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Harpswell Hiking Challenge

The 2020 Harpswell Hiking Challenge event is cancelled.

Celebrate American Hiking Society's National Trails Day with the Harpswell Hiking Challenge and walk/hike/run eight trails in two days!

Harpswell, Maine's peninsula and 30+ islands have over 200 miles of coastline with beautiful views of Casco Bay and even Mount Washington. This is the 10th year for our hiking challenge. Each year we pick eight trails to hike with total hiking mileage of ~10 miles. You can hike all the trails in one day or over the weekend. Most the trails touch the coastline. Some are long and some short. See if you can complete our Hiking Challenge!
HQ table at Harpswell Town Office will be staffed from 9-4 Saturday and 9-3 on Sunday. Water, snacks, restrooms and information.

Join Harpswell Heritage Land Trust as we celebrate the grand opening of our newest trail at Little Ponds Preserve. Land trust volunteers will be on site to introduce visitors to Little Ponds from 10 a.m. to 2 p.m. You are invited to walk the trail, enjoy snacks and ask questions about the preserve or about the land trust. This lovely, intimate preserve offers a quiet walk through the woods any time of day, any time of the year. The easy trail circles through woods coming alive with spring growth, and there is a short spur to the cattail marsh, which provides habitat for a variety of birds. Please join us, and enjoy this small Cundy’s Harbor-area jewel! For more information about Little Ponds Preserve, visit

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