The Harpswell Hiking Challenge is June 3-4! Hike the Cliff Trail for water views & fairy houses

The Harpswell Hiking Challenge is June 3-4! Hike the Cliff Trail for water views & fairy houses

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, roosty hike in between.)

It’s just one of Harpswell’s many waterfront trails (who knew!) and to celebrate those purty waterfront trails, the Harpswell Heritage Land Trust hosts the annual Harpswell Hiking Challenge, which is coming up on June 3-4. The challenge encourages hikers* to explore eight of Harpswell’s finest trails over the course of the weekend, and those who complete all eight hikes will be recognized as challenge finishers and get prizes (like water bottles and shirts and stuff). But really, the true prize is the pride you feel inside, right? (Eh, we still want the water bottle.) This year’s event culminates on Sunday with a “tailgate and recreate” event, complete with a horseshoe pit, corn hole, various other activities and a craft area, as well as food and music. (See the Facebook event for more info.)

* 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. Giant’s Stairs, for example, is an easy shore walk (dogs welcome!) and Houghton Graves Park boasts scenic views and picnic tables (picnics welcome!). See all eight trails on the list at

I visited the Cliff Trail in 2015 in honor of this 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 some 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:




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]

Harpswell Hiking Challenge

June 3-4, 2017. 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 Cliff Trail refreshment station or at the Town Office until June 10.

FMI: and


Shannon Bryan

Shannon Bryan

I don't like "exercise" any more than you do. But you know what I do like? Paddleboarding with a friend all afternoon (and then sitting in the grass to drink chardonnay). Bike rides and nachos, hikes, yoga classes held in breweries, group paddles to Fort Gorges, you get the idea. Because Maine is my gym.

1 Comment

  1. Thank you so much for posting our event! It’s growing each year and we are hoping to top the 130 hikers we had last year.

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