Raccoon Brook Hills Trail/Pine Meadow Lake/Diamond Mountain Loop

From the parking lot, head east (left when facing the woods), passing the Visitor Center to the left. You are following the red-on-white-blazed Pine Meadow Trail, which parallels Stony Brook, to the left. Continue ahead along this wide trail for 0.4 mile until you reach a fork. The yellow-blazed Stony Brook Trail, which proceeds straight ahead, will be your return route, but you should bear right and continue along the red-on-white-blazed Pine Meadow Trail.

The trail dips slightly to cross Quartz Brook. A footbridge over the stream has recently been constructed to the right, but when the water is low, the stream can easily be crossed on rocks. After crossing a gas pipeline right-of-way, the trail continues to follow a wide path along the hillside, high above Stony Brook (which can be heard below to the left).

About 1.2 miles from the start, the orange-blazed Hillburn-Torne-Sebago Trail joins briefly. Continue ahead on the red-on-white blazed Pine Meadow Trail. Soon, the blue-on-white-blazed Seven Hills Trail joins from the right. In another 500 feet, you’ll reach a junction. Here, the Pine Meadow and Seven Hills Trails turn left to cross Pine Meadow Brook on a footbridge, but you should continue ahead (don’t cross the footbridge), now following the white-blazed Kakiat Trail.

The Kakiat Trail climbs gradually for about a third of a mile until it reaches the start of the black-on-white-blazed Raccoon Brook Hills Trail. You’ll be following this trail in a short while, but for now, continue ahead on the white-blazed Kakiat Trail. The trail levels off and passes some huge boulders to the right. It then turns left to cross an intermittent stream and continues through a dense mountain laurel thicket, with an understory of blueberry bushes.

After climbing a narrow passage through rocks and passing jumbled boulders to the right, the Kakiat Trail is joined by the black-on-white-blazed Raccoon Brook Hills Trail. The two trails run together for about 100 feet, and when they diverge, turn left and follow the Raccoon Brook Hills Trail. The trail descends gradually for a short distance, then climbs steeply to an open rock ledge, with pitch pines and scrub oak. There is a view to the southwest from here, and it might seem like the summit – but it’s not. Just ahead, you’ll encounter another steep, rocky climb, with a wooden ladder placed at a particularly steep spot near the top.

At the top of the climb (elevation 1,150 feet), the trail comes out on a rock ledge with a panoramic southwest-facing view. This spot – the western summit of the mountain – is the halfway point of the hike, and it’s a good place to take a break. The trail continues along the crest of the ridge, soon once again coming out on open rocks, with more views. It then descends through thick mountain laurel, comes out on an open area, and climbs slightly to reach the eastern summit. Pine Meadow Lake is to the right, but the lake cannot be seen from the summit when there are leaves on the trees.

The Raccoon Brook Hills Trail now begins a steep descent. At the base of the descent, a junction is reached with the yellow-on-white-blazed Poached Egg Trail. Here, the Raccoon Brook Hills Trail turns left, but you should continue ahead on the Poached Egg Trail. This short trail proceeds through a rocky area to reach Pine Meadow Road West – an unmarked dirt road, built in the 1930s by the Civilian Conservation Corps (CCC).

Turn left onto Pine Meadow Road West, which runs near the shore of Pine Meadow Lake. In about a third of a mile, the road comes out on the lake shore. You’ll want to stop here and enjoy the beauty of this scenic lake. Built by the CCC in 1934, it was designed to serve children’s camps that would be developed around the lake, but these camps were never established.

Continue ahead and cross the dam of the lake (which was designed to accommodate a two-lane road). About 100 feet beyond the dam, turn left onto the red-on-white-blazed Pine Meadow Trail, which descends on a woods road. At the base of the descent, the Pine Meadow Trail curves sharply left, but you should bear right onto a footpath with blacked-out blazes. Follow this footpath uphill for about 200 feet to a junction with the yellow-blazed Diamond Mountain-Tower Trail.

Turn left on the yellow trail, which climbs Diamond Mountain on switchbacks. As you reach the top, there is an excellent view back over Pine Meadow Lake. At the crest of the ridge, the Diamond Mountain-Tower Trail ends at a junction with the blue-on-white-blazed Seven Hills Trail and the orange-blazed Hillburn-Torne-Sebago Trail. Turn left and follow the blue and orange trails, which soon reach a panoramic viewpoint to the west and north.
A short distance beyond, where the trails separate, bear right and follow the orange-blazed Hillburn-Torne-Sebago Trail. The trail descends very steeply for a short distance, then levels off and follows the ridge of Halfway Mountain for about half a mile. At a west-facing viewpoint, the trail begins a gradual descent to Pine Meadow Brook.

At the brook, the Hillburn-Torne-Sebago Trail bears left and crosses a footbridge, but you should turn right (don’t cross the footbridge) and follow the white-blazed Kakiat Trail, which proceeds over and around huge boulders. In another quarter of a mile, you’ll reach a junction with the yellow-blazed Stony Brook Trail. Turn left, now following both white and yellow blazes, and cross a footbridge over Pine Meadow Brook. A short distance beyond, the Kakiat Trail leaves to the right, crossing a footbridge over Stony Brook, but you should continue ahead on the yellow-blazed Stony Brook Trail. This section of the trail, which closely parallels the cascading brook, is particularly scenic.

After crossing a gas pipeline right-of-way and then Quartz Brook, the Stony Brook Trail ends at a junction with the red-on-white-blazed Pine Meadow Trail. Continue ahead on the Pine Meadow Trail, which parallels Stony Brook and leads back to the parking lot where the hike began.