The Winslow Trail, marked with red blazes, begins at the parking area at Winslow State Park. It climbs for 1.1 miles (1,100 vertical feet) through the forest and over bare granite ledge to the 2,937-foot summit of Mt. Kearsage.
The Winslow Trail climbs steadily out of the state park in its one mile ascent. You'll quickly cross underneath a power line that supplies the cell tower and fire tower with power on the summit. The forest is mixed with pine and some hardwoods. Take care with footing as there are a lot of roots and rock slabs on this climb. Around the 0.5 mile mark, the trail begins to climb much more sharply, and on a wet day, may even have some small streams coursing down it. Continuing up the trail provides occasional switchbacks and will break onto granite slabs offering some great views of the New London area with Pleasant Lake front and center. A stone's throw from the summit, the Barlow Trail
converges with the Winslow Trail, and together they climb to the top.
The summit has a fire tower that is occasionally open during the summer months and provides fantastic 360-degree views broken only by the cell tower that also occupies the summit. There is a small shelter on the summit with picnic tables in it for wind shelter should you want it during your summit lunch. Don't expect to be alone up here ever, as the climbs from the Rollins side are easy and suitable for small children as well.
Any offseason attempts on this trail need to factor the addition of the park road in. This road is one mile from the gate to the trailhead.