Woods are good. Water views are wonderful. Toss in a fairy house village and you’ve got yourself a fine hiking adventure.

The Cliff Trail in Harpswell is a splendid 2.3-mile loop that runs along Strawberry Creek on one side and has stunning views of Long Reach from 150-foot cliffs on the other side. (With a scenic, rootsy hike in between.)

It’s just one of Harpswell’s many waterfront trails, and to celebrate those good-lookin’ waterfront trails, the Harpswell Heritage Land Trust hosts the annual Harpswell Hiking Challenge, which is June 1-2, 2019. The challenge encourages hikers* to explore eight of Harpswell’s finest trails over the course of the weekend, and the first 100 people to complete all eight trails win a t-shirt. But really, the true prize is the pride you feel inside, right? (Okay, we still want the shirt.)

* By hikers, they mean you, even if you’ve never been much of a “hiker.” You don’t have to summit Katahdin to appreciate Maine woods and trails. Mitchell Field , for example, has flat, paved and gravel trails (dogs welcome!), and Houghton Graves Park boasts scenic views and picnic tables (picnics welcome!). See all eight trails on the list at hhltmaine.org.

I’ve visited the Cliff Trail a few times since I learned about this annual challenge and, well, wow.

Gaze upon Strawberry Creek, which runs along side the first portion of the trail.
Gaze upon Strawberry Creek, which runs along side the first portion of the trail.

The Cliff Trail is relatively flat to start, but there are plenty of exposed roots that some of us clumsier walkers might stumble over. And that Strawberry Creek will steal your attention.

Things get a little bit steep.
Things get a little bit steep.

There is also steeper terrain (the better to get you up that 150-foot cliff) midway through the hike. It’s enough to get your heart pumping a bit, but then the woods always send my heart a pitter-patter.


There are signs alerting hikers to the upcoming overlooks (Overlook ahead! Don’t fall over! or something to that effect) but you won’t be able to miss those glimpses of Long Reach through the trees. I kept stopping to look, thinking this was the stunning view I’d come for. And then:




Cliff Trail maine
What a view! Judi celebrates atop the Cliff Trail in Harpswell. Shannon Bryan photo

Glorious, yes?

There’s an open space to sit on the rock, have a snack, and take it all in. Because views like this should be enjoyed in slow motion. And with snacks.

Eventually, though, you’ll have to head back home, but the trail has one more gem for you: The Fairy House Village.


Build a house or wander through the village to admire the homes already there. I’m pretty sure I captured a family of fairies in the photo above – they must’ve been returning home from a day of wish-granting.

Cliff Trail

The trailhead is at the far corner of the back parking lot at the Harpswell Town Office, 263 Mountain Road. [Map]
FMI: hhltmaine.org/conserved-land/public-access/cliff-trail/

Harpswell Hiking Challenge

June 1-2, 2019. To participate, print out the Hiking Challenge form, which has all the trail listed on it. Get hiking, and find the sticker box at each trail. Once you’ve gathered stickers at each trail, you can turn the form in during the weekend at the HQ table (where there will also be refreshments and snacks) at Cliff Trail. FMI: hhltmaine.org