Several great trails with plenty of roots and rocks to keep things interesting. Some places are technical, but the majority is just plain fun. Several historical buildings along the route, and possibly even some wildlife.
How to get there:
From the Casco Bay Lines Ferry Terminal in Portland, take a ferry to Peaks Island. From there take a left onto New Island Ave. Then take a right on Brackett. When you begin heading down a long hill, look on your right for a sign that says "trail." This is the first and main trail that leads to the others.