Difficulty: Moderate. The hike is approximately 4.4 miles long, round trip, and gradually ascends to the top of Flag Hill, 925 feet above sea level.
How to get there: The South Gate to the Wildlands is located on Route 1, just south of the Route 1 and Route 176 intersection, in Orland. The gate is open to traffic 8 a.m. to sundown on weekends only, mid-June through October. Check the closing time at the kiosk.
For this hike, drive through the gate and continue for about 2.6 miles on the dirt road to a small parking area at the Hothole Brook Trailhead. Park, then cross the road to start the route to Flag Hill on Red Pine Path. If the parking area is full, park roadside.
(Looking at a map of the Wildlands, you will notice that there are several routes that will eventually lead visitors to the top of Flag Hill, but I am describing the shortest route, which can only be attempted when the South Gate is open to vehicles.)
Information: Flag Hill is one of the many landmarks of Great Pond Mountain Wildlands, two pieces of property that totals more than 2,300 acres in East Orland. The Great Pond Mountain Conservation Trust acquired the land in June 2005 and is working to purchase additional pieces land surrounding the two parcels.
The Dead River Section of the Wildlands is 1,075 wooded acres on the western and southern flanks of Great Pond Mountain, from the mountain’s summit to the shore of the Dead River.
Flag Hill lies in the other section of the Wildlands, Hothole Valley Parcel, which is 3,420 acres of wooded valley between the peaks of Great Pond Mountain (to the west); Oak Hill, Flag Hill and Flying Moose Mountain (to the east); and Hothole Mountain, Condon Hill and Hedgehog Hill (to the north). The valley is bisected by Hothole Brook, which flows north three miles through swamps and beaver habitat and feeds into Hothole Pond.
Approximately 14 miles of gravel roads traverse the Hothole Valley Parcel. Some are open to vehicle traffic mid-June through October on the weekends. All are open year round foot traffic, and many trails and roads are open to horses and bicycles. ATVs, dirt bikes and off-road vehicles are not allowed on the roads or trails, aside from snowmobiles, which are allowed on designated trails. Visitors may bring dogs on leashes on all roads and trails except for Hothole Brook Trail and Great Meadow Trail (due to an abundance of porcupines).
Hunting is also allowed in the Wildlands, but hunters must register by calling 467-7190 or by emailing email@example.com. The land has a hunting policy posted at greatpondtrust.org. Visitors should wear blaze orange during hunting seasons.
Located on the western edge of the Hothole Valley Parcel, Flag Hill rises 925 feet above sea level and its partially bald top offers views to the west of Branch Lake and Happytown Farm, a MOFGA-certified organic farm run by Paul and Karen Volckhausen.
The shortest route to the summit of Flag Hill starts at the small parking area at the trailhead of Hothole Brook Trail, which can only be accessed by vehicle from 8 a.m. to dusk on weekends, mid-June through October.
From the parking area, cross the road and start the hike on the Red Pine Path (which is 0.3 mile long). Red pines were planted in the area in May 1997, and the first part of the trail travels through a stand of these trees. The trail may be a bit soggy. A few bog bridges will help you travel over the messiest spots.
At the end of the Red Pine Path, turn right onto Flag Hill Road and hike about 0.5 mile. This road, which is also open bicyclists and horseback riders year round, and is open to road vehicles (no off-road vehicles) 8 a.m. to sundown on weekends from mid-June to October. During the summer, the dirt road is bordered by wildflowers.
At about 0.5 mile, Flag Hill Road leads to Flag Hill Trail (0.8 mile), which is closed to vehicles but open to bicyclists and horseback riders. A low wooden fence at the head of the trail bars the way for vehicles. Flag Hill Trail gradually narrows and is lined with a variety of wildflowers and raspberry bushes. It’s an excellent trail to observe birds and other wildlife. You will notice a gradual incline, especially near the end of the trail.
After hiking 0.8 mile on Flag Hill Trail (1.6 miles into the hike, total), you will start Flag Hill Path, which is 0.6 mile long and open to foot traffic only. The path is steeper and narrower than the trail, but it is marked with blue paint on the hill’s exposed bedrock.
There was no actual summit sign as of July 2013. You will notice that the trail actually travels past the summit and descends a bit before making a small loop. From the trailhead to the end of Flag Hill Path (a dead end), the hike is about 2.2 miles, making for a 4.4-mile hike, round trip.
For information about the Wildlands, including guidelines and maps, visit greatpondtrust.org. To ask specific questions about Wildlands, call 469-7190 or email firstname.lastname@example.org.
Personal note: Maine’s wild raspberries and blueberries were ripe on July 28, when I first hiked to the top of Flag Hill with hiking buddy Derek and my dog Oreo. Berry picking is one of the “welcome uses” of the Wildlands, according to the trust’s website, and we were glad for it. We stopped frequently to pluck a few of the delicious berries (of which there was an abundance), as well as point out birds (e.g. common yellowthroat, chickadees and red-eyed vireos) and insects (e.g. giant grasshoppers, beetles and butterflies). Summer was in full swing.
During the hike, we were passed by two mountain bikers (a man and woman), who locked their bikes to trees at the end of Flag Hill Trail and continued on foot to the summit of Flag Hill via Flag Hill Path. We caught up with them at the top, and as we were talking, another pair of hikers (a man and woman) reached the top of the hill. After a short chat, we went our separate ways to enjoy the views. A soft rain began as we descended the hill, and clouds crowded in front of the sun we’d enjoyed earlier in the day. Deer flies sped us up along the last legs of the journey. They emerged from God knows where and honed in on poor Oreo, ignoring the natural bug spray we lovingly spread through his fur earlier. When we got back to the car, he jumped in right away to escape their painful bites.