Situated along the eastern edge of Dutchess County, Dover embodies the quintessential rural charm of New York’s Hudson Valley region. Named after Dover, England—the hometown of an early settler—this picturesque town was officially formed in 1807, though its history extends much further back in time.

The town’s indigenous heritage dates to 1637, when Pequot Sachem Sassacus purportedly took refuge in what is now known as the Dover Stone Church. This remarkable natural rock formation features a cathedral-like cave entrance with a flowing waterfall inside, creating one of the region’s most distinctive geological landmarks. The Stone Church has been drawing visitors for centuries and was designated to the National Register of Historic Places in 2014.

Dover’s landscape is defined by the Ten Mile River, which flows northward through the center of town before turning eastward into Connecticut to join the Housatonic River. The river is stocked with rainbow trout, providing excellent fishing opportunities, and when water levels are high, experienced kayakers navigate its whitewater sections. This watershed, along with the Great Swamp—New York’s third-largest freshwater wetland—forms a crucial ecological corridor through the eastern part of the town.

One of Dover’s most celebrated natural features is the Appalachian Trail, which traverses the town offering hiking opportunities across varied terrain. Along the trail stands the magnificent Dover Oak, “over 300 years old, with a 20′ circumference” and “reportedly the largest tree on the 2,180-mile footpath from Georgia to Maine”. This impressive white oak is registered on the New York State “Big Tree” Registry.

The town comprises several distinct communities, including Dover Plains, Wingdale, and South Dover, each with its own character and history. Wingdale, in the southern part of town, is home to Camp Ramah in the Berkshires on Lake Ellis, while Dover Plains serves as the central hamlet with historic buildings and convenient amenities.
Transportation connectivity is provided by two primary routes—NY Route 22 traverses north-south through the center of town, while Route 343 crosses east-west. The Metro-North Railroad’s Harlem Line includes stations at Dover Plains and Harlem Valley-Wingdale, offering direct service to New York City and making the area accessible for both commuters and weekend visitors.

Historic structures dot the landscape, including the J.H. Ketcham Hose Company, which has served as Dover’s fire department for over a century. The Tabor-Wing House, a well-preserved 19th-century home, offers insights into the architectural styles and domestic life of earlier eras.

Modern amenities blend seamlessly with Dover’s rural character. Local farms offer fresh produce, maple syrup production continues at operations like Soukup Farms, and unique experiences such as tours at Lucky Orphans Horse Rescue provide distinctive attractions for visitors. The Old Drover’s Inn, originally opened in 1750 as a tavern, now serves as a bed and breakfast with a restaurant, providing comfortable accommodations for those exploring the area.

With its combination of natural beauty, historic significance, outdoor recreation, and strategic location, Dover continues to attract those seeking an authentic Hudson Valley experience just two hours from New York City—a place where Revolutionary War history, geological wonders, and protected natural landscapes create a distinctive sense of place.