Oakdale, New York

Oakdale is a railroad station on the Montauk Branch of the Long Island Rail Road, on the corner of Oakdale-Bohemia Road and Montauk Boulevard in view of Montauk Highway across Norman DeMott Park, in Oakdale, New York.

Dowling College was a private college on Long Island, New York. It was established in 1968 and had its main campus located in Oakdale, New York on the site of William K. Vanderbilt's mansion Idle Hour. Dowling also included a campus in Shirley, which contained the college's aviation program and athletic complexes, and small campuses in Melville and Manhattan. Dowling was composed of four schools: the School of Arts & Sciences, the School of Education, the Townsend School of Business, and the School of Aviation. Largely enrolling local Long Island students, the college offered a variety of bachelor's degree programs in the arts, sciences, and business, master's degree programs in education and business, and a doctorate in education.After years of financial difficulties, frequently changing leadership, declining enrollment, and a failed search to find an academic partner, Dowling's accreditation was revoked by the Middle States Commission on Higher Education and the college ceased operations on August 31, 2016.

Idle Hour is a former Vanderbilt estate that is located in Oakdale on Long Island in Suffolk County, New York. It was completed in 1901 for William Kissam Vanderbilt. Once part of Dowling College, the mansion is one of the largest houses in the United States.

The Oakdale Merge is a convergence of Sunrise Highway (New York State Route 27, NY 27) and Montauk Highway (NY 27A and County Route 85, CR 85) between the hamlets of Great River and Oakdale, in Suffolk County, New York, in front of Connetquot River State Park.

South Side Sportsmen's Club was a recreational club that catered to the wealthy businessmen of Long Island during the gold coast era from the 1870s through the 1960s. Its main clubhouse and other facilities were added to the National Register of Historic Places as the Southside Sportsmens Club District in 1973, and are today contained within the Connetquot River State Park Preserve.

Jacob Ockers House is a historic home located at Oakdale in Suffolk County, New York. It was built in 1880 and is a 2+1⁄2-story, four- by two-bay, frame dwelling with single story wings extending from the east and north elevations. It is sheathed in clapboard and rests on a brick foundation. It features a verandah with Doric order columns supporting the cornice.The house was owned by Jacob Ockers who organized the Bluepoint Oyster Company. It was added to the National Register of Historic Places in 1992.

The Connetquot River (also known as Great River) is a six-mile-long (10 km) river in Islip, New York. It is one of the four longest rivers on Long Island and is recognized by the state as a Wild, Scenic and Recreational River. It is particularly known for its brook, brown and rainbow trout fly fishing.

La Salle Military Academy was a Catholic school with middle school/junior high school and high school divisions located in Oakdale, New York. It closed in 2001, and the school's extensive campus is now owned by St. John's University, located in nearby Jamaica, Queens.

St. Johns Episcopal Church and Cemetery is a historic Episcopal church and cemetery on Montauk Highway on the northeast side, about 300' northwest of the junction with Locust Avenue, Town of Islip in Oakdale, Suffolk County, New York. The church is a small, rectangular one story building with a gable roof, wood shingle siding, and a simple painted wood exterior trim. It features a three-story, square, engaged tower with a shallow pyramidal roof. It was enlarged and remodeled about 1843 and restored in 1962; the stained glass window was added in 1873. The cemetery contains about 100 graves with burials dating from the late 18th century to early 20th century.It was added to the National Register of Historic Places in 1994.

Bayard Cutting Arboretum State Park is a 691-acre (2.80 km2) state park located in the hamlet of Great River, New York, on Long Island. The park includes an arboretum designed by Frederick Law Olmsted for William Bayard Cutting in 1886, as well as a mansion designed by Charles C. Haight. Today Bayard Cutting Arboretum State Park is one of the last remaining estates on the South Shore of Long Island. It has been listed on the National Register of Historic Places since 1973 as a historic district. Robert Fulton Cutting, known as the “first citizen of New York” and his wife Helen Suydam Cutting, niece to Caroline Astor, would frequent the manor house and estate as both William and Robert were brothers. Together Robert and William brought the sugar beet industry to the United States.

Westbrook, a large rambling house of many gables and tall chimneys on the South Shore of Long Island, lies on the west bank of the Connetquot River. The estate has been listed on the National Register of Historic Places since 1973 as a national historic district.

Indian Neck Hall was a country residence of Frederick Gilbert Bourne, president of the Singer Sewing Machine Company. Located on the Great South Bay in Oakdale, New York, it was reputed to have been the largest estate on Long Island when it was built in 1897. The Georgian-style home was designed by a noted architect, Ernest Flagg. In 1926, the property was sold and became La Salle Military Academy. St. John's University acquired the property in 2001 and offers a number of its graduate degree programs from the Oakdale campus.