At just under 8 miles in length, this great loop run is highlighted by Judges Cave, Lake Wintergreen, and the South Overlook. The trail climbs along the gently undulating terrain of the Regicides Trail (Blue Trail)
before looping back to the south on the Red Trail
past Lake Wintergreen. Be sure to save some energy for the last leg-burning climb back up to the parking lot!
There is a composting toilet by the Lake Wintergreen parking lot, which is the only restroom facility available in the park. There is no water available at the park.
Standing at 627 feet, West Rock Ridge is one of the more prominent ridgelines in the New Haven area. As such, a run in the park promises some slightly more challenging climbs and rewarding views. For this run, start at the southern trailhead which is easily accessible from New Haven.
The run starts on the Regicides Trail (Blue Trail)
. This is one of the most challenging trails in the park as it follows the ridgeline north. From the trailhead, the trail is rolling, but climbs steadily along the ridge, gaining about 200 ft. in elevation over the course of the next 3.5 miles. Judges Cave, a small cave, can be found about a half mile into the Regicides Trail
near the junction with the Green Trail
. Take a short side trip on the Green Trail
to explore the cave, a fun detour.
From the Regicides Trail (Blue Trail)
, turn east onto the Purple Trail
, an mile-long connector that descends quickly to the Red Trail
. Turn south along the Red Trail
and enjoy a pleasant run along a mostly wide and flat trail. The trail passes along the east shore of Wintergreen Lake, a scenic lake that you may want to visit separately for a canoe or kayak outing. There are still a few small hills to contend with along the Red Trail
, but nothing too steep or long—that is until the end!
At just over 7.5 miles, you'll come to the southern end of the Red Trail
and the most difficult climb of the loop, a steep ascent back to the trailhead. This climb winds up the edge of the bluff, gaining over 100 ft. in a little over half a mile. You'll end back at the parking area at the South Overlook where you should take some time to enjoy the views. From here you can see Sleeping Giant State Park, East Rock Park, downtown New Haven, Long Island Sound, and Long Island.
Pack a snack or lunch to enjoy at the covered picnic pavilion at the trailhead post-run.