We’re not too proud to brag, Bailey Island boasts a one-of-a-kind landmark

Our island communities have rich histories—from WWII fortifications on Peaks Island to a one-of-a-kind bridge on Bailey Island—we always love bragging about the bay we call home.

Bailey Island, a part of the town of Harpswell for over 250 years, sits at the farthest end of one of our most popular summer cruises. People from away (and their Maine friends!) love grabbing a lobster roll at the famous Cook’s Lobster & Ale House once they arrive. And we dream about the relaxing, sun-soaked cruise to this fantastic spot all winter long while we’re braving Casco Bay blizzards.

The story of how Bailey Island, originally called Newaggin by the local Abenaki tribes, was first settled is a topic the historians and locals debate. What we do know for sure is that the island’s namesake, Rev. Timothy Bailey, settled on the island in 1742, and the rest is history.

In the late 1800s, Bailey Island residents wanted a way to connect with the mainland, so a bridge between Bailey Island and neighboring Orr’s Island was proposed. Cost and U.S. involvement in WWI meant construction didn’t begin until 1927.

According to the Harpswell Historical Society, Maine architect Llewellyn N. Edwards and his team finished constructing the Cribstone Bridge in 1928. Made of individual granite ties in a crisscrossing framework, the bridge has stood strong against the power of the tides – with little to no maintenance – for close to 90 years!

Even cooler though – this bridge on Bailey Island is the only one of its kind in the world! Rumor has it Scotland may have one too. But with no record of its existence, Maine holds on to bragging rights for now.

Want to check out Bailey Island for yourself? Our Bailey Island Cruise leaves the dock in Portland at 10 a.m. daily through Labor Day. When the boat arrives on the island, you’ve got two hours to explore. We’d recommend heading to Cook’s for an order of steamers or bringing a picnic lunch to eat while you watch the waves at one of the nearby beaches. If you want more time on the boat, we also offer a noontime cruise through Potts Harbor, past Eagle Island, and peeking into Mackerel Cove.

If you’re feeling really adventurous, buy a one-way ticket and bring your bike along for a gorgeous coastal ride back to Portland – it’s just over 45 miles once you cross that incredible bridge.

Stop by our terminal or check out our website for more information.