A Maritime Celebration in the Heart of Boothbay

Boothbay Harbor comes alive each June with one of Maine’s most beloved summer festivals: Windjammer Days. Spanning over a week, this annual event (June 22–28, 2025) celebrates the region’s deep-rooted nautical traditions with an exciting lineup of tall ship parades, fireworks, races, live music, and more. It’s a true celebration of Maine’s maritime spirit, and a must-experience for families, couples, and history buffs.

The Parade of Sails

The star attraction of Windjammer Days is the Parade of Sails, when a majestic fleet of historic schooners enters Boothbay Harbor under full sail. Visitors line the piers and footbridge to watch these windjammers pass within feet of the shore, a breathtaking reminder of the golden age of sail.

You can even book a sailing trip aboard a schooner, such as the Eastwind or the Lazy Jack II, to join the parade on the water. These charters fill up quickly, so advance booking is recommended.

Local Food, Music & Festivities

In addition to the nautical events, Windjammer Days features:

• Live concerts on the waterfront

• A pirate-themed scavenger hunt for kids

• The hilarious Cod Fish Relay Race

• A lobster eating contest

• Dozens of local food vendors and craft booths

The event is community-run and family-friendly, offering a mix of free and ticketed experiences that highlight Boothbay’s charm and hospitality.

Full event schedule available at Windjammer Days Official Site

Fireworks Over the Harbor

Cap off the festivities with a stunning fireworks display over the harbor. Visitors and locals gather along the piers, lawns, and boats to watch the sky light up in celebration. It’s a magical way to end the week—and the perfect time to reflect on your Maine vacation.

Stay Close to the Action with Maineland Vacation Rentals

After a full day enjoying schooners, seafood, and small-town festivities, retreat to the comfort of your private coastal getaway with Maineland Vacation Rentals. Choose from a wide selection of vacation homes, waterfront cottages, and family-friendly properties just minutes from downtown Boothbay Harbor.

Whether you want to:

• Watch schooners pass from your deck

• Grill up some local lobster on your patio

• Walk to the footbridge for daily events

Maineland Vacation Rentals offers the perfect home base for your Windjammer Days experience. With thoughtfully appointed kitchens, cozy living spaces, and stunning harbor views, it’s easy to unwind and recharge for another day of coastal fun.

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