What if the northern terminus of the Eastern Trail at Bug Light in South Portland allowed a trail user to continue north through Portland, Falmouth, Cumberland, Yarmouth and beyond?
The Casco Bay Trail Alliance is focused on just such a vision, and you can view their efforts at: cascobaytrail.org.
Let them know you care about building more long-distance trails north of Portland, join their mailing list, and see how you might lend a hand to make this vision happen sooner rather than later.