Union Street–Academy Hill Historic District

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.

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.

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 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.

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 John A. Crabtree House is a historic house located at 15 Factory Street in the village of Montgomery, Orange County, New York.

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.

Muddy Kill is a 4.2-mile-long (6.8 km) tributary of the Wallkill River that runs entirely through the town of Montgomery in Orange County, New York, United States. It rises from a small pond just over a mile (1.7 km) west of the village of Walden, flowing first southwesterly then roughly due south to empty into the Wallkill just upstream from the village of Montgomery. Its course takes it mostly through areas cleared for agriculture, although not all are presently cultivated. Near its mouth it passes through a large horse farm, and then once it runs through a culvert under NY 17K it is within 102 acres (41 ha) recently acquired and developed by the town as Benedict Farm Park. It drains the low-lying Comfort Hills to the west. The name is an English interpretation of Modder Kill, as it was called by early Dutch settlers in the region. In Dutch, Modder means "mud" or "slime", so the meaning of the creek's name stayed the same. The fertile lands of the creek's valley attracted many early settlers, and the houses of some, such as Abraham Dickerson, Jacob Bookstaver, Moses Mould and Wilhelm Schmitt, still stand. It has been equally attractive to contemporary real estate developers, and to lessen environmental impacts on the stream and the Wallkill watershed as a whole the Open Space Institute and the town cooperated in 2005 to obtain a permanent agricultural easement on the 227-acre (92 ha) Zylstra Farm, one of the largest properties along the creek. With little significant woodland in its valley, the creek can rise quickly when heavy rains fall. After the April 2007 Nor'easter, it flooded severely enough near its mouth that Route 17K had to be closed west of Montgomery for two days.

The Harrison Meeting House Site and Cemetery, also known as the Germantown Church Site and Cemetery or just the Germantown Cemetery, is located on New York State Route 416 (NY 416) right at its northern terminus with NY 211, across from Orange County Airport just outside the village of Montgomery, New York.The first settlers of what would eventually become the Town of Montgomery came here and built their church on this site in the early 18th century. It would later be surrounded with their houses. The church no longer stands, but several of those early settlers are buried within the stone wall around the site. The Town of Montgomery has taken possession after the site was restored from past neglect and added a small interpretive plaque. It was added to the National Register of Historic Places in 1998.

The Tweddle Farmstead is a Registered Historic Place located on Beaverdam Road in the Town of Montgomery in Orange County, New York. Built in the early 19th century by Bercoon van Alst, it was added to significantly in the 1830s in the Greek Revival style. This gave the house its current front. Thomas Tweddle bought the house in 1868, and it has remained in his family since.It was added to the National Register of Historic Places in 1999.

The Johannes Miller House is a Registered Historic Place in the Orange County, New York, Town of Montgomery. It is located on NY 211 just opposite its junction with NY 416 and another Registered Historic Place, the Harrison Meeting House Site and Cemetery. Orange County Airport is nearby. It was built originally as a Georgian in 1771 by Hans Smith, one of the early German settlers of the town. Twenty years later, Miller, a prosperous local businessman, acquired it and rebuilt it in the Federal style. In 1835, his descendants added some Greek Revival elements.