The Dover Plains Stone Church is a small geological feature about three quarters of a mile west of town. The trail to it starts just off Route 22 and is a fairly mild hike (although good hiking shoes are definitely a plus, as the trail can get slippery). The walk to the Church starts with a straight path, lined with young maple trees, and continues west along Stone Church Brook. The Church itself is nestled in a small, steep canyon carved out by the creek.

As you approach the entrance the reason for the Stone Church’s name becomes very clear. The Brook has carved out the stone into a triangular entryway resembling the shape of a steeple. Sunlight streams in through the fissure in the cave ceiling and dances on the water, filling the Church with a sublime, sparkling glow. A large monolith at the back is perfectly placed to earn its nickname “the pulpit.” The waterfall at the back of the cave is about 30 feet high, although only a small portion of it is visible from the cave front.

Local legend tells of the Church serving briefly as a hiding place for Pequot sachem Sassacus. The Pequot were a Native American tribe who inhabited much of present day Connecticut who came into armed conflict with a coalition of British and Mohegan in 1636. Following the Mystic Massacre and Pequot War, the few surviving Pequot fled with Sassacus, seeking safe haven in New York. While there’s no evidence that Sassacus actually took refuge in the Church, it’s not beyond the realm of possibility and the story is popular in the Dover community. Sassacus himself would make it further into New York but would ultimately be killed by Mohawk, his scalp sent back to Connecticut as a show of good faith to the British.

In the late 1800s to early 1900s, the Stone Church would become a popular tourist destination, especially after the construction of the New York Central Railroad’s Harlem Line came through Dover Plains. Recently the Dover Stone Church Preserve added 50 acres to their holdings around the Church, bringing the total to around 170 acres, developing hiking trails and overlook points.