Tumbledown, Little Jackson and Big Jackson Mountains

Tumbledown Mountain (3,069 feet) in Tumbledown Public Land might be the most popular hike in Maine (and it is one of the most beautiful). On nice days expect to see crowds of people hanging around at the summit, which has an enchanting pool (or rather tarn) surrounded by flattish ledges and backed by craggy peaks.

Tumbledown: To reach the tarn below the summit of Tumbledown, you have several good options: the 1.9-mile Brook Trail (elevation gain 2,080 ft), the 2.9-mile Parker Ridge Trail (elevation gain 2,180 ft.), the 2.0-mile Loop Trail (elevation gain 1,740 ft), and the 3.4-mile trek up the first part of Little Jackson trail over to Pond Link. The 3,069-foot western summit is 0.8 miles from the pond, along a beautiful open ridge.

In my opinion, the easiest way (but also the longest) up is to start up Little Jackson and then head over the Pond Link Trail. But there are no views along this route until you reach the tarn. However, if you head back down Parker Ridge Trail, you’ll get astonishing views near the summit.

The next easiest, and also quite a bit shorter, is the Brook Trail. The Loop Trail is very strenuous, basically hand over foot over the tumbled-down rocks up a steep pitch. Close to the ridge on the Loop Trail, at around the 1.3-mile mark, is what is called The Cave, where you have to squeeze through tightly-packed boulders. (The famous Fat Man’s Misery is a different rock formation to the right of the trail below the Cave.) The ridge between the western summit of Tumbledown and the tarn is gorgeous. Not to be missed.

Jackson and Little Jackson: The extensive trail network at Tumbledown includes trails to the summits of both Little Jackson (3,454 feet) and Big Jackson (3,555 feet). The hike up Little Jackson is harder and longer than to Tumbledown, and it is very exposed. The summit of Jackson Mountain is wooded, with no views, although the trail up offers a couple of open ledges with good views back over Little Jackson and beyond. You can also summit Jackson and Little Jackson from the north side of the mountain, via the Stockbridge Branch Trail.

Stockbridge Branch Trail (by Sam Shirley):
The Stockbridge Branch Trail offers a longer, more gradual, and much less busy approach to the Jacksons and Tumbledown. It also makes loop options possible in combination with a road walk on the Bryon/Weld Road. The trail follows an old snowmobile trail up a valley along the Stockbridge Branch of the Swift River, and it is occasionally marked with flagging tape and old diamond snowmobile trail markers.

Starting from the locked gate on the logging road off of the Weld Road, continue along the gated road for 0.8 mile. Just before a bridge over the river, the trail begins on the right. This turn is usually marked with flagging tape. The first stretch of the trail follows the route of an old woods road on the south side of the valley, high above the river. Other than a few washed out stream crossings, this stretch is easy going.

At 2.8 miles from the gate, the trail bears left off of the old roadbed towards the river. After a short section along the river, where the trail usually has water flowing on it, the trail begins to climb more steadily up the north slope of the mountain. The trail eventually reaches Jackson Pond and its small cabin at 4.3 miles from the gate. The tiny pond is one of only a handful of water bodies in Maine over 3,000 feet in elevation. It offers views of Jackson Mountain and Little Jackson Mountain. Past the pond, the trail crosses through a wet area before joining the Jackson Mountain Trail at 5.2 miles from the gate on the logging road.

Directions: From the intersection of Routes 156 and 142 in Weld, follow Route 142 north 2.3 miles and turn left onto Byron Road. Pretty quickly, the paved road changes to dirt. Continue approximately 4.3 miles to the Brook Trailhead on the right. Parking is on the left. Keep driving another 1.3 miles to reach the Loop Trail trailhead. You can park at the end of Morgan Road, off Byron Road, for easy access to Parker Ridge Trail and Little Jackson Mountain Trail. Byron Road is closed during the winter.