New Windsor Cantonment State Historic Site

National Purple Heart Hall of Honor is located along NY 300 in the Town of New Windsor, New York, United States, less than two miles south of the Town of Newburgh line and not far from the City of Newburgh. It is a Purple Heart national registry of military personnel that have been injured or killed during combat. In 1782, at his headquarters, George Washington created the Badge of Military Merit to be given to enlisted men and non-commissioned officers for meritorious action. The museum is located at the New Windsor Cantonment State Historic Site, the last encampment of the Continental Army.

The James "Squire" Patton House is located along the brief overlap of NY 207 and 300 in New Windsor, New York, United States. It is on a five-acre (2 ha) parcel owned by the nearby city of Newburgh, formerly used for police K-9 training. The house now sits abandoned and in a state of decay. It was built in 1790, although it is not known by whom. Patton, a prominent local farmer and landowner, bought the property as a young man a quarter-century later. It assumed its present form after several additions and renovations in the first 40 years of its existence. In 2008 it was listed on the National Register of Historic Places.

Vails Gate is a hamlet (and census-designated place) in Orange County, New York, United States. The population was 3,368 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. Vails Gate is in the southern part of the Town of New Windsor, located on Route 32. It is defined largely by the junction of that highway with Routes 94 and 300, a busy commercial center which has the ZIP code 12584. Part of that also spills into adjacent regions of the Town of Cornwall to the south.

The John Haskell House, also known as the Hermitage, was a historic home located in New Windsor, Orange County, New York. It was built about 1726, and was a 2+1⁄2-story log dwelling with a rear ell. It had a gabled roof and large interior chimney at each end. Due to its construction, the Haskell House was considered one of the largest intact log mansions in the Thirteen Colonies.

Lake Washington is the primary reservoir for the city of Newburgh, New York, United States. It is located just southwest of the city, lying partially within it and the neighboring towns of Newburgh and New Windsor. It holds approximately 1.5 billion US gallons (5,700,000 m3), an amount equivalent to the city's annual consumption.Recreational facilities such as picnic grounds are accessible to the public at Masterson Park, near the reservoir's spillway along NY 207.

Knox's Headquarters State Historic Site, in the town of New Windsor in Orange County, New York, consists of the Georgian house of the Ellison family, built in 1754 by immigrant William Bull of Hamptonburgh, NY, and the grounds around it. The site is located on Old Forge Hill Road, just south of Route 94 east of Vails Gate. Although most closely associated with Henry Knox, who used it as his headquarters as the Revolutionary War drew to a close in the early 1780s, it was used as a general's headquarters throughout most of the war, by Nathanael Greene and Horatio Gates. The site was declared a National Historic Landmark in 1972. While owned by the New York State Office of Parks, Recreation and Historic Preservation the Ellison House is administered and operated by the Palisades Interstate Park Commission, like many other state parks and historic sites in the mid and lower Hudson region. Today, the house can be toured when the site is open. It is used to educate visitors about how 18th-century families such as the Ellisons actually lived. On holidays and special occasions staff dress in reproduction period clothing and give special events. Staff dressed as the 2nd Continental Artillery frequently demonstrate cannon use on the grounds during special events, as Knox was best known for his command of Continental artillery. The house and its grounds were the setting and subject of the children's haunted-house novel Buried Treasure (1919), by the best-selling children's author Henry Everett McNeil. The book is illustrated with McNeil's own photographs (made circa 1911 or 1912) of the various buildings and bridge at the Knox site. The Jane Colden Plant Sanctuary along some of the trails in the nearby woods memorializes America's first female botanist, who also resided in the area.

The Edmonston House is located on NY 94 in the Vails Gate section of the Town of New Windsor in Orange County, New York. It has been listed on the National Register of Historic Places since 1979.

Browns Pond, in the Town of New Windsor in Orange County, New York, United States, is the smaller of two reservoirs for the nearby City of Newburgh. The 0.3 square mile pond is hook-shaped, with the circuitous Mount Airy Road running past both ends.Its outlet streams ultimately feed Silver Stream, which is a tributary of the Moodna Creek. The Catskill Aqueduct, which the city uses as a supplementary supply, runs between the two. Unlike Lake Washington, there are no recreational facilities on the reservoir.

The Woodruff House is located on NY 32 in Cornwall, New York, United States, a short distance south of the hamlet of Vails Gate. It is a small stone building dating to the early 19th century. It is one of the few remaining stone houses from that period of the town's history. It was listed on the National Register of Historic Places in 1996.

Cornwall Central High School is the high school serving the Cornwall Central School District in Orange County, New York. It draws students from portions of three towns: Cornwall, New Windsor, and Woodbury, as well as the village of Cornwall-on-Hudson. While it is in the New Windsor ZIP Code, it is located off NY 94 just inside the Cornwall town line.

Woodlawn Cemetery is a historic cemetery in New Windsor, New York exemplifying the rural style. For more than a century, a private organization maintained it, until the Town of New Windsor took ownership in 2017.

The Firthcliffe Firehouse is located along Willow Avenue in the Town of Cornwall in Orange County, New York, United States. It was built to protect the homes being built by the Firth Carpet Company for workers at its nearby plant in the early 20th century. In 1996 it was added to the National Register of Historic Places. It is currently being used as a hair salon.