John A. Crabtree House

The Montgomery Worsted Mills, known today as Montgomery Mills, is along the Wallkill River at the end of Factory Street in the Orange County village of Montgomery, New York. It was one of the earliest efforts to harness the river for industrial purposes. Founders Arthur Patchett and William Crabtree became prosperous and upstanding citizens who left their mark on the community they lived in. Many of the homes on the nearby stretch of Factory Street were built by them for their family, and their descendants still live in the Montgomery area. The mills are still in operation too, but are no longer property of the family or used to mill textiles. While they sell yarn, today the mill is primarily an electric power generation station. A deal is in the works to make it a City Winery.

The Patchett House is located at Ward Street (NY 17K), on the junction with Factory Street, in Montgomery, New York. It was originally built in the early 19th century as a tavern serving travelers on the Newburgh–Cochecton Turnpike, whose eastern half 17K follows today. Arthur Patchett, at the time co-owner of the Montgomery Worsted Mills at the end of Factory Street on the Wallkill River, moved into the house sometime in the 1890s. His family continued living there until the 1970s. The house was added to the National Register of Historic Places in 1980. Later on, though, it remained vacant and by the end of the century had fallen into serious neglect and disrepair. In 2005, serious renovations were undertaken and today the house looks as good as new. The most recent tenants are the nonprofit artist's environmental cooperative Wallkill River School. A nearby townhouse complex is named Patchett Crossing. The Montgomery Water Works, built on land originally owned by the Patchetts, stands almost just across 17K, and the Orange County Choppers production facility is just up the street.

The Montgomery Water Works is located along NY 17K in the village of Montgomery, New York. The two small brick buildings were built in 1895 on land sold to the village by Arthur Patchett, whose own house still stands across the road. It was added to the National Register of Historic Places in 2005. As of 2007 a new senior housing development has been built near the water works. Workers had to take care to avoid damage to the building.

The Peale's Barber Farm Mastodon Exhumation Site, near Montgomery, New York, is the site of an 1801 exhumation of a mastodon which became "the world's first fully articulated prehistoric skeleton". The exhumation was led by artist/scientist Charles Willson Peale.The site was listed on the U.S. National Register of Historic Places on October 20, 2009. The listing was announced as the featured listing in the National Park Service's weekly list of November 6, 2009.The mastodon skeleton is exhibited at the Hessisches Landesmuseum Darmstadt in Darmstadt, Germany, though it was returned to the US for a temporary exhibit at the Smithsonian American Art Museum.

The Daniel Waring House, also known as Indian Hill, is located on River Road (Orange County Route 29) just outside the village of Montgomery, New York, United States. It sits on a large parcel of land overlooking the Wallkill River at the junction of River Road and NY 17K, just opposite the western approach to Ward's Bridge. It is believed that part of the house dates to the 18th century. Waring, a later resident, had the four-column temple-style Greek Revival front section built in the 1840s. It has been occupied since his time and remains a private residence. In 1995 it was listed on the National Register of Historic Places, along with several other buildings and structures on the property. The current resident, a former town supervisor, purchased the property from Richard James and Dora Holvey in 1998.

Valley Central High School is located in Montgomery, New York. It educates students in grades 9-12 in the Valley Central School District, which includes much of the town of Montgomery, portions of neighboring Wallkill and Newburgh and the three villages of Maybrook, Montgomery and Walden as well as parts of Campbell Hall and Coldenham.

Montgomery is a village located in Orange County, New York, United States. Located 60 miles (97 km) northwest of New York City, and 90 miles (140 km) southwest of Albany, this quaint community is an historical and cultural hub of the Hudson Valley region and has grown in the last 30 years to become an outer-ring commuter suburb within the New York metropolitan area. The population was 3,834 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. The village is named after General Richard Montgomery, an officer of the American Revolution. The Village of Montgomery is inside the Town of Montgomery.

Ward's Bridge carries NY 17K across the Wallkill River at the western end of the village of Montgomery in Orange County, New York, United States. It is named, as its predecessors were, for James Ward, an early settler in the area who established his grist mill on what is now the village side and built the first bridge in the mid-18th century. Originally, Montgomery was even called Ward's Bridge, and today a nearby restaurant calls itself the Ward's Bridge Inn.The mill has long since been demolished, but the earliest buildings in the village that were built around it still stand and are now the Bridge Street Historic District, listed on the National Register of Historic Places. Another Registered Historic Place, the Daniel Waring House, is located at the corner of 17K and River Road on the western side. The current bridge, a steel through truss, is 231 feet (70 m) long, with a 22-foot (6.7 m) roadway and small sidewalk on the eastern (downriver) side. It was built in 1940, and renovated in 1982.

The Union Street–Academy Hill Historic District makes up most of downtown Montgomery, New York, United States. It abuts the smaller Bridge Street Historic District to the northwest. The district has been on the National Register of Historic Places since November 21, 1980. The district is roughly bounded by Hanover Street, one block west of Union Street (NY 211), Ward Street (NY 17K) on the north, Wallkill Avenue to the east and Sears Street to the south. The 300-acre (1.2 km2) rectangle-shaped historic district contains 83 buildings, many of them houses that date to the early and mid-19th century and exemplify popular contemporary architectural styles. The centerpiece of the historic district is the Village Hall, the former Montgomery Academy, which dates to the 1830s. Its location on a slight rise gave its name to the rise and, later, the historic district.

The Bridge Street historic district is the smaller of two that make up the downtown area of the village of Montgomery in Orange County, New York. It is located along Bridge Street, just off NY 17K as it enters the village by crossing the Wallkill River at Ward's Bridge, hence its name. The Union Street-Academy Hill Historic District is located immediately to the southeast. The district is primarily residential. Its 28 houses are generally older than their counterparts in the larger district, with the oldest dating to 1792. It was added to the National Register of Historic Places in 1980.

Milliken-Smith Farm is a historic home and farm complex located at Montgomery in Orange County, New York. Contributing buildings include the Milliken-Smith house (built in 1770 and expanded about 1870), a large timber-frame barn dated to the 18th century, a light frame chicken house (c. 1900), and a banded wood storage silo. The earliest portion of the house is a 1+1⁄2-story timber-frame building. It was expanded during the 1870s with a 2-story light frame addition. A non-historic addition was completed in 1962.It was listed on the National Register of Historic Places in 2009.

Peachcroft, sometimes referred to as the James Wilson Brown House, is located along River Road (Orange County Route 29) between Walden and Montgomery in the Town of Montgomery, New York, United States. It is built in a combination of the Federal and Queen Anne architectural styles. The former came from Brown, the original builder of the house; the latter from renovations by the Millspaugh family, who moved in in the later 19th century and established many businesses, among them a furniture store still in business Walden. Peachcroft remains the center of a working farm of almost a hundred acres that backs on the Wallkill River. In 1994 it and three outbuildings were listed on the National Register of Historic Places.