Difficulty: Moderate. The hike is about 4 miles total. Bog bridging and rocky sections of trail also add to the challenge. The final stretch to the summit is fairly steep.

How to get there: Oak Hill is located in the Hothole Valley parcel of the Great Pond Mountain Wildlands. Enter the parcel by the South Gate, which is located on Route 1, just south of the Route 1-Route 176 intersection in Orland. (Route 176 is also called Surry Road.)

Hikers can choose between parking areas (and hiking routes) to hike Oak Hill. The first parking area is right outside the South Gate; and the second parking area is beyond the gate about 2.6 miles at the Hothole Brook Trailhead. The second parking lot is only accessible when the gate is open to traffic, 8 a.m. to sundown on weekends, mid-June through October. From either parking area, it is about a 2-mile hike to the summit of Oak Hill.

Information: Oak Hill is one of the many hills within the 4,300-acre Great Pond Mountain Wildlands in East Orland, which the Great Pond Mountain Conservation Trust acquired on June 30, 2005. The property is managed for wildlife habitat and low-impact recreation, such as mountain biking, paddling, hiking, snowshoeing, skiing, horseback riding, fishing and hunting.

The Wildlands is split into two pieces: the 1,075-acre Dead River parcel and the 3,420-acre Hothole Valley parcel.

Oak Hill is located in the Hothole Valley parcel, east of Great Pond Mountain.  In addition to Oak Hill, the parcel contains at least portions of Flag Hill, Flying Moose Mountain, Hedgehog Hill, Condon Hill, Hothole Mountain, Bump Hill and Mead Mountain. The valley is bisected by Hothole Brook, which winds north through swamps and beaver habitat to the pristine Hothole Pond. For recreation, the parcel contains nearly 14 miles of gravel multi-use roads, as well as footpaths that lead to views from several of the hills and mountains.

To hike Oak Hill from the South Gate parking area, walk past the gate and up Valley Road for a short distance, then turn right onto Esker Path, which is marked with a large sign. Not far down the trail, you will find yourself in beaver habitat. Trees lining the trail have been felled by beavers, and a large section of forest beside the trail has been flooded by beaver activity.

The 1.2-mile Esker Path winds through hardwood forest (beech, maple and birch trees) and a small stand of tall evergreens. The trail is narrow but well marked. Keep an eye out for some interesting boulders scattered throughout the forest.

At a juncture with the Drumlin Path, continue straight on the Esker Path, which ends at the Hillside Trail. Turn right onto the Hillside Trail, which is much wider and open to the elements. The trail heads north and begins to climb Oak Hill. In about 0.5 mile, turn right onto onto the narrow Oak Hill Path, which climbs to the unmarked summit of Oak Hill (about 820 feet above sea level) in about 0.25 mile. You will know you are at the top of the hill when you reach a sign where Oak Hill Path meets East Ridge Path. Open areas on the hill provide great views of nearby hills and mountains, including Great Pond Mountain to the west.

For a 4-mile hiking trip, return to the parking lot by
the same route. If looking for a longer hike, you can continue on East Ridge Trail (1.1 miles), which leads northeast to Flag Hill via Flag Hill Road and Flag Hill Trail.

Another option for hiking Oak Hill is to start at the parking area at the Hothole Brook Trailhead. But for this option, the South Gate must be open. From here, the route to the summit of Oak Hill starts on Valley Road, then turns right onto Red Pine Path, right onto Flag Hill Road, right onto Hillside Trail and left onto Oak Hill Path. This route is also about 4 miles, out and back, according to the map at the South Gate kiosk.

Use of the Wildlands is free, though donations are welcome in the iron rangers located at the North Gate and South Gate. Year round, visitors can park at the South Gate, North Gate or Dead River Gate.

Dogs are allowed but must be on a leash at all times, and dogs are not allowed on Hothole Brook Trail or Great Meadow Trail to protect wildlife denning areas and corridors. Also, owners are responsible for picking up after their dogs.

Geocaching is allowed. To search for Wildland caches, visit www.geocaching.com. If you want to place a cache, contact the Great Pond Mountain Conservation Trust first.

Camping and fires are by permission only in two designated campsites for a small fee. Carry in, carry out. For information, visit www.greatpondtrust.org, call 469-7190 or email info@greatpondtrust.org.

Personal note: I tend to see wildlife in phases. I’ve talked about this before. For example, one summer, I saw upwards to 10 moose while hiking trails and driving along logging roads. Another summer, I couldn’t stop stumbling upon snakes. Then, there was the winter of woodpeckers. And now, I’m starting to suspect that I may be entering an autumn of porcupines.

I had never seen a porcupine in the wild until two weeks ago, when Oreo and I spied a porcupine climbing a birch tree in the new Hundred Acre Wood Trail in Brooklin. And now, we’ve met our second porcupine.

We were walking down Hillside Trail after an enjoyable hike to the top of Oak Hill when Oreo suddenly lunged forward. Just ahead of us, only a few feet from Oreo’s nose, a porcupine was wading through the tall grass lining the trail. The instant I saw his spiked body, I yanked Oreo in the opposite direction and wrapped his leash around a nearby tree for good measure. We waited until the porcupine had retreated a safe distance into the forest before continuing on our way, though I’m sure Oreo would have prefered to get better acquainted with the animal, to his detriment.

It was September 20, a warm and sunny fall day, and the usual green foliage was bleeding into orange, red and yellow overhead. After not being able to find much information online about Oak Hill, I was surprised to find that the hike provided several nice views of the Wildlands. Oreo and I stopped to take in a view near the end of the Esker Trail in a small clearing by a large tree and boulder (which was nice to sit on while taking a drink). And the views only got better as we climbed up the Hillside Trail and then Oak Hill Path. I’d suggest this hike (or snowshoe) to anyone looking for a beautiful, quiet, moderate hike in the wilderness. And if you’re quiet, you might even come across a beaver on the Esker Trail.

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...