Timothy Knapp House and Milton Cemetery

Bird Homestead, also known as the Bouton-Bird-Erikson Homestead, is a historic home and farm complex located in Rye, Westchester County, New York. It is owned by the city of Rye and was purchased in 2009. The property is situated on Blind Brook estuary, off the Long Island Sound. The property is adjacent to the Rye Meeting House. The main part of the house was built in 1835, and is a two-story, three-bay wide frame building in the Greek Revival style. It sits on a brick foundation and has a low-pitched, side gable roof. It features a one-story, full-width, front porch. Also on the property are a contributing two-story barn built in the 1880s and a long, one-story outbuilding.It was added to the National Register of Historic Places in 2010. It is operated along with the adjacent Rye Meeting House, by the not-for-profit Committee to Save the Bird Homestead.The home was owned by five generations of the Bouton-Bird-Erikson family for over 150 years. Henry Bird was renowned entomologist; his sons Roland and Junius were pioneers in the fields of paleontology and archaeology, respectively. Many of their discoveries can be seen at the American Museum of Natural History. Henry's daughter Alice Bird Erikson was an accomplished nature illustrator while Doris Bird spent more than forty years as the children's librarian at the Rye Free Reading Room.

Rye Town Park-Bathing Complex and Oakland Beach is a historic park and public beach located on Long Island Sound at Rye City, Westchester County, New York. It is located next to the separately listed Playland Amusement Park. It was designed in 1909 by architects Upjohn & Conable (Hobart Upjohn and George W. Conable) and landscape architects Brinley & Holbrook. There are six historically significant buildings and structures; they are the Mission Revival style Bathing Complex. This includes the Bathing Pavilion and two shelters, a restaurant (1910), the Spring House, and the Women's Bath House (1925).It was added to the National Register of Historic Places in 2003.

Rye High School is a public high school in Rye, New York. Rye High School is the only high school in the Rye City School District. It shares a building with Rye Middle School.

Rye Psychiatric Hospital Center was a 34-bed investor-owned mental health facility located in Rye, New York.

The Church of the Resurrection is a Roman Catholic church located in Rye, New York. The parish was founded in 1880, and the current church building was completed in 1931.

Rye Meeting House, also known as Milton Mission Chapel, Grace Chapel, and the Friends Meeting House, is a historic Quaker meeting house located at Rye, Westchester County, New York. The property is adjacent to the Bird Homestead. It is a one-story, wood-frame building on a stone foundation with two main volumes, a nave and an asymmetrical transept. The exterior is sheathed in clapboard and shingles and exhibits characteristics of the Stick style. The front facade features a 2+1⁄2-story bell tower. The building was built in the 1830s as a school house. It was moved to its present site in 1867, and enlarged in 1871, 1875, and 1877. At the time, the church was a mission church of nearby Christ's Church, an Episcopal church. The Quakers obtained the property in 1959. The property was deeded to the city of Rye in 2002.It was added to the National Register of Historic Places in 2011. In 2015, The Preservation League of New York State selected the historic restoration work completed on Rye Meeting House to receive an Excellence in Historic Preservation award.

Playland, often called Rye Playland and also known as Playland Amusement Park, is an amusement park located in Rye, New York, along the Long Island Sound. Built in 1928, the 280-acre (110 ha) park is owned by the Westchester County government. Beginning in 2018 the park has been operated under contract by Standard Amusements.

Airplane Coaster, known previously as the Aero-Coaster and the Aeroplane Dips, was a wooden roller coaster which operated at Playland Amusement Park in Rye, New York, from 1928 until 1957.

The Dragon Coaster is a wooden roller coaster at Playland amusement park in Rye, New York. Opened in 1929, it was designed and built by amusement ride creator Frederick Church, the co-inventor of the Racing Derby, another early 20th century amusement park ride. The Dragon Coaster has approximately 3,400 feet of track and is, at its highest, approximately 80 feet tall. There is a tunnel along its span, a common feature of wooden roller coasters from the 1920s, that resembles the body and open mouth of a dragon. It was featured in the film Fatal Attraction, Mariah Carey's music video "Fantasy", and Big, starring Tom Hanks. The Dragon Coaster is still in operation.

Christ's Church, Rye (formerly Grace Church), is an Episcopal church in the Diocese of New York, located next to the Boston Post Road (U.S. Route 1) in Rye in Westchester County, New York. Established in 1695, the parish is one of the oldest in the United States of America. Construction of the first church began in 1706; the present building, dating from the 1860s, is the fourth to be erected on the site.

The Rye Golf Club is a semi-private, municipally-owned country club in Rye, New York, and one of five constituent properties of the National Historic Landmark Boston Post Road Historic District. The centerpiece of the parcel is an 1854 Gothic Revival stone home known as Whitby Castle which was designed by American architect Alexander Jackson Davis. The club has an 18-hole golf course designed by Devereux Emmet and 2 swimming pools.

The Boston Post Road Historic District is a 286-acre (116 ha) National Historic Landmark District in Rye, New York, and is composed of five distinct and adjacent properties. Within this landmarked area are three architecturally significant, pre-Civil War mansions and their grounds; a 10,000-year-old Indigenous peoples site and viewshed; a private cemetery, and a nature preserve. It is one of only 11 National Historic Landmark Districts in New York State and the only National Historic Landmark District in Westchester County. It touches on the south side of the nation's oldest road, the Boston Post Road (US 1), which extends through Rye. A sandstone Westchester Turnpike marker "24", inspired by Benjamin Franklin's original mile marker system, is set into a wall that denotes the perimeter of three of the contributing properties. The district reaches to Milton Harbor of Long Island Sound. Two of the properties included in the National Park designation are anchored by Greek Revival buildings; the third property is dominated by a Gothic Revival structure that was designed by Alexander Jackson Davis. This district, which also has immense archaeological significance and importance to Native American, European-American and African-American heritage, was declared a National Historic Landmark in 1993. The three-quarters-mile (1.2 km) meadow and viewshed is one of fewer than a dozen such identified Indigenous peoples sites in all of New York State. In 2005, J. Winthrop Aldrich, former assistant to six successive Commissioners of New York State Department of Environmental Conservation (1974–1994) and Deputy Commissioner New York State Office of Parks, Recreation and Historic Preservation (1994-2003; 2007–2010), attested that the District was acknowledged to be "one of New York State's finest assets", "amply deserving the rare honor of National Historic Landmark designation by the Secretary of the Interior."