Why do we do It. Ask anyone participating in the hiking challenge why they do it and you will probably hear a wide range of responses. We do it to prove to ourselves that we have endurance. To make ourselves and others proud of our accomplishments. To test our navigation skills. To exercise and enjoy nature. But we can all agree—we do it because it’s a challenge.

Being part of and completing a hiking challenge requires a lot more than just personal motivation and stamina. What you don’t see is the number of people in the background who make it happen. Seamlessly and flawlessly. And like some of the trails, the journey to hosting a hiking challenge is neither short nor easy.

It takes a village. For the past 15 years (minus 2 years during COVID), a dedicated committee of people plan and then execute on the Harpswell Annual Hiking Challenge. And every year, the committee works its way through the planning process to bring to life another successful community-based recreational activity for Harpswell residents and visitors alike.

This year, the Hiking Challenge Committee included Gina Caldwell, Recreation Director, Town of Harpswell (The Town), Tom Carr, Chair of the Recreation Committee, Town of Harpswell, and Julia McLeod, Executive Director, Harpswell Heritage Land Trust (HHLT), among others who met 4 months in advance of the challenge to pre-plan. However, it was not always a joint venture between the two organizations. Early on it was just the Town who sponsored the challenge. But the Town is always looking for ways to collaborate with community organizations like HHLT and it eventually expanded to include some of HHLT’s trails.

The committee’s directive is complex. There are many factors that go into the planning of the hiking challenge. For example, choosing a date to avoid competing with other local activities is key, but Maine’s unpredictable weather will always remain a variable in the planning process. A tremendous amount of thought goes into choosing trail routes. Careful route design, accessibility, trail conditions and the proper signage keeps hikers safe and on the official route, especially at unmanned checkpoints. Time limits are equally important—they help hikers keep pace with the challenge requirements and give staff parameters when manning specific checkpoints. Safety is always the number one concern, and the committee considers foreseeable risks and identifies steps to ensure that the hikers avoid them.

The challenges of a challenge. This year’s challenge turned out to be a bit of a challenge. The committee made a few changes like modifying the trails to accommodate those who wanted to participate (i.e., parents with children) but not have to walk so far and stamps were used instead of stickers to earmark route destinations. Unfortunately, the numbers of participants were down in 2024. There could be several reasons for this according to Gina Caldwell. Firstly, it was a stunningly beautiful day in Harpswell. A great day for a hike and just about anything else you could think of doing outside. Secondly, this year garnered less volunteer support and public advertising than in the past. These two factors could have contributed to the lower number of participants. Nevertheless, hikers still came from as far away as Bedford, NH, Boston, MA, Richmond, VA, and Milo, ME.

Comments from the trails. When asked why they were doing it, many of the hikers commented on wanting to walk in nature, to take in the beauty of Harpswell, and to appreciate the generosity of those who donate their land to the Town or HHLT. One mother, daughter, father team commented that they completed the challenge every year but this year there was a trail on the program that they didn’t even know about. When Tim McCreight, HHLT vice president showed up at the sign-in station at the Town Hall, he was met by Tami McNelly who just arrived to pick up her t-shirt having completed all eight trails. Amazingly, Tami had walked four trails before going to work at the Bailey Island post office and then finished the other four by mid-morning. Tim also met and walked alongside Sandy Vance, a New Hampshire resident and her sister who recently purchased a home in Harpswell. Tim met Sandy at the trailhead of the Devil’s Back West and learned that she saw the challenge as a chance to get to know the town better and was only intending to hike one trail. However, when she finished one, she decided she might as well try another one. Fortunately or unfortunately, this is the effect of the challenge – you can’t just do one trail.

A race to the finish line. Organizing a hiking challenge is a comprehensive undertaking. It requires thorough planning, including consideration of trail routes and safety, effective community advertising and securing participant engagement. Year after year, the committee organizers carefully and thoughtfully address new and different challenges. And this meticulous planning creates memorable and enjoyable hiking challenges that celebrate the best of Harpswell’s beauty.