Sixteen Mile District

Ferncliff Forest is a 200-acre (0.81 km2) old-growth forest preserve of deciduous and hemlock trees located in Rhinebeck, a town in the northern part of Dutchess County, New York, USA. The property had been bought in 1900 by John Jacob Astor IV and remained in the Astor family until 1964, when it was donated as a forest preserve and game refuge.The preserve is maintained by a private nonprofit organization. Observation towers on the property were used for map-making, surveillance for President Franklin Delano Roosevelt's home during World War II, and recreational sight-seeing. Visitors can camp and hike the four miles (6.4 km) of trails free-of-charge. The most recently built observation tower in Ferncliff Forest measures 80 feet (24 m) tall, with 109 steps. It was erected in 2007, the first since 1941 in New York. In 1942, during World War II, the observation towers in Ferncliff Forest were manned by soldiers from the United States Army Air Forces 24 hours a day. The newest tower was constructed as a gift to the community for recreational purposes including hiking and mountain biking with an intricate trail system.

Mount Rutsen is a mountain in New York. It is located in the 200-acre (0.81 km2) Ferncliff Forest, west-northwest of Rhinebeck in Dutchess County. The Mount Rutsen (Ferncliff) Fire Tower is located at the summit.

Cox Farmhouse is a historic home located at Rhinebeck, Dutchess County, New York. It was built in the mid- to late-18th century and expanded and remodeled in 1843. It is a 1+1⁄2-story, L-shaped, stone-and-brick dwelling in the Greek Revival style. It is five bays wide and two bays deep and is topped by a gable roof. It features an elaborate, ornamented entrance.It was added to the National Register of Historic Places in 1987.

The Maples is a historic house located on 108 Montgomery Street in Rhinebeck, New York. It was built in the 1830s in the Greek Revival style. Three decades later, its exterior was remodeled, adding decoration in the picturesque mode. For decades, The Maples was used as medical offices. When the medical offices closed, the building was listed for sale, but remained empty for three years, falling into despair. In 2017, new owners purchased The Maples and began an extensive renovation, transforming the building into professional office suites. In 1987, it was listed on the National Register of Historic Places.

The Dutchess County Fairgrounds is the home of the annual Dutchess County Fair. Open for over 160 years, the fairgrounds are open year-round and host a number of events. Annual events include: Crafts at Rhinebeck [2] New York State Sheep and Wool Festival [3] Hudson Valley Wine and Food Festival [4] Rhinebeck Antiques Fair [5] Classic car showsIn addition to these events, the fairgrounds are home to "Turn of the Century Village" with a one-room school, a working sugar house, and a cider mill. There are plans to expand this exhibit. Dutchess County Fairgrounds is located on U.S. Route 9, about 3 miles from Amtrak's Rhinecliff-Kingston station.

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.

The Henry Delamater House is a historic house located at 44 Montgomery Street (US 9) in Rhinebeck, Dutchess County, New York.

The Beekman Arms Inn—formerly known as the Traphagen Tavern, Bogardus Tavern and Potter’s Tavern, and currently known as the Beekman Arms and Delamater Inn—is an historic inn located in the village of Rhinebeck, New York. It is within the Rhinebeck Village Historic District, a historic district added to the National Register of Historic Places in 1979 as a cohesive area of preserved historic buildings. In 2022 the Beekman Arms and Delamater Inn has also been a member of Historic Hotels of America, an official program of the National Trust for Historic Preservation, since 2006. The inn claims to be America's oldest continuously operated hotel.

The U.S. Post Office in Rhinebeck, New York serves the 12572 ZIP Code. It is located on Mill Street (US 9) just south of the intersection with NY 308 at the center of the village. It is a stone Colonial Revival structure built in 1940, during the New Deal. President Franklin Delano Roosevelt, a native of nearby Hyde Park, took a personal interest in its design, as he did with other post offices in Dutchess County built during his administration. He chose a ruined historic house, whose stones were used in the post office, as its model, and spoke at its dedication. In 1989 it was listed on the National Register of Historic Places. It is also a contributing property to the Rhinebeck Village Historic District.

The Rhinebeck Village Historic District is located along US 9 and NY 308 in Rhinebeck, New York, United States. It is an area of 167 acres (68 ha) contains 272 buildings in a variety of architectural styles dating from over 200 years of the settlement's history. It was recognized as a historic district and added to the National Register of Historic Places in 1979 as a cohesive area of preserved historic buildings.Its properties were developed primarily from the Colonial era to the end of the 19th century, when the district reached its present form. Three U.S. presidents have passed through here, most significantly, Franklin D. Roosevelt, who chose the design for a new post office during the 1930s, and spoke at its dedication. It is now one of the district's contributing properties. Today the area has become a popular local attraction, many of them housing boutiques and other small businesses. The streets are lined with large shade trees, bluestone sidewalks and other historic features.

Poets' Walk is located in Red Hook, New York, United States on the River Road (just north of the Kingston-Rhinecliff Bridge, New York State Route 199). It is intended to celebrate the connection between landscape and poetry. The classic wooden vistas, sunlit fields and thick forest were the main focus of landscape architect Hans Jacob Ehlers' vision for the property in 1849.

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.