Day Trip CT: Historic Steep Rock Railroad Tunnel Provides Pathway to Foliage

I turned a corner and there it was gigantic and menacing, looming like a set piece from a Hollywood adventure flick—a circular hole in the side of a ridge surrounding a black vacuum of darkness.

I had driven 45 minutes, and thanks to faulty navigation, had walked more than three miles by the time we found the tunnel. It was bigger, by far, than I’d expected. Somehow overlooking the fact that trains had at one point passed through it, I’d envisioned something small and non-cave like. I couldn’t have been more wrong. Big enough to fit several buses through its opening, it looked like the type of place King Kong would be happy to call home.

Even as I got closer to the tunnel, no light emanated from the other side. I hesitated close to its entrance, peering unsuccessfully into its subterranean shadows. At first I thought it was my imagination, but as I got closer to the entrance I started to hear something echoing from within.(A view from within the tunnel. Below right: a  A spring view of the Tunnel from the north side, June 2, 1901.From the Collection of the Gunn Memorial Library and MuseumThis historic railroad tunnel is one of Connecticut’s coolest hidden attractions. It cuts a curving path through Steep Rock Ridge and can be found within the 974-arce Steep Rock preserve in Washington Depot. The 235-foot tunnel was made for the Shepaug Valley Railroad, which put the rural community of Washington Depot (then known as the Hollow) within a day’s ride of New York City. A crew of coal miners from Pennsylvania constructed it over nine months between 1871 and 1872. The crew often worked by hand using picks and also employed dynamite and nitroglycerin to blast through the ridge.The train operated until 1948 at which point the tracks were removed. Today, the area where the tracks once lay provides a flat, dirt pathway that allows modern visitors relatively easy access to the train tunnel.A trip to Steep Rock is a great sightseeing opportunity in any season but is particularly appealing this time of year when the fall foliage works its multicolored magic on the Connecticut countryside. From Steep Rock’s main parking lot (see directions below), the direct route to the tunnel is about 1.78 miles each way, along a mostly flat riverside trail. If you have time and energy for a detour you can brave some much steeper inclines and hike up to Steep Rock Summit, which with an elevation of 776 feet, provides a breathtaking view of the Clam Shell section (named for the land’s clam-like appearance) of the Shepaug River Valley.Ehrick Rossiter, a famous architect and graduate of The Gunnery, a private school in Washington Depot, donated the initial property for the preserve in the late 1800s. In the 1890s, Rossiter also designed a hotel called the Holiday House on the property for philanthropist Edward I. Van Ingen. The hotel was a retreat for working class women affiliated with Saint Bartholomew’s Church in New York City. The goal was to provide the women relief from the New York City sweatshops at which they toiled. The house no longer stands, but the old foundation can be viewed after a short walk from the parking lot.If you avoid other detours and walk directly to the train tunnel, you pass near the Hauser footbridge, a wood and cable suspension bridge over the river that shakes slightly as you walk on it and allows you to get a wonderful view from the center of the river as the colored leaves are reflected in the gently rushing waters below.As for the tunnel itself, as I hesitated outside of it, the echoes grew louder and closer. The source of these sounds turned out not to be some wild animal or mythical beast, as the irrational part of my mind had feared, but a friendly and harmless couple. After they good-naturedly admonished me for my hesitation at the tunnel's entrance, I went in. Within the tunnel it was cool and spectacular. Though it wasn’t fully dark, my cellphone flashlight did come in handy to examine the chiseled bedrock walls. As I navigated the small curve and approached the other side, the literal light at the end of the tunnel was a beautiful sight.

Bonus Trip: Hopkins Vineyard

If you have not gotten your foliage fill after a trip to Steep Rock, or are simply looking for some great wining and dining options, head to Hopkins Vineyard in New Preston.

About a 15-minute drive from Steep Rock, this vineyard is one of the most beautiful in Connecticut, and is located on rolling hills with panoramic views (below) overlooking Lake Waramaug. Given the spectacular vista, it’s little wonder the parking lot last week was filled with Ferraris and limos dropping off bridal parties for pre-wedding festivities. A tasting costs $8.50 and includes a sample of seven of the vineyard’s intriguing wines as well as a wine glass to take home. You can also buy a bottle and hold your own picnic outside, or buy full glasses and snack on fine cheeses at the vineyard’s wine bar.

Across the street Hopkins Inn offers breakfast, lunch and dinner with outdoor dining, and the same panoramic view overlooking the lake.Directions

To get to Steep Rock’s main parking lot use the address 2 Tunnel Road, Washington Depot. Be careful as some GPS navigation programs misidentify Steep Rock’s location, so make sure to type in the 2 Tunnel Road address.

Before embarking on the trail, it’s a good idea to print or bring an accessible copy of the trail map.

To the tunnel:

(Courtesy of Steep Rock Association)

From the main parking lot (next to the horse riding ring), take the yellow circle trail along Tunnel Road to the blue square trail to the Railroad Tunnel.

To steep rock summit:

(Courtesy of Steep Rock Association)

Park at the parking lot at the end of River Road and follow the green circle trail (aka old railroad bed) to the white diamond trail. Then take the yellow circle trail to the Steep Rock Summit.

(This article was originally published on a different platform. Some formatting changes may have occurred.)