A wooden bench sits at an overlook atop Oak Hill on Aug. 1, in Great Pond Mountain Wildlands in Orland.  Credit: Courtesy of Aislinn Sarnacki

The gravel road stretched before us, not a soul in sight. Tall white pines and slender birches rose to both sides. Fluffy white clouds scuttled across a rich blue sky. Every now and then they’d pass in front of the sun, shielding us from the heat of high summer.

As I followed the road with my dog, Juno, memories popped into my head of the last time I walked that same route in the Wildlands. It had been autumn, the trees displaying a riot of vibrant colors. And I’d been hiking with my former canine companion, Oreo. The thought was bittersweet.

Just a short drive from my home, the Great Pond Mountain Wildlands in Orland is an absolute treasure. The conserved chunk of wilderness covers 4,500 acres of hilly forestland, which visitors can explore on a vast network of trails and dirt roads that are closed to vehicles.

Juno walks up the grassy Hillside Tote Road on Aug. 1, in Great Pond Mountain Wildlands in Orland.  Credit: Courtesy of Aislinn Sarnacki

Since discovering the Wildlands several years ago, I’ve enjoyed walking my dog there, but always on leash. It’s the rules, plus there are a lot of porcupines in the Wildlands. And if you’ve ever experienced a dog-porcupine interaction, you’ll know why that should be avoided at all costs.

Owned and managed by the Great Pond Mountain Conservation Trust, the Wildlands is divided into two sections: the Dead River Parcel and the Hothole Valley Parcel. There are three major parking areas and a multitude of adventures you can pursue.

On that particular day in August, my goal was to hike to the top of Oak Hill, one of several small peaks on the property. Studying the detailed trail map (which is provided online and on a kiosk at the parking area), I decided on a loop hike that included the Esker Trail, Hillside Tote Road, Oak Hill Trail and Valley Road. It was just over 4 miles.

As I’ve found is the case with any hike, our trek to Oak Hill was filled with little surprises. Starting at the South Gate, we followed the smooth dirt surface of Valley Road to the Esker Trail, where we were greeted by a tree spirit. Just above my head, the wooden carving of an old man’s face was secured to a tree trunk. I don’t know its story, and I’m not sure I want to. I like the mystery and whimsy of it. I waved to him and continued on my way.

A carving is located on a tree beside the Esker Trail on Aug. 1, 2021, in Great Pond Mountain Wildlands in Orland.  Credit: Courtesy of Aislinn Sarnacki

The trail was narrow, leading us through a dense forest and across a long series of bog bridges. Just beyond a beaver bog I discovered a letterbox, a little wooden cubby that contained a logbook and rubber stamp. Using the written clues provided online, I’d found it easily. It also helps that I’d visited the letterbox before — four years prior.

Leafing through the logbook I found the entry I’d written, marked with my own personal letterboxing stamp that I’d crafted: a cartoonish spider. I hadn’t thought to bring the stamp with me to mark the logbook again, but I jotted down my name, the date and a short note.

Continuing on, we passed an intersection with the Drumlin Trail before running into a porcupine. The spiky creature was just ambling along the trail, but when it noticed us, it picked up the pace (as much as a waddling porcupine can, which isn’t much). Juno tugged on her leash, eager to inspect this fascinating and rather slow creature, which wisely approached the nearest tree and began to climb. Its claws scraped loudly against the bark as it slowly but steadily pulled itself out of harm’s way.

A porcupine climbs a tree beside the Esker Trail on Aug. 1, 2021, in Great Pond Mountain Wildlands in Orland.  Credit: Courtesy of Aislinn Sarnacki

At the end of Esker Trail, we turned right onto the grassy, wide Hillside Tote Road. Consulting the map, I was reassured that we were on the right path when we came to Domina Brook. There I sat on a rock and let Juno splash around in the clear, shallow water before starting a gradual climb to Oak Hill Trail.

At midday, the trees that lined the wide path provided little shade. The sun beat down, relentless. Damp with sweat, my shirt stuck to my back underneath my backpack. Half a mile later when we reached the start to Oak Hill Trail, I was eager to duck back into the cool shade of the forest.

Under the shelter of a leafy canopy, the narrow path wove uphill, over a few rock steps and plenty of twisted tree roots. Near the top of Oak Hill’s west peak, which rises 820 feet above sea level, two clearings provided open views looking to the west.

Great Pond Mountain dominated the view. Rising 1,030 feet above sea level, it’s the tallest peak and the most popular hiking destination in the Wildlands. Just south of it, the hump of Mead Mountain was visible — another great hike.

On the hike out, we followed Valley Road much of the way, passing a newly constructed mountain biking trail along the way. Just before reaching the parking lot, we met an employee of the Great Pond Mountain Conservation Trust who asked if I’d like to fill out a survey about my time on the property. I was happy to help, so I grabbed the clipboard and answered a few questions while he played with Juno.

The only answer I struggled with was offering advice about what the land trust could improve upon. The Wildlands is such a wonderful place to exercise and enjoy nature, I couldn’t think of anything I’d want to see changed.

Watch more:

Aislinn Sarnacki

Aislinn Sarnacki is a Maine outdoors writer and the author of three Maine hiking guidebooks including “Family Friendly Hikes in Maine.” Find her on Twitter and Facebook @1minhikegirl. You can also...