June 20, 2020 – South Salem, NY
Difficulty: Easy – moderate
Length: Approximately 4 miles
Max elevation: 764 ft. – total elevation gain: approximately 485 ft.
Route type: Circuit
Map: Leon Levy Preserve Trail Map
Trailhead parking: Smith Ridge Rd (NY-123) South Salem, NY 10590
The main entrance and parking lot is on Route 123 (Smith Ridge Road), just south of the intersection with Route 35. A white sign marks the entrance.
Preserve Overview:
The Leon Levy Preserve, formerly the Bell property, is 370 acres of forest and wetlands, located in the watersheds of both New York City and Stamford. About 90 acres lie within the watershed of New York City’s Croton Reservoir system, and the rest of the land drains into Stamford’s reservoirs. Leon Levy Preserve is owned by the Town of Lewisboro.

Leon Levy Preserve
The preserve is maintained by the Lewisboro Trail Volunteers, of the town Open Space and Preserves Advisory Committee. They work over 1,000 hours yearly, building, improving and maintaining the trails and features at Leon Levy Preserve.

Lewisboro Trail Volunteers
The preserve features wetlands rich in wildlife, a ravine with 75’ cliffs, diverse hardwood forest, rare plants such as Purple Milkweed and Blue Cohosh and a native plant garden adjacent to parking lot. The preserve has an extensive trail system, the ruins of the Black Mansion (1899-1979) and other outbuildings. In 2015, the Leon Levy Native Plant Garden was added by Lewisboro Land Trust.

Black Mansion ruins – Leon Levy Preserve
History:
Long before there was a Leon Levy Preserve, the area was home to bands of Algonkian-speaking Kitchawancs. Lake Kitchawan and streams provided a water source; Native Peoples were gone by the early 1700’s.
Part of the property, known in Revolutionary times as Keeler’s Ridge, was the encampment of Colonel Elisha Sheldon and his Second Continental Regiment of Light Dragoons.
- Circa 1790 – 1874 ~ First recorded property owner was Sgt. Jeremiah Keeler (1760 – 1835) who saw much action in the Revolutionary War. The property passed to his son Thaddeus at Jeremiah’s death in 1853.
- Circa 1890 – 1923 ~ Dr. James M. Crafts (1839 – 1917) purchased the property from the Keeler heirs and built the house on the hilltop between 1890 and 1900. He was called the first of the “City People” to build a summer home in South Salem.
- 1923 – 1959 ~ Abram I. Kaplan purchased the property from the Crafts heirs. The Kaplan family spent one season in the house and moved full time to another house on the property.
- 1959 ~ The property was purchased by the Bell/Lyden Partnership as an investment. No development followed.
- Circa Early 1960’s to 1979 ~ Mansion remained unoccupied and acquired the name “Black Mansion” by locals.
- January 28, 1979 ~ Black Mansion was destroyed by fire.
- 2005 ~ The property was purchased by Town of Lewisboro with contributions from the Jerome Levy Foundation, NYCDEP, and the Dextra Baldwin McGonagle Foundation.
Professor James Mason Crafts was an organic chemist and the fifth president of Massachusetts Institute of Technology from 1897 to 1900. Crafts was a professor of chemistry at Cornell College (1867-1870) and at MIT (1870-1880 and 1892-1897). He was one of the most highly regarded chemists of his era.

James Mason Crafts – image courtesy of Maureen Koehl
It was Dr. Crafts who built the mansion and many of the property’s enhancements. The Black Mansion, as it is known today, sat atop the hill, about 700 feet above sea level, one of the highest spots in Lewisboro, but so far up a winding drive that it was not easily seen from the highways.
In addition to the mansion, Professor Crafts built a coach house, a garage, an ice house and a laboratory. A cottage was built later for Mrs. Crafts’ daughter to spend weekends. The garage had six bays and a grease pit. The Keeler-era cow barn survived until about 2000, when it mysteriously burned as it was being restored.
In 1923, Mr. Crafts’ heirs sold the property to Mr. Abram Kaplan. The Kaplan family fortunes were tied to the sugar and molasses business in the Caribbean and to lumbering in New Mexico. Mrs. Kaplan did not like the house because the only heat in the mansion was generated from the fireplaces and she found it cold and drafty.
For whatever reason, the grand house on top of the hill was abandoned by the family and left derelict with all its furnishings and accessories in place. This made the empty house a target for vandals and adventure seekers out for a good time and a few souvenirs. Perhaps it was during this period that the house started being known as The Black Mansion. During the forties and fifties, it was called the Kaplan place.

Black Mansion – Leon Levy Preserve taken by Carol Gracie circa 1973
The Kaplans, in turn, sold the property to Robert Bell and his partner, Mr. Leyden. The acreage at the time reached from Route 35, all the way to Lake Kitchawan, and wandered along Ridgefield Avenue. Little by little parts were sold off, until it stood as it does today. Several attempts were made to develop the land, but none were successful. On a very cold winter night, January 28, 1979, at 12:35 a.m., the alarm bell rang at the South Salem fire house, the mansion is on fire! By the time the firemen arrived, the Black Mansion was “totally involved.” There was little to do but pump water on the blaze and try to contain the flames. The cause of the fire was never determined.

Black Mansion – January 28, 1979 – image courtesy of Maureen Koehl

Black Mansion Aerial – image courtesy of Maureen Koehl
In 2005, a partnership of public and private organizations succeeded in buying the former “Bell Property” and the Leon Levy Preserve came into existence. Lewisboro and Westchester Land Trusts worked with the Town of Lewisboro to negotiate the $8.3 million acquisition. The purchase was made possible because of a $5 million contribution from the Jerome Levy Foundation; $1 million each from the Town of Lewisboro and the New York City Department of Environmental Protection; and $500,000 over five years from the Dextra Baldwin McGonagle Foundation.
The land was named the Leon Levy Preserve in honor of the well-known Wall Street investor and founder of Oppenheimer Funds. The late Mr. Levy was the Jerome Levy Foundation’s primary benefactor. His widow, Shelby White, arranged the gift. “Our involvement in the project is a fitting tribute to Leon’s love for Lewisboro, and he would have been proud and pleased to see this land protected.”
An interesting side-note involving a member of the Kaplan family:
Joel David Kaplan, one of Abram’s sons, was arrested in Mexico in November 1961, at the age of 35. He was convicted in 1962 of killing a man, and sentenced to 28 years in Acatitla prison. After nine years in the Mexican prison, on August 19, 1971, a helicopter landed in the prison yard. The guards mistakenly thought this was an official visit. In two minutes, Kaplan and Kaplan’s cellmate Carlos Antonio Contreras Castro, a Venezuelan counterfeiter, boarded the craft and were piloted away. No shots were fired. Both men were flown to Texas and then different planes flew Kaplan to California and Castro to Guatemala.

Joel David Kaplan
The Mexican government never initiated extradition proceedings against Kaplan. The escape is recounted in a book, “The 10-Second Jailbreak: The Helicopter Escape of Joel David Kaplan.” It also inspired the 1975 action movie “Breakout” which starred Charles Bronson and Robert Duvall.

The 10-Second Jailbreak – image courtesy of Maureen Koehl
Trails Overview:
A combination of footpaths and carriage roads make up the approximately 5.5 miles of hiking trails that are within the preserve. They will be adding more trails over the next few years.
Some of the carriage roads on this former estate are wide enough to allow walking two or three abreast. Extensive stonework is apparent on the many at-grade raised roadbeds. The narrower footpaths require walking single file.
The trails are well marked as are the junctions, which are numbered and some have maps. The numbered trail junctions correspond with those on the trail map, making the trails easy to follow. The trail blazes consist of 2” x 6” pieces of colored aluminum of the appropriate trail color. Red blazes appear co-aligned with some of the marked carriage roads sporadically throughout the preserve, but there isn’t a Red Trail listed on the map. The red blazes are Lewisboro Horsemen’s Association permissible trails.

Silver Trail – Leon Levy Preserve
As of 2018, there are new trails on the east side of Route 123, directly across from the main entrance. Cross the road carefully, and ascend the steps on the other side to access these new trails.

Leon Levy Preserve
Hike Overview:
I visited the Leon Levy Preserve in May of 2016, when I first started this blog and enjoyed the experience. In keeping with the recent trend of hiking local, I decided to pay it a return visit. The preserve is well maintained, the trails are mostly all shaded and the landscape is quite scenic.
Due to Covid, the parking has been reduced to 14 cars and the preserve is only open to NYS residents.

Leon Levy Preserve
This hike is mostly a loop, with only retracing of steps on short sections of trails. It covers all of the main points of interest, including the Black Mansion ruins.

Leon Levy Preserve
The Hike:
The hike begins at the northwest end of the parking lot, to the left of the kiosk. The three blue blazes on the tree, mark the start of the Blue Trail (Main Trail). Follow the blue blazes as they head west into the preserve. In about 200 feet, the trail reaches Junction 1, where the Blue Trail turns right, which will be your return route. For now, turn left on the White Entrance Trail as it leads southwest on a woods road, gradually climbing the hillside. The White Entrance Trail curves to the north and in 0.3 mile, ends at Junction 19 (Blue Trail).

Trailhead – Leon Levy Preserve

start of Blue Trail – Trailhead – Leon Levy Preserve

Junction 1 – Leon Levy Preserve

Junction 1 – White Entrance Trail – Leon Levy Preserve

White Entrance Trail – Leon Levy Preserve

White Entrance Trail – Leon Levy Preserve

Junction 19 – White Entrance Trail – Leon Levy Preserve
Turn right on the Blue Trail as it heads northeast on another woods road. The Blue Trail is joined by another road that comes in from the left (not on trail map). Continue straight on the Blue Trail, soon passing Junction 23 (pink-blazed Cottage Trail). Stay on the Blue Trail and approximately 0.3 mile from where you began on the Blue Trail, it reaches Junction 3 (Yellow Trail). Turn left here, leaving the Blue Trail and now follow the yellow blazes up the hill.

Blue Trail – Leon Levy Preserve

Blue Trail – Leon Levy Preserve

Blue Trail – Leon Levy Preserve

Blue Trail – Leon Levy Preserve

turn left on Yellow Trail

Yellow Trail – Leon Levy Preserve
In about 210 feet, there is an unmarked woods road on the left with the Black Mansion ruins visible about 130 feet away. You may want to take some time to view this interesting structure.

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve
This 3-story fieldstone and shingle mansion was built as a luxurious summer home, the only heat was from large fireplaces. On the main floor were several large reception rooms, a grand entry, a paneled library and a music room with an Aeolian organ.

Black Mansion ruins – Leon Levy Preserve
This is the lone remaining column, of the pair that once adorned the front entrance.

Black Mansion ruins – Leon Levy Preserve
This brick enclosure may have been a root cellar. The roof, which was collapsing, was removed in recent years.

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve
The ceiling was decorated with blue sky and birds. To the rear was an elevator encircled by a staircase. On the second floor, a long hall led to the bedrooms and an art gallery. From the attic the view extended to Long Island Sound. The electricity was produced by acetylene gas.

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve
On the north end, there was a circular atrium or garden room/porch.

Black Mansion ruins – Leon Levy Preserve
When you are done examining the Black Mansion ruins, continue on the Yellow Trail near the north end of the ruins, passing Junction 4 (pink-blazed Cottage Trail). In just under 700 feet, the Yellow Trail reaches Junction 5 (Green Trail). Turn right here, leaving the Yellow Trail and turn right on the Green Trail. Follow the green blazes downhill as they head north then gradually curve to the south. When you reach Junction 9, continue straight (turning right leads to Ridgefield Ave.). The Green Trail winds its way through the woods as it descends into the valley, crossing through, then bordering a stone wall.

Yellow Trail – Leon Levy Preserve

turn right on Green Trail

Green Trail – Leon Levy Preserve

Green Trail – Leon Levy Preserve

Green Trail – Leon Levy Preserve
At the base of the descent, the Green Trail reaches Junction 7 (purple-blazed West Valley Trail). Turn right here, leaving the Green Trail and proceed ahead on the Purple Trail. The Purple Trail (West Valley Trail), travels through a remote and tranquil valley with wetlands, along the western edge of preserve.

Junction 7 – turn right on Purple Trail

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve
The Purple Trail crosses a small stream on a log bridge and a short distance later, reaches Junction 25 (White Stream Trail). Continue straight, still following the Purple Trail and crossing another small stream on a log bridge. The trail then borders a stone wall as it continues south.

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve
In about 0.3 mile, the Purple Trail turns left, climbs a little, then turns left again, crossing through a stone wall at Junction 9 (Yellow-Purple Trail). Stay to the right bordering the stone wall to remain on the Purple Trail, which turns right as it passes a high section of the stone wall.

Purple Trail – Leon Levy Preserve

Purple Trail – Leon Levy Preserve
The trail heads in a southerly direction and soon crosses through another stone wall. Next to the stone wall is the Shepherd’s Hut ruins.

Purple Trail – Leon Levy Preserve
According to Maureen Koehl, Lewisboro Town Historian: The “Shepherd’s Hut” is another fanciful name given by the trails’ head just for want of what else to call the ruin. I don’t think there was ever a bona fide herdsman on the land! It may have been some sort of animal enclosure when the property was more used for farmland during the Keeler ownership.

Shepherd’s Hut ruins – Leon Levy Preserve
Soon the Purple Trail veers southeast and ends at Junction 10 (Blue Trail). Turn left on the Blue Trail which heads northeast on a woods road. In about 140 yards, the Blue Trail reaches Junction 12 (Yellow Trail – South Gorge Rim Trail).

terminus of Purple Trail at Junction 10 – Leon Levy Preserve

Blue Trail – Leon Levy Preserve
The Yellow Trail (South Gorge Rim Trail) travels on a footpath along the edge of the cliffs, high above the gorge. The map shows that there is a view of the gorge (★), but perhaps only during leaf-off season. The trail curves around and ends at Junction 13 (Blue Trail). Turn right on the Blue Trail and follow it as it crosses over the gorge on a stone bridge.

Junction 12 – South Gorge Rim Trail

Yellow Trail – Leon Levy Preserve

Blue Trail – Leon Levy Preserve
The Blue Trail ascends a little and soon reaches Junction 14 (silver-blazed Gorge Overlook Trail). Turn right on the Silver Trail and follow it to the end. There is an interesting rock formation near the edge of cliffs that is worth seeing. Again, the map shows that there are two viewpoints from this trail, but only during leaf-off season. Follow the silver blazes as the trail loops around and returns to Junction 14 (Blue Trail).

Blue Trail – Leon Levy Preserve

Junction 14 – Leon Levy Preserve

Gorge Overlook Trail Loop – Leon Levy Preserve

Gorge Overlook Trail Loop – Leon Levy Preserve

Gorge Overlook Trail Loop – Leon Levy Preserve

Junction 14 – Leon Levy Preserve
Proceed northeast on the Blue Trail for about 0.4 mile, passing Junction 19 (White Trail) and then reaching Junction 23 (pink-blazed Cottage Trail).

Blue Trail – Leon Levy Preserve

Blue Trail – Leon Levy Preserve
Turn left on the Pink Trail and follow the footpath in a northerly direction, soon arriving at the Cottage ruins.

Junction 23 – Cottage Trail

Cottage Trail – Leon Levy Preserve

Cottage Trail – Leon Levy Preserve
The “cottage” appears to be a dwelling that at one time had a small patio on the NE side, probably built late 19th or early 20th century. We did find ‘modern’ heating and plumbing debris when we did an exploratory dig several years ago, but who lived there is another unknown. ~Maureen Koehl – Lewisboro Town Historian

Cottage ruins – Leon Levy Preserve
The Pink Trail continues around the southwest side of the ruins and soon ends at Junction 4 (Yellow Trail). Turn right on the Yellow Trail, passing the Black Mansion ruins and continue downhill on the road.

Cottage Trail – Leon Levy Preserve

Cottage Trail – Leon Levy Preserve

Junction 4 – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve

Black Mansion ruins – Leon Levy Preserve

Yellow Trail – Leon Levy Preserve
The Yellow Trail ends at Junction 3 (Blue Trail). Continue downhill, now following the blue blazes and turn right at Junction 2 (Blue Trail). Follow the blue blazes downhill and in a very short distance, the trail passes another set of ruins.

Continue straight past junction 3 onto Blue Trail

Turn right at junction 2, remaining on Blue Trail
The ruins with the tall chimney along the Blue Trail was a small house with an attached garage on the north side. It was surrounded by a flagstone walk/patio so we believe it was used as a dwelling at one time. During the ownership of Dr. Crafts, the builder of the mansion, the building was quite likely used as his chem lab in the early 1900’s. We did not find any lab detritus (debris) during several digs in this area, but found mid-century plumbing and heating artifacts and lots of burned and melted glass. This structure may have burned in the 1970’s as well. I have been told that it was rented during the 1950’s as a dwelling. ~Maureen Koehl – Lewisboro Town Historian

stone ruins on Blue Trail
Continue downhill on the Blue Trail turning left at Junction 1 and returning to the parking area, where the hike began.

Blue Trail – Leon Levy Preserve

Turn left at junction 1
Review:
This is a really good hike with a very interesting history. The combination of woods roads and footpaths compliment each other. The hike is almost entirely shaded, with the exception of the Black Mansion ruins, which is perfect for a hot and humid day. The scenic woods, stone walls, rock formations and ruins make this lovely preserve worth a visit. This hike was done on a Saturday morning and although there were several cars in the lot when we arrived at about 9:00 am, we only saw a couple of people on the trails during our visit. Extremely quiet and a very enjoyable day on the trails.
Pros:
Historical features, Black Mansion ruins, rock formations, well marked trails and junctions, lightly trafficked and well maintained preserve.
Cons:
None.
Take a hike!

Leon Levy Preserve
Sources:
- Special thanks to Maureen Koehl, Lewisboro Town Historian for sharing information and images.
- Leon Levy Preserve – Town of Lewisboro
- New York-New Jersey Trail Conference
- Lewisboro Land Trust
- An American and Venezuelan’s legendary Mexican helicopter prison escape