Harpswell’s History from Sea to Shining Shore!

June 12, 2026

(Photo-Courrier-McEwen-family)-E.-Farrington-Abbott-family-in-its-chauffeur-driven-car-in-1916

Ready to enjoy a summer day sailing along Harpswell’s distinctive shoreline on a beautiful schooner?

Join us for half a day of sailing and storytelling about Abenaki natives to today’s newcomers. Step back in time on a wooden fishing schooner and enjoy Harpswell history and lore as told by The Brothers YorkRon York, storyteller, former postman and Harpswell original and his brother, Gerry York, historian and administrator of Harpswell Yesterdays. The York family has graced Harpswell shores for many generations, and these two men know the ins and outs of the properties, the families and the long-told tales—some of which are actually true!

When: Sunday, August 9 and Monday, August 10 from 10:30 am to 2:30 pm (rain date: August 11, same time)

Where: Alert at Cook’s Lobster Dock, Garrison Cove Road, Bailey Island

Cost: $75/person (20 person limit per trip. Your payment holds your reservation. Bring your own lunch.)

Sponsored by: Harpswell Historical Society, 250th Committee and Harpswell Islands Genealogy and History Center

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FAQs

Where do I park? You can park in Cook’s Lobster and Ale House Restaurant parking lot at the North End of Garrison Cove Rd. on Bailey Island. Please park at the most north end or south end of their (as far from the restaurant entrance as practical).

How long is the trip? Four hours. Depending on weather and wind conditions, we will see Bailey Island, Orr’s island, the eastern part of Harpswell Neck and several of the Calendar Island and you will hear tales of each area. Please arrive by 10:15 am

Is there a bathroom on board? Yes on the lower level, accessible by a companionway ladder.

What about food and drink? You can bring anything you like to eat or drink on the boats. Adults who are 21 years and older may being alcoholic beverages. No food will be for sale on the boat.

What should I bring? Bring an extra layer to keep you warm while on the water, plus a sun hat, sunscreen and sunglasses. Binoculars and a camera are nice to have. Please no cleats or high-heeled shoes.

Motion sickness? Generally we are in protected waters, and motion sickness is not a big issue. Please plan ahead and bring medication if you are prone to motion issues.

Questions: Call Lili at 207-833-3398 or Bethany at 207-841-9125

About the schooner Alert

Alert is 56 feet on deck, 70 feet over all and was built in 1992 by Paul Rollins in York, Maine.

Alert’s original name was Tall Cotton. In 2006 Roger Woodman, a fisherman, restored the boat to long line for fish offshore and renamed her Alert. In January 2013 Perry and Bethany bought Alert and in September 2013 completed the boats testing and documenting with the United States Coast Guard to bring her into the passenger trade. Today they are hosting public sails and Private charters on Alert Daily.

Home port: Bailey Island, Maine

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