This is a well-marked trail hike passing over two of the "three summits" in the Case Mountain Recreation Area in Manchester - including Lookout Mountain with its views of Manchester and Hartford - and continuing along the Shenipsit Trail
to Glastonbury and Hebron. Blue/white blazes mark a spur from Shenipsit that brings you to a trailhead on Birch Mountain Road, across from another trailhead for access to Gay City State Park. Following this trail you can access all the trails at Gay City. This hike brings you straight through to the park entrance on Route 85.
Scouts BSA troops can use this to meet various hiking and nature requirements. This can also be used to satisfy the backpacking option within the requirements for the Camping merit badge, provided the backpacking trek is part of a campout. The trail brings your group directly past a youth camping area in Gay City State Park, which is available for reservation through the CT DEEP.
This hike is shown as one-way. Either arrange transportation ahead of time, or you can hike back the way you came.
The hike starts with the steepest portion, an ascent along the carriage path rising from the Spring Street trailhead. Hikers are shortly rewarded with the panoramic views at the summit of Lookout Mountain. On a clear day you can easily see all the way to Heublein Tower
in Simsbury, but even an overcast day allows for views of nearly all of Manchester.
From the summit, follow the yellow trail west, which will bring you to the blue-blazed Shenipsit Trail
along the top of a ridge. Turn right to follow the Shenipsit to the south. The trail will feature rocky terrain, a clear soil path through heavy ferns, mountain laurel groves, and additional views of Hartford for those paying attention.
The trail will descend before rising again, eventually higher than the Lookout Mountain summit. For much of this stretch the trail will remain free of the noise from the roads and suburban landscape nearby, and will feel much more remote than it is, until the blue/white spur to the left rises and descends again to Birch Mountain Road. (If you rather, you can continue on the Shenipsit to the clear-cut area with power lines, then turn left to head to Birch Mountain Road, then left again to reach the blue/white trailhead.)
Across Birch Mountain road you'll see a sign denoting the trail leading into the back of Gay City State Park. This trail descends further and eventually leads to a pond where wildlife can be spotted. Take care along the edge of the pond, as the trail is sometimes swampy or has slippery footing, with stepping stones that might be submerged. The trail eventually leads uphill, past the youth campsite and to the access road within the park. Bear right to head to the park entrance/exit. If you have the time and stamina, the other trails at Gay City can bring you past some ruins and some interesting rock formations.