Home - Steep Rock Trail Series


Just a little over an hour from the northern suburbs of NYC, in the northwest hills of Connecticut lies one of the best kept secrets in trail running around! If you are ready for a new challenge of some awesome trails, then the Steep Rock Trail Series brought to you by Steep Endurance is for you! In cooperation with the Steep Rock Association, the Steep Rock Trail Series gives runners a chance to experience the idyllic trails of the Steep Rock Preserves in Washington, CT. Each race offer its own sweeping viewpoints, lush forest single track trails and hillsides, babbling brooks and streams, old rail beds, rural landscapes, and of course the ever present New England fall foliage. With each subsequent race, runners will progress from a 10K up to a Half Marathon.

Macricostas Preserve

Hidden Valley Preserve

Steep Rock Preserve

History of Steep Rock Preserve

In the Spring of 1889, just as he was about to break ground on his own country house in Washington, Connecticut, the architect Ehrick Rossiter discovered that the wooded hillsides in his dramatic view to the west were slated for clear cutting. For him, there was only one thing to do. Using the construction money for the house, he bought the threatened land from the timber company and saved forever the 100 acres that now form the heart of the Steep Rock reservation. During his 36 years of ownership, Rossiter built carriage roads and small river crossings and invited his friends and fellow townspeople to enjoy the wild beauty of this section of the Shepaug River Valley. In 1925 Rossiter donated the land, which included the Steep Rock overlook, to a carefully chosen group of trustees, thus ensuring its preservation. Four years later the trustees purchased the area known as the Clam Shell, and in doing so preserved the view from Steep Rock. With little of the fanfare that sometimes surrounds such efforts today, these ten people quietly established a public land trust long before the idea of land protection became common. Since then, many landowners have given additional tracts to the Steep Rock Association, and today Steep Rock’s holdings include over 2,700 acres.

The 974-acre Steep Rock preserve offers hiking trails which follow the river banks and provide access into the hillsides above. Near its north end, there are vestiges of carriage roads, one of which leads from Tunnel Road to the site of the Holiday House (no longer standing), a hotel built in 1893 by philanthropist Edward I. Van Ingen as a retreat for young working women from New York City. The project took advantage of the Shepaug Railroad which, from 1872 to 1948, wound through the preservation alongside the river. One can still see the abutments of the small suspension bridge which enabled disembarking passengers to meet the Holiday House carriages waiting on the opposite bank. Farther downstream, trails traverse the slopes above the river and follow the double oxbows (where the river loops south, north, and then south again). Nearby is the railroad tunnel, a rough arch cut through the rock ledge which allowed just enough room for the locomotive and cars to pass through.

The section northeast of the Depot is known as Hidden Valley, a 650-acre tract characterized by densely wooded hillsides cascading into the meandering river below. This section also includes a rocky high point and small meadows, accessible by hiking trails. Hidden Valley was donated to the Steep Rock Association by the Van Sinderen family in 1963.

The level trail lying alongside the eastern bank of the river replaces the defunct railroad bed. It is easy to forget that passenger and freight trains rumbled through the entire length of the reservations from 1872 to 1948. Trails and woods roads remaining from the Van Sinderens’ equestrian and carriage-driving days criss-cross this tract of hardwoods, pine groves, and hemlocks, although many trails are not marked. A footbridge built across the Shepaug River in 1985 makes possible many pleasant loop walks. Care must be taken to avoid the goshawk area north and west of the footbridge in the nesting season. From April through June warning signs are posted and trails are then closed.

Purchased in 2000 in a “bargain sale” from Constantine Macricostas, the 238-acre parcel is also commonly known as “Meeker Swamp.” It was bought with a combination of funds from the Town of Washington, Connecticut’s Open Space and Watershed Land Acquisition Program, and the Steep Rock Association, via individual contributions. The unspoiled land – a mix of meadow, farmland, wooded ridge and wetlands — sits just north of Route 202, opposite the junction of Route 47, and makes a magnificent natural gateway to the town. Contiguous to four other previously donated parcels, as well as the pinnacle overlook above Lake Waramaug, the aggregate preserve now consists of 368 acres.

The central 238-acre parcel consists of 50 acres of prime farmland; 90 acres of woodland and rocky ridge, and 98 acres of critical wetlands, including the headwaters of Bee Brook, a major tributary of the Shepaug River. The site’s unusual geology represents the eastern limit of carbonate (marble) bedrock in this region of the state, and is where three bedrock units come together. Most significantly, the preserve contains one of the Town’s largest fresh water supplies within both bedrock and stratified drift aquifers.
Waramaug’s Rock, at an elevation of 1250' is a spectacular overlook providing panoramic views of Lake Waramaug and the surrounding countryside. Named after a chief of the Wyantenock Indian tribe, Lake Waramaug is the second largest natural lake in Connecticut, an ecologically vital habitat for wildlife and a recreational center for the Towns of Washington, Warren and Kent. The awe-inspiring views from the top are a rewarding dividend for the steep hike.

Steep Endurance

Steep Endurance is a newly formed company that organizes unique trail/ultra events in the Northeast. We aim to share our love of the trails and introduce the beauty of the singletrack to those who have yet to experience it. There is nothing like being on the trails under the canopy floating along on the technical terrain. We believe that the essentials to an awesome experience for the runner are a challenging course, like minded people to run with, and of course a great after party!