Letterbox Planted:    August 28, 2002

Length:                       Baldwin Drive; 5.7  miles

                                      Regicide Drive; 1.2 miles

                                      Lake Wintergreen Loop; 1.5 miles

Difficulty:                   Difficult for biking. Old pavement, with steep terrain. Not recommended for kids on bikes.

                                      Moderate for hiking. Paved, but steep climb.


Take exit 60 off of Route 15 (Wilbur Cross Parkway) and travel south on Route 10. Note that after 2 miles, Route 10 takes a right turn off the main drag and then takes a left turn. Easy to miss. Just past the large Beaverdale Cemetery on your right and across from Southern Connecticut State University, take a right onto Wintergreen Ave. If you look to your left you will see the South Overlook ridge. After 0.7 miles you will see signs for the State Park. Take the left over the bridge and then a right at the stop sign. Take a left at the next stop sign onto Brookside Rd.  You will pass by the Park entrance (Regicide Drive) on your left (if closed proceed to the West Rock Nature Center, just before the bridge under Route 15 and park in their lot). If you continue along Wintergreen Ave you'll pass by Main St on your left. Just down Main St is the Lake Wintergreen parking lot

There are three different areas in the park that are worth exploring either by biking or hiking. From the Park entrance you have two routes available to you. The southern route follows Regicide Drive up to the South Overlook and Judges Cave, while the northern route takes you up the abandoned Baldwin Drive and along the ridge line. This route leads to my Letterbox. There is also a trail that encircles Lake Wintergreen. My directions allow you to visit all three areas on an extended bike ride. Just skip ahead any area you wish to bypass. Also the blue dotted Regicides Trail extends 7 miles along the western edge of the ridge from the South Overlook to York Mountain where it ends at the Blue-Blazed Quinnipiac Trail. For more information visit;  WEST ROCK RIDGE SP  and WEST ROCK RIDGE SP TRAILS .

Starting from the Park Entrance parking lot; Here the road splits, with the right road heading north past the metal gate on Baldwin Drive and the left road heading south on Regicide Drive up to the South Overlook and Judges Cave. Baldwin Drive is closed to vehicles, while Regicide Drive is open to vehicles from Memorial Day weekend to the last Sunday in October, from 8 a.m. to 6 p.m.

Heading South on Regicide Drive; This road was constructed in the 1890s by the city of New Haven. You ascend up the paved road for 0.8 miles to a fork in the road. This is a steep climb with hairpin turns along the way, but it's a pretty consistent grade. he junction is clearly marked with a brown sign.

Note; Taking the right fork brings you up to Judges Cave after only  0.1 miles. Check out the stone walls lining the road. Judges Cave was a refuge for the Regicides Edward Whalley and William Goffe for a period of time in 1661 and 1664, as they were evading capture by agents of King Charles II, seeking to avenge the death of his father Charles I, who was condemned to death in 1649 by 59 English Judges or Regicides.

Taking the left fork will take you past two overlooks to the end of the road at the South Overlook after 1.2 miles. From here you have a view of New Haven, the Harbor and Long Island. To the far left, you can see the reclining figure of Sleeping Giant State Park. To the left of the harbor are the trap rock cliffs of East Rock Park. To your right you can see the Yale Bowl alongside the West River.  

Heading North on Baldwin Drive; You ascend up the old paved road, constructed in the 1930s as a Works Progress Administration project, which is still in pretty good shape, but has loose gravel in sections until the road straightens out after the final curve. This is a steep climb with several hairpin turns. You quickly cross over the entrance above the Wilbur Cross Parkway Tunnel. After your second hairpin turn, look to your left for a stone stairway with an iron railing descending down to the road. This is after 0.4 miles. Walk up the stairs to a stone octagonal building, built into the hillside. This building is an air shaft for the Wilbur Cross Tunnel below. This looks like some medieval tower with its iron gated windows and steel door. Follow the stone path around the right side of this building to the high side. With your back to the building, you'll see a rocky slope in front of you and a Cedar tree to your right. To the right of the Cedar tree is a large flat rock area. Head uphill to the top of this rock area where it turns to grass. You'll now spot a grove of Cedar trees. In the middle of this grove is an Oak tree with its top missing. Go to the backside of this tree where you will find a pile of rocks. Simply remove the top flat rock to reveal  the West Rock Ridge State Park Letterbox. Continuing on up the road, you'll come to a sharp right hand turn where the road briefly splits. Keep right, as there is a side road to the left that leads down to a cell tower. At the 1 mile mark there will be a turnout on your left. The Blue and Orange Trails lead to an overlook of Konolds Pond along the ridgeline. As you go along the top of the  ridge, the road has both up and down sections. After 2.3 miles there will be another turnout on your left. A path to the right leads you to a large boulder with an overlook of Lake Dawson behind an earthen dam. There is another large turnout around 3 miles, but not much of a view and glass covers the pavement. Avoid if biking. Another 0.5 miles takes you under the power lines and you'll shortly pass by a small stone building on your left. It is believed to have once housed equipment for the AT&T telegraph line that used to cross the ridge. If you look to your left through the trees you can make out Lake Watrous, also dammed. After 5.5 miles you start your final descent. 

Note; You may continue to the end, all downhill, after 0.3 miles, but if your going to retrace your route, it's not worth the effort. You also have the option of continuing past the end for an on road bike route back to the Park Entrance parking lot with one leg of your trip utilizing the Lake Wintergreen Loop. This has less uphill sections and is along residential streets.

To Continue On-Road; Go to the end of Baldwin Drive. Caution! As you near the end, a turn around will veer off to your right as the road veers left around a hairpin turn. Just around this curve the road is blocked by an earthen berm designed to keep out cars. Walk your bike over the berm and continue along West Shepard Avenue, which is also closed to traffic. The pavement is broken up. Midway down the hill is a gate at the junction with Rayzoe Terrace. Continue straight down this road to the first intersection. Turn right onto Hill St and then a right onto Dunbar Hill Rd. At Chauncey Rd take another right. At the end, turn left onto Main St (no sign), which is actually a residential street and follow to the Lake Wintergreen parking lot at the 10 mile mark. 

Note; To finish your trip on-road, simply follow Main St to Wintergreen Av and turn right. This will bring you back to the Park Entrance parking lot.

For a more scenic route [Lake Wintergreen Loop], head into the Lake Wintergreen parking lot where you'll see a map signboard. The White Trail takes you right around the lake, while the Red Trail takes you left around the lake, where they meet at the southern end. We took the unblazed trail straight ahead, crossing over a culvert, with the narrow part of the lake to our left. At the intersection, turn left and follow the gravel/hard packed White Trail along the lake. The trail is slightly hilly as the lake widens out. After less then a mile, you come to where the Red Trail crosses over to your right and back towards West Rock Ridge. The Red/White Trail to your left is not suitable for bikes. Continue straight where you pass a brick building and come to Wintergreen Ave. The Red Trail behind the building will take you back along the lake. From the lake parking lot, go straight onto Main St and at the top of the hill, take a right onto Wintergreen Ave and follow it through two sharp turns, and then underneath the Wilbur Cross Parkway back to the Park Entrance parking lot. This is roughly an 11.3 mile round trip. Can you feel it in your legs?





MAY 22, 2015