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In October 2025, members of the Harpswell Historical Society had a discussion with town leaders and agreed to work together to plan a townwide celebration of the 250th anniversary of the signing of the Declaration of Independence.
Lili Ott, secretary of the Historical Society, reached out to dozens of community nonprofits, informal clubs and organizations to see if they wanted to participate in the celebration. The response was immediate and positive: an enthusiastic yes! The Girl Scouts, the Harpswell Garden Club, local historians, Revolutionary War reenactors, the libraries and many others volunteered to step up and make it happen.
One idea that was floated was a scavenger hunt or challenge encouraging participants to explore all parts of town, including Cundy’s Harbor, Great Island, Orr’s Island, Bailey Island and Harpswell Neck, all the way from North Harpswell down to the tip of South Harpswell. Hmm … that sounded like it could be a fun, family-friendly event. And since we were going to be celebrating 250 years of American history and Harpswell was incorporated 268 years ago in 1758, why not make it a historical scavenger hunt? That’s how the Harpswell History Hunt was born!
Katie Neal, Harpswell’s director of parks and recreation, had organized similar events in the past. She signed on with Cindy Bessmer, of Orr’s Island, to brainstorm the event. First, they had to identify easily accessible historical sites and secure permission to post temporary signage there.
A “treasure map” would be integral to the project, so Amelia Waszynski, communications specialist for the town, was enlisted to design the map, while Bessmer researched old postcards, pictures and historical notes. A “Harpswell History Hunter” pin was designed and ordered for all participants. The hunt came together as maps and placards were printed, ready to be strategically placed at 16 historical sites at the beginning of July.
Although the hunt can be completed in a single day, it doesn’t have to be. In fact, the History Hunt can be completed any time between July 4 and Aug. 31. It will be perfect for visiting grandchildren, history buffs from away or vacationers seeking a fun exploration of Harpswell.
Here’s how to play: Pick up a map and entry card at the Harpswell Town Office, Orr’s Island Library or Cundy’s Harbor Library during their regular business hours. Follow the map to each location, read the placard about its history, and record the secret code letter in the lower right corner of the placard. Once you have all 16 letters, unscramble them into a three-word phrase and add it to your entry form. Return your form to the Town Office or either library to receive a pin and a chance to win additional local prizes. Prize winners will be randomly chosen from all correct entries submitted by Aug. 31.
Celebrate America’s 250th birthday here in Harpswell. Happy hunting!
