The Lewisboro Town Park, located off of Route 35 in South Salem, NY has several trails and features of its own to make it worth exploring. The bonus is the town trail system connects with the Deer Hollow trail on the Ward Pound Ridge Reservation and makes for several nice training runs that can easily incorporate trails from the Leatherman’s Loop.
First, get to the park. It is about a mile east of the Cross River/Route 35/ Route 121 stoplight on the right side. If you are coming from the east (Ridgefield CT), you will pass a Mobil station on your right and the park is the next left after that. Look for a small white sign marked “Lewisboro Town Park.” The Town Park is listed in the “Walking Wild Lewisboro” booklet that is available for $5 at various Cross River and South Salem establishments.
In the park, bear to the right and follow the dirt road up the hill above the Little League field. You should park in the upper parking lot. The trails go up the hill from the parking lot – the trailhead is easy to find.
The town park trails and the Pound Ridge Reservation trails connecting to the Loop course are marked in blue near the top of the map to the left. The Loop course is marked in green and runs counterclockwise.
Early on, the trail splits into two trails but then rejoins further up the hill as a single trail again. Why two trails splitting and rejoining you may ask. I didn’t understand either until I read about the old ski hill that operated at the park until the early 1980’s. The trails were originally two ski trails, served by a rope tow! The tow rope and engine hut are still there at the top of the lift area (marked on the map—click the map to see larger version).
Moving on… the trail continues up the hill. Follow the trail as it turns left near the top of the hill. Take the first right turn on the trail. You will go under some power lines. This marks the boundary between the Lewisboro Town Park and the Pound Ridge Reservation. Once you follow the trail back into the woods (south) past the wires, you will see a Pound Ridge Reservation trailhead sign with information (and a sign in book!).
The total length in the Lewisboro Town Park is about 1/3 mile before you reach the Pound Ridge boundary. It is about a 250 ft vertical climb so it will get you warmed right up!
When you enter the reservation, you are on the Deer Hollow loop. The trail goes east (left) and west (right). Turning left will take you to the quarry climb (sand hill) known as “The Wall” on the Loop map. This is about a mile or so down the trail. If you go right, you will head towards the intersection of Deer Hollow and the pine trees trail.
You can construct several training loops by mixing the eastern and western half of the loop trails along with some middle and side trails (mainly the Brown trail) that the loop does not use.
For this article, I will describe a 4 mile “Eastern Loop” that skips the stream crossings (don’t worry, the next article will have both!).
At the Town Park Trail / Deer Hollow intersection, turn left (east) towards “The Wall.” At the first intersection, turn a sharp right onto the connecting trail. Take that a short distance (maybe 1/10 mile) and make your first left onto the Brown trail. Follow the Brown trail for about a mile, up and down two hills. At the bottom of the second hill the trail intersects with the Deer Hollow trail.
This section is part of the Loop course marked in green on the map above. Make a left onto Deer Hollow and follow it by the Kimberly Bridge and near the river to your right. This section is a bit more than 1 mile. The trail breaks out onto Boutonville Road (closed to vehicles) and crosses a bridge over the Waccabuc River just before Route 124. The mud flats begin just before Route 124 on an unblazed trail—make a left turn onto the trail from the closed roadway. The mud starts out right away and continues in the lower part of the flats.
The flats section are almost exactly 1 km long and end at “the Wall” after crossing back over the Waccabuc River (via a foot bridge). The Wall is an old quarry from the late 19th – early 20th century. The sandy quarry hill climbs about 100 vertical feet and a steep angle. Keep those legs pumping up the hill!
At the top of the Wall, the unblazed trail joins back up with the Deer Hollow trail and heads north (make a right). Another 1km run brings you to the next intersection where you turn right. You should recognize this intersection from earlier in your run. Take a right and head back up Deer Hollow westward. Your first right turn is the intersection with the Town Park trail. You will see the trailhead sign and the power lines. Make a right turn then a left and head back down the ski slope to the upper parking lot.
Let us know if you travel these trails and know of any features to watch out for. Next Town Park connecting trails article will describe the “Western Loop” that is about the same length (maybe a bit longer depending on which connecting trails you choose) and includes both the “Slashdown” and First Water crossing for a true Leatherman’s Loop feel.