Tweddle Farmstead

The Gideon Pelton Farm is a Registered Historic Place located on Rockafellow Lane in the Town of Montgomery in Orange County, New York. Pelton settled the area in the 1770s and built the house soon afterwards. A stone wing was built on it before the end of the century, and in the 1830s a large frame section was added in the then-popular Greek Revival style that gave the house its current character. It continues to be used as a farmhouse to this day.It was added to the National Register of Historic Places in 1995.

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 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 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 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.

The African-American Cemetery, known historically as the Colored Cemetery, in the town of Montgomery, New York, United States, holds the graves of roughly 100 humans, mostly believed to be African slaves who were brought over by the earliest settlers of the region from the Rhenish Palatinate in the mid-18th century. It is located on NY 416 a tenth of a mile (160 m) north of the Interstate 84 crossing, near the Wallkill River. All the originally marked graves that have been identified have had the stones used to mark them supplemented with small pipes. Only two have any kind of discernible inscription, one of which dates its occupant's passing to 1756. The site had grown neglected until the town and private donors undertook to fix it up in the early 1990s. It was fully restored and rededicated, with a new wooden fence and explanatory plaque, in 1995. It was added to the National Register of Historic Places in 1996.

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 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 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.

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.

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