Dead River Picnic Path

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Dead River Picnic Path – 0.3 mi. Moderate; footpath. Veering left from the Dead River Trail about 0.6 mi. in from the gate, this path descends steeply through grassy meadows and young mixed woods to the east shore of Dead River. It ends at a peaceful wooded peninsula with a picnic table, and views up and down the Dead River.
Dead River Trail – 2.5 mi. Easy; gravel multi-use trail. This gravel multi-use trail traverses rolling terrain through young forests and meadows on the 875 acres between Great Pond Mountain and the Dead River, with occasional views to the west, especially as you rise higher up the mountain slope. Just before you come to the highest point on the Dead River Trail, a stone cairn and small trail signs point the way to a connector trail linking the Dead River Trail to the Stuart Gross Path and the trail to Great Pond Mtn. summit. A hike to Great Pond Mountain Summit via Dead River Trail is 3.5 miles one-way.
Drumlin Path – 0.4 mi. Moderate; footpath. Beginning at the first wide bend along the Valley Road, this path leads through mature softwoods to the first of four brook crossings, rising over three small drumlins (oval glacial gravel deposits) in between. You’ll find mossy rocks and diverse vegetation along the way: ferns, large ash and oak, hornbeam, witch hazel and hazelnut. The path rises through a mixed-hardwood hillside to emerge midway along the Esker Path. From South Gate, Esker Path to Drumlin Path and back along Valley Road makes a 2-mile loop.
East Ridge Path – 1.2 mi. Moderate; footpath. This path starts on Oak Hill West at the southwest overlook of Oak Hill Path, then works its way east along the bald summit ridge of Oak Hill, with views to the south, east, and northeast. As it descends the southeast side of Oak Hill, the path travels through a hardwood forest. Towards the end, there is a “jump” across Hemlock Brook, then the path emerges into a meadow and rises to join Flag Hill Trail.
Esker Path – 1.2 mi. Moderate; footpath of varied terrain. This rocky, wooded path starts 200 yards in from the South Gate on the right. It begins on an old woods road, crossing a wet area over a bogwalk. It then follows a small glacial esker (a raised glacial gravel deposit) for 0.3 mile with glimpses of Great Pond Mountain, passing over several small seasonal streams. As the path moves upland it crosses a wooded vale to several large boulders, and moves through a stand of hemlocks to a wide view looking west. It then works its way across the southern toe of Oak Hill, coming out on Hillside Trail.
Flag Hill Road/Trail/Path 1.9 mi. Easy to moderate; gravel multi-use trail to footpath. When the gate is open, cars can travel the first 0.7 miles on steep Flag Hill Road to the cedar barricade. From there you must walk, and the road becomes a multi-use trail for 0.4 mi. This grassy, gravel trail traverses a few gullies and the open corridor affords a nice view of the 1½-mile-long ridge of Oak Hill. Flag Hill Trail transitions into a rocky, steeper footpath leading 0.8 miles to the summit and a beautiful overlook of Branch Lake. On the way, this path offers glimpses of Rocky Pond, with panoramic views of coastal mountains from Acadia to the Camden Hills. Blazes and cairns lead to the summit of Flag Hill, crossing bare ledge with alpine vegetation, including blueberries.
Flying Moose Trail – 0.8 mi. Strenuous; gravel multi-use trail. This grassy trail takes you up a steep incline with a few level places and transitions to a footpath near the top, with a chance to pick blueberries. Though it can be a hard climb, the trail brings you to a beautiful western lookout over Hothole Valley to Great Pond Mountain.
Great Meadow Trail – 0.5 mi. Easy; gravel multi-use trail. As you travel this rolling trail, look to the left, about 0.2 mile in, high above the trail, to spot two large boulders. This trail comes to an end at a log landing and provides a good view of Great Pond Mtn.
Great Pond Mountain Trail

Via Stuart Gross Path – 1.1 mi. Moderate; footpath. Starting 0.9 mi. up Don Fish Rd. from the hatchery, the trail heads uphill through beech woods 0.4 mi then veers right to approach the intersection with the Dead River Trail Connector and the old Jeep trail up Great Pond Mountain. Go straight across the intersection onto Mountain Trail, and ascend on this wide bedrock trail. You'll soon come out of the woods to hike along a broad ridge; look for blueberries and the white flowers of rare smooth sandwort. Enjoy views to north and south before the last steep ascent through the woods to the bald summit. On top, bare ledges offer fine views including the Penobscot Narrows Bridge and bay. A short walk to the right, peer down on Hothole Valley and Craig Pond. To the left, look for snow-capped Mt. Katahdin on a clear spring day. Parts of this trail cross private property; stay on trail.

Great Pond Mountain Trail

Via Dead River Trail and Connector – 3.5 mi. Moderate, multi-use gravel trail to footpath. See Dead River Trail description. Just before you come to the highest point on the Dead River Trail, a stone cairn and small signs point the way to a connector trail linking the Dead River Trail to the Stuart Gross Path and the Great Pond Mountain Trail to the summit.

Hillside Trail – 2.1 mi. Strenuous to Moderate; gravel or rustic multi-use trail. Starting at Valley Road, the trail crosses the main headwater stream of Hothole Brook, then steeply ascends the east side of Oak Hill where a grassy, open gravel road transitions into a narrower, grassy trail. Along the way, there are wide views west to Great Pond Mountain overlooking Hothole Valley. The trail levels off after the Oak Hill Path intersection and crosses a few seasonal wet areas. The northern section travels through older hardwoods, encountering seasonal streams and large erratic boulders. Coming out of the forest, the trail turns northwest, crosses a stream and follows a grassy road over Cascade Brook, ending on Flag Hill Road.
Hothole Brook Trail – 0.8 mi. Moderate; gravel multi-use trail. On this rolling trail you cross a bridge over Hothole Brook, which will bring you to gorgeous views of Great Pond Mountain as well as views looking back to the east over Hothole Valley. The trail ends in a big clearing, after passing large, interesting boulders and red pines on the last section. At the clearing, peer to your left for a look at a large boulder field.
Hothole Pond Trail – 1.4 mi. Moderate; gravel multi-use trail to footpath. Rolling, grassy Hothole Pond Trail passes through a forest of young deciduous trees, encountering a small quarry, a meadow, and a beaver pond. As you near Hothole Pond, the trail becomes a wooded footpath; where the trail forks, the left spur leads to Hothole Brook, and the right spur to a flat boulder on the scenic pond’s shore.
Mead Mountain Trail – 0.7 mi. Easy to Moderate; gravel multi-use trail. On this gently rolling trail edged with raspberries, you will cross over Hopkins Meadow Brook and come to an end at a log landing.

Oak Hill Path – 0.4 mi. Moderate to Strenuous; narrow footpath. Beginning at an intersection at the high shoulder of Hillside Trail, Oak Hill Path rises through mixed hardwoods to the west summit of Oak Hill, with switchbacks ascending the steep hill. After climbing some stone steps, the path then emerges to a grassy, alpine meadow with grand views west to Great Pond and Mead Mountains and Hothole Valley, and looking north from Hothole Pond to Flying Moose Mountain. A second overlook faces Penobscot Bay, with the Penobscot Narrows Bridge and Craig Pond in the foreground. Oak Hill Path joins East Ridge Path at the second overlook.
Red Pine Path – 0.4 mi. Moderate; footpath. This path departs from Valley Road across from the outhouse near the central parking area, ascending a glacial gravel deposit. A side trail goes through a red pine plantation, then rejoins. The path passes near Cascade Brook, then over a seasonal brook before veering left across the hillside. The path turns right onto an old tote road which comes out on Flag Hill.

Compilation and description by H. Brown and P. Cote of GS Troop 372 in conjunction with the

GPMCT Paths Committee, July 2009

Trail Tips

Pick up a Wildlands trail map and guidelines at the Wildlands North Gate, Bald Mountain Rd.; or South Gate, Rte. 1 (just south of Rte. 176 jct.); or download one from
Trail mileages given are ONE-WAY.
Allow time to get to and from trailheads off the Valley Road. (Rule of Thumb: the average hiker walks approximately 20 minutes per mile).
Dogs are welcome but MUST be on leash.
Horses and bicycles are welcome on multi-use trails; foot traffic only on footpaths. Snowmobiles allowed on designated trails. See map at
Water, sunscreen, bug protection and adequate clothing and footwear are critical items to bring.
Please stay on marked trails (blue blazes) and leave plants and animals undisturbed!
If you enjoy our trails, please consider joining Great Pond Mountain Conservation Trust. Visit our website or send in form on map. Thanks!

Great Pond Mountain Wildlands

Trail Guide

Great Pond Mountain Wildlands, Orland

Great Pond Mountain Conservation Trust

PO Box 266, Orland, ME 04472

(207) 469-7190
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