remember when travel was not as fast and people could relax and take their time enjoying the sights? It is a callback to a simpler and calmer era of travel, which turns into the ultimate vacation for today's fast-paced world.
Windjammer Days dates
| Year | Date | Day |
|---|---|---|
| 2026 | June 21–27 | Sunday–Saturday |
| 2027 | June 27–July 3 | Sunday–Saturday |
| 2028 | June 25–July 1 | Sunday–Saturday |
| 2029 | June 24–30 | Sunday–Saturday |
| 2030 | June 23–29 | Sunday–Saturday |
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