Windjammer Days in Boothbay Harbor: A Week of Tall Ships and Tradition

Every year in the last week of June, the windjammers come to Boothbay Harbor. They've been coming for 64 years now, and the festival that greets them — Windjammer Days — has grown into one of the most beloved maritime celebrations in New England.

Windjammer Days 2026 runs June 21–27, and it's the kind of event where the whole town turns out. It's not a boat show and it's not a regatta. It's something closer to a maritime homecoming — a week when Boothbay Harbor leans fully into its identity as a Maine harbor town and celebrates the tall ships that made the coast what it is.

The Ships

The centerpiece of Windjammer Days is the arrival and parade of the windjammers — Maine's fleet of historic schooners and tall ships that normally spend the summer carrying passengers on multi-day cruises along the coast. Watching them sail into Boothbay Harbor under full canvas, with crews lining the rails, is one of those moments that reminds you why people are drawn to the water in the first place.

Harbor tours are available during the festival, and some of the windjammers open their decks for visitors. If you've ever been curious about what it's like aboard a working schooner — the rigging, the galley, the narrow berths below deck — this is your chance to find out without committing to a full cruise.

The Festival

Windjammer Days is a full-week affair, and the programming goes well beyond the ships. The schedule includes four parades (land and sea), live music throughout the week, a waterfront concert, fireworks, a tug-of-war across the harbor, a road race, kids' activities, and food from local vendors and restaurants.

There's a pirate theme that runs through parts of the festival — mostly for the kids, but it adds color and energy to the street scenes. The downtown waterfront becomes an open-air gathering space for the week, and the atmosphere is equal parts community fair and nautical celebration.

Why Sailors Love It

If you sail, Windjammer Days is a pilgrimage. The chance to see Maine's traditional schooner fleet up close — not at a museum dock, but actively sailing in and out of a working harbor — is increasingly rare. These are living vessels with active sailing seasons, and the festival is one of the few times they're all in the same place at the same time.

For boat owners, Boothbay Harbor is a natural cruising destination with good anchorage and marina access. Arriving by boat during Windjammer Days puts you right in the middle of the action, and the harbor is lively in a way it isn't during a normal week.

Getting There and Getting Around

Boothbay Harbor is about an hour north of Portland via Route 1 and Route 27. Parking in town can be tight during the festival, especially on parade days and weekends. There's overflow parking at the Boothbay Railway Village and other outlying lots, with shuttle service into town on the busiest days.

If you're coming by boat, moorings and slips are available in the harbor and at nearby marinas, but reserve early — Windjammer Days is the busiest week of the year for Boothbay's waterfront.

The festival is a walking event once you're in town. The harbor, downtown shops, restaurants, and most event venues are all within a few blocks of each other. Wear comfortable shoes and expect to be on your feet.

Making the Most of the Week

Windjammer Days is best experienced over at least two or three days. One day gives you the parade and the waterfront, but spreading it out lets you catch the variety — a concert one evening, a harbor tour the next morning, the tug-of-war one afternoon. The midweek days are less crowded than the weekend, which can make for a more relaxed visit.

Boothbay Harbor itself is a worth a visit beyond the festival. The Coastal Maine Botanical Gardens are nearby, and the town has a strong restaurant scene for its size. If you're combining Windjammer Days with other Maine travel, it pairs well with a trip up Route 1 to Rockland or Camden.

Windjammer Days 2026 runs June 21–27 in Boothbay Harbor. For the full schedule and event details, check the listing on Meet Me at the Fair.