Letterbox Planted:    August 28, 2002

Last Updated:             January 27, 2024

Length:                       North Route; Baldwin Drive; 5.7  miles

                                      South Route; Park Entrance Road; 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 for 1.5 miles. Turn right on Woodin St to Wintergreen Ave.

To start from the Lake Wintergreen parking lot for the Lake Wintergreen Loop [Northern End]; Turn right, then take your first left on Main St. Parking lot will be on your left.

To start from the West Rock Ridge SP; Park Entrance parking lot [North & South Routes]; Turn left and follow the road underneath Route 15. Parking lot will be on your right. It's new in 2023, so I'm not sure if it's before or after the Park Entrance Road.

There are 3 Routes in West Rock Ridge SP that are worth exploring by bike: 

There is a Loop Trail that encircles Lake Wintergreen

From the West Rock Ridge SP; Park Entrance you have 2 Routes available to you. The South Route follows the Park Entrance Road South up to the South Overlook and Judges Cave, while the North Route takes you North up the abandoned Baldwin Drive and along the ridge line. 

I've created a Loop that allows to to bike both the Baldwin Drive; North Route & Lake Wintergreen Loop returning to the Park Entrance Road. 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; Travel up the Park Entrance Rd and quickly come to an Intersection

From this Intersection you have 2 Options:

Park Entrance Road; South Route: 

Option 1; Continue South up the Park Entrance Road (shared road). This road was constructed in the 1890s by the city of New Haven. You ascend up the paved road for 0.8 miles to an *Intersection. This is a steep climb with hairpin turns along the way, but it's a pretty consistent grade.

From the *Intersection; Right, North, 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.

From the *Intersection; Heading left, South, 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.  

Baldwin Drive; North Route: 

Option 2; Head right, North, past the gate along the old Baldwin Drive (closed to traffic). 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. You now travel 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 of Baldwin Drive, all downhill, to W Shepard Ave at 5.8 miles, but if your going to retrace your route, it's not worth the effort. You also have the option of continuing on-road from W Shepard Ave, South, back to the Wintergreen Ave 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 Southeast along West Shepard Ave, 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, South, onto Hill St and then a right, Southwest, onto Dunbar Hill Rd. At Chauncey Rd take another right, West. At the end, turn left, South, onto Main St (no sign), which is actually a residential street and follow to the Lake Wintergreen parking lot after 10 milesSee; Lake Wintergreen Loop Below.

Note; To finish your trip on-road, simply follow Main St East, to Wintergreen Ave and turn right, South. This will bring you back to the Park Entrance parking lot after an 11.5 mile Loop.

Lake Wintergreen Loop:

From the Lake Wintergreen parking lot [Northern End]; Map Board. The hard packed dirt & gravel White Trail travels straight, West, past the gate and over Wintergreen Brook. Come to an intersection at the Northern End of the lake and turn left, South, along the lake. The trail is slightly hilly as the lake widens out. After 0.8 miles, you come to an intersection at the Southern End of the lake with the Red & White Trail

Note; The Red & White Trail, which travels left, North, alongside the lake is not suitable for bikes. 

Continue straight, East and come to the Red Trail. Left, North, the Red Trail travels through the woods before crossing Wintergreen Brook to an open field next to the lake where it merges with the Red & White Trail before returning you to the Lake Wintergreen parking lot after a 1.5 mile Loop

Note; To return to the Park Entrance parking lot; If you continue right, South, it will bring you out to Wintergreen Ave. Travel right on-road and underneath the Wilbur Cross Parkway back to the Park Entrance parking lot





MAY 22, 2015