Overview
This is a horse trail. The passive grade is borderline frustrating, achieving in two mighty switchbacks what could have been done without strain on a line straight up the gradient. Still, if you don't mind scooting along with no particular effort, this is not a bad trail, or shouldn't be. There are some pleasant views across the Trout Creek valley and on to Eightmile Mountain. There is plenty of room to camp at Trout Lake, where you will not be bothered. There are even historical indications that the lake once had cutthroat trout in it — if you could get to them past mats of water-weeds.
This trail is one of the most unstable in district history. Originally, it started at the Chatter Creek guard station, crossed Icicle Creek on the footbridge (now part of the Icicle Gorge Trail), and climbed up the east side of Trout Creek. After about a half mile it forked, with the new branch going across the slopes and over to Jack Creek. Then logging came, destroying both forks. So, the trailhead was moved. A new showpiece trailhead site was built up adjacent to the Rock Island Campground, near Jack Creek. 1.5 miles of new trail was built from there to connect to the older Jack Creek trail; and from that junction, a completely new 4.7 mile trail following Jack Ridge was built to Trout Lake. This is by far the most ambitious trail building project in the Leavenworth area since the CCC days.
With a really solid, scenic, easy trail and overkill facilities, you might think that this was a hotbed (hot saddle?) of activity. The fact is, there is basically little activity of any kind, and likely never was. It runs hot, and dry, soon after the snow is gone. The horses turn their heads up the Jack Creek trail to Meadow Creek, where the grass is greener and the shade is better. Actually, (unless something unexpected and unannounced has happened) horses couldn't reach Trout Lake right now if they wanted to. Logs blocking the trail on the steep slopes east of Jack Ridge put a decisive end to their forward progress; though annoying, hikers can crawl over or under without horrific effort. Which all boils down to one thing: you will have this trail all to yourself.
Details - Trout Lake
Trout Lake fork from Jack Creek Trail

Follow the Jack Creek Trail from the Jack Creek / Trout Lake trailhead. At 1.5 miles, after gaining a little over 600 feet elevation, find the unmistakable junction with the Trout Creek trail, doubling back sharply to the left.
The Trout Lake trail begins with several long switchbacks, partially broken with a few tiny ones. You gain 1000 feet in the next 2.2 miles — quite comfortable, and this is steep part! Round the north corner of Jack Ridge and things level out. Begin a long traverse along the east face. This is steep terrain, but hardly dangerous. The footing is quite good, and even if you stumbled off the downhill side of the trail, the brush would keep you from going far.
The logging checkerboard cuts

This seems distinctly odd, heading to a mountain lake on a level traverse. As you cut straight across steep slopes above the upper edge of a past clearcut, the historical checkerboard clearcuts can be seen clearly on the slopes on the other side of the valley. At 5.7 miles, drop a small amount of elevation to reach a camp and trail not far from Trout Creek. You can make connections to the rougher and unmaintained Windy Pass trail here.
View from Trout Lake trail

Old maps show the trail to Trout Lake crossing the creek to reconnect with the historical trail route. No longer so. The creek can be quite busy early in the season, and replacing a bridge here was not a desirable option. Instead, a dry-footed crew cut another 0.5 miles of trail on the west side in easy terrain. The trees are larger here; it starts to feel like wilderness. There is a gain of about 250 feet elevation, followed by a slight drop, and you reach another trail junction, this one for the Jack Ridge Trail. Pass the junction, and immediately swing left toward the lake, at a large camp site.
Well, it would have been a large camp site, except that big fallen trees criss-cross it. That makes it more like a checkerboard of small camps. This has its own charm in a way; pleasant little compartments, and no difficulty finding a friendly log to sit on. If staying the night, I suggest hopping through to be closer to the outlet creek.
I suppose the lake is OK, but to me, no more appealing than many other shallow ponds found all over the Alpine Lakes Wilderness. I was not inspired to swim through the brush and wade the mucky water to try to get a photo. However, with the mosquitoes cooperating, this is a good place to stop for lunch.
Details - Jack Ridge
On the map, the trail looks appallingly difficult, but that is really not so. Both the east and the west sides have grades under the RidgeRat 1000 foot-per-mile threshold of pain. However, there are other pains that can be a significant deterrent.
Trail sign at Jack Ridge fork

Go back a few yards from Trout Lake, and you can find the well-marked Jack Ridge trail heading up the slope to the west. The sign is unfortunately the last of the trail maintenance you will see. The trail grade takes on a distinctly uphill attitude, and you have a little brush to and a few minor downed trees to pass. However, conditions here cannot be called terrible. Switchbacks take you up roughly 1000 feet in 1.2 miles. There are some excellent high views to the east as you follow the top of the ridge for 0.3 miles to the north.
Trout Lake and view from Jack Ridge trail

The trail makes an acute left turn, and begins descending switchbacks. These keep going, dropping about 2200 feet in 2.3 miles. It seems easier than that, but going downhill can alter impressions. The forest is just thick enough that there isn't much to see along the way, but that shouldn't matter over this short stretch. The bad news, unfortunately, is that you will encounter a downed tree or tree cluster roughly every 100 yards or so the entire way down. Horses will not get through this for the sheer number of obstacles to be passed. Hikers can pass, but will be slowed.
The trail comes out at the Jack Creek Trail, close to the creek. Just to the left, find a comfortable but seldom used creek-side horse camp. From here, follow the Jack Creek trail gently downhill 3.5 miles to the trailhead — a big loop! Or you can swing left and visit Meadow Creek.
As high mountain trails go, this could be one of the most comfortable around, were the fallen trees not allowed to dominate. It would be an easy weekend project for a volunteer crew to clear, since most of the fallen trees are not much larger than hefty sticks. But maintenance is not going to happen, not in this district, not on this trail.