Van Vredenburg Farm

The original section of the Grove (ca. 1795), the country seat of Philip Jeremiah Schuyler and, subsequently, Mary Morton Miller, embodies the prototypical two-story, five-bay, center-hall form associated with the Federal period. Schuyler was married to Sarah Rutsen, and the land had been in the Rutsen family. The Landsman Kill, running through the property, had been the site of the Rutsen family's grist and saw mills, important settlement period industrial concerns in Rhinebeck during the early- to mid-eighteenth century. Schuyler acquired the mills, which he continued to operate, and a large parcel of land upon which he erected his elegant Federal style mansion. (The subsequent evolution of the Grove, in form, scale and decorative detailing, and its nineteenth-century historical associations place its primary significance in a later period as a 19th-century country seat. A carriage house on the property was built in the 1890s and is attributed to the architectural firm of McKim, Mead & White.It was added to the National Register of Historic Places in 1987.

Salisbury Turnpike Bridge is a historic stone arch bridge located at Rhinebeck, Dutchess County, New York. It was built in 1858 and is a single span stone masonry structure built of mortared random fieldstone. Pilgrim's Progress Road Bridge is about 500 feet (150 m) southeast of this bridge.It was added to the National Register of Historic Places in 1987.

Pilgrim's Progress Road Bridge is a historic stone arch bridge located at Rhinebeck, Dutchess County, New York. It was built about 1858 and is a triple arch stone masonry structure built of mortared random fieldstone.The bridge is one of two stone bridges that carry Miller Road over Landsman Kill, the first, Salisbury Turnpike Bridge, is a single arch bridge east of New York State Route 308. Pilgrim's Progress bridge is found south of School House Lane, after Miller Road turns from east to south. It was added to the National Register of Historic Places in 1987.

The Neher–Elseffer House is located on U.S. Route 9 a short distance north of its intersection with New York State Route 9G in Rhinebeck, New York, United States. It is a frame house built in 1746, one of the rare pre-Revolutionary frame houses in the Rhinebeck area. Its current appearance reflects renovations made circa 1800, and the interior was altered in the 1830s. It is currently owned by the town and used for storage. In 2000 it was damaged in a fire, leading to some additional renovations and repairs. In 2003 it was listed on the National Register of Historic Places.

Sipperly-Lown Farmhouse is a historic home located at Rhinebeck, Dutchess County, New York. The farmhouse was built about 1868 and is a one and one half to two story frame cruciform plan building in a picturesque, Gothic style. It features a variety of late Victorian era, eclectic wood ornamentation. Also on the property are a contributing barn, Dutch barn built about 1800, machine shed, and a corn crib.It was added to the National Register of Historic Places in 1987.

The Robert Sands Estate was a historic home located at Rhinebeck, Dutchess County, New York. The house was built about 1796 and is a 2+1⁄2-story, brick filled wood-frame building, with a gable roof and sheathed in clapboard. It sat on an extant stone foundation and measured five bays wide by four deep. Also on the property were a contributing 1+1⁄2-story frame cottage and four frame farm outbuildings, including a Dutch barn.It was added to the National Register of Historic Places in 1987. In 2015 the National Park Service, which oversees the Register, announced that it was considering a request to remove it as a result of a 1999 fire that left only the foundation. It did so in August of that year.

Traver House is a historic home located at Rhinebeck, Dutchess County, New York. It was built about 1730 and enlarged about 1790. It is a one to two story, stone and frame building built into a hillside. It has a slate covered gable roof. Also on the property are a contributing well / well house and stone retaining wall.It was added to the National Register of Historic Places in 1987.

The Old Rhinebeck Aerodrome is a living museum in Red Hook, New York. It owns many examples of airworthy aircraft of the pioneer era, World War I and the Golden Age of Aviation between the World Wars, and multiple examples of roadworthy antique automobiles.

J. E. Traver Farm is a historic home and farm complex located at Rhinebeck, Dutchess County, New York. The late-Federal style farmhouse dates to the 1790s, with modifications in 1849 and additions in the late-19th and early 20th centuries. It is a two-story, frame, five bay center hall plan dwelling on a fieldstone foundation. It features late-19th century picturesque ornamentation and a one-story, hipped roof verandah. Also on the property are a two contributing barns and a wagon shed.It was added to the National Register of Historic Places in 1987.

The Jan Pier House is a historic home located at Rhinebeck, Dutchess County, New York. The farmhouse was built about 1761 and remodeled about 1881 in a Second Empire style. It is a one- to two story, asymmetrical stone building built into a hillside. It features a Mansard roof sheathed in polychrome slate. Also on the property are two contributing barns, a smoke house, wellhouse / well, and a cistern.It was added to the National Register of Historic Places in 1987.

St. Margaret's Home, also known as Mrs. Astor's Orphan Asylum, is a historic Episcopal orphanage located at 7260 South Broadway in Red Hook, Dutchess County, New York. It was built in 1852, and is a two-story, Italian Villa style brick building with brownstone trim. It features a front porch with fluted cast iron columns, French windows, and round arched center double entrance. Its construction and operation until 1872 was supported by Margaret Rebecca Armstrong Astor (1800-1872), wife of William Backhouse Astor, Sr. (1792-1875) From 1872 to 1875, its patron was Margaret Astor Ward Chanler, wife of John Winthrop Chanler (1826-1877), after which Congressman Chanler until his death in 1877 and afterwards the Chanler Estate. The orphanage closed in 1932.: 3, 10–11 It was added to the National Register of Historic Places in 2006.

The New York State Sheep and Wool Festival is an annual gathering of fiber-arts enthusiasts in the United States that draws approximately 30,000 visitors and more than 300 vendors. It is held at the Dutchess County Fairgrounds in Rhinebeck, New York.