Graham-Brush Log House

Stissing House is a restaurant in Pine Plains, currently characterized as a "country tavern". Clare de Boer owns and operates Stissing House. Previously, a French restaurant, also called Stissing House, operated in the space occupied by de Boer's restaurant.

The Pines is a historic home located at the hamlet of Pine Plains in the town of Pine Plains, Dutchess County, New York. It was built in 1878 and is a large 2-story frame residence with a 1+1⁄2-story service wing designed in the Stick-Eastlake style. It has an asymmetrical appearance with projecting bays, cross gables, and porches. It features a steeply pitched, common lap slate roof, four corbeled chimney stacks with terra cotta pots, and a tower with a steeply pitched pyramidal roof.It was added to the National Register of Historic Places in 1983.

Evergreen Cemetery, also known as Pine Plains Cemetery due to its location in that town, is an active cemetery located near the northern border of Dutchess County, New York with Columbia County, New York.

Pine Plains is a hamlet and census-designated place (CDP) in Dutchess County, New York, United States. The population was 1,142 at the 2020 census. It is part of the Poughkeepsie–Newburgh–Middletown, NY Metropolitan Statistical Area as well as the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area. The community of Pine Plains is in the town of Pine Plains.

Pine Plains is a town in Dutchess County, New York, United States. The population was 2,218 at the 2020 census.The name is derived from the geographic character of the region. The hamlet of Pine Plains is on the northern border of the county.

Thompson Pond in Pine Plains, New York is a 75-acre (30 ha) 15,000-year-old glacial kettle pond at the foot of 1,403-foot (428 m) Stissing Mountain. It is the source of Wappinger Creek, a tributary of the Hudson River that drains much of Dutchess County. The pond and mountain are part of a 507-acre (205 ha) nature preserve managed by The Nature Conservancy. The pond was designated a National Natural Landmark in May 1973 for its calcareous bog, unlike the more common acidic bogs in the Northeast.

Stissing Mountain, with an elevation of 1,403 feet (428 meters), lies in northern Dutchess County, New York, where it rises about 1,000 feet (305 meters) above its local footings. The mountain is steepest on its eastern slopes, which average 40 percent (or 21.8 degrees). This eastern escarpment is about 3 miles (4.8 km) long. Around Stissing's eastern base are substantial amounts of talus blocks composed of gneiss. A restored, 1933 fire tower is near the summit and open to the public (as of 2023) via hiking trails.

Silvernails is the site of a railroad junction between the former Poughkeepsie and Connecticut Railroad and Rhinebeck and Connecticut Railroad, in Columbia County, New York, United States. It is located in Gallatin, just outside Pine Plains; an old railroad station still stands at the site.

Silvernail Homestead is a historic home located at Ancram in Columbia County, New York and Pine Plains, Dutchess County, New York. It is an L-shaped building with a main block, with rear lean-to and ell. The main block is a 2+1⁄2-story, five-by-two-bay structure with a gable roof in the Greek Revival style. It features a single-story entrance porch with six restored Doric order piers. It has been occupied by five generations of the Silvernail family.It was listed on the National Register of Historic Places in 2010.

The Melius-Bentley House is a historic home located in the towns of Ancram, Columbia County and Pine Plains, Dutchess County, New York. It was placed on the National Register of Historic Places on August 11, 1982, and preserves several rare architectural features. The house is situated on a 24.8-acre (10.0 ha) parcel of wooded land on Mount Ross Road (County Route 50). The lot is divided by the Dutchess–Columbia County border.

St. John's Lutheran Church is a historic Lutheran church complex located at Ancram in Columbia County, New York. The complex includes the church, parsonage (ca. 1853), 19th century horse sheds, and church hall (ca. 1910). The church was built in 1847 and is a rectangular, heavy timber frame meeting house that received major modifications in 1854, 1886, and 1906. It is sparsely decorated in Greek Revival style. The current bell tower was added in 1886.It was listed on the National Register of Historic Places in 2009.

Pulver-Bird House is a historic home located at Stanford in Dutchess County, New York. It was built in 1839 and has a two-story center block with flanking one-story wings in the Greek Revival style. It features a monumental tetrastyle portico supported by four Doric order columns. Also on the property is a frame ice house and frame barn.It was added to the National Register of Historic Places in 2008.