Gideon Pelton Farm

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 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 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 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.

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 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.

Bodine's Bridge carries New York State Route 211 across the Wallkill River, a mile (1.6 km) south (west by the highway's signed direction) of the village of Montgomery, New York, United States, near Orange County Airport. At 340 feet (103 m) in length, the steel through truss is the longest bridge along Route 211. The current bridge was built in 2015. Its predecessor dated to 1933, with a reconstruction in 1970. All the bridges at the location have been named after nearby, still-standing Bodine's Tavern, a popular rest stop on the early 19th century Minisink to Montgomery Turnpike, which later became Route 211. The house, now listed on the National Register of Historic Places, was built near a popular ford along the river, which the bridges were built over. Due to the bridge's location in the river's flood plain, it is often closed after heavy rains when its approaches, particularly to the south, are overrun by rising waters. This happened most recently during the April 2007 Nor'easter.In summer 2015 the state Department of Transportation began replacing the bridge. Route 211 was closed through the bridge at the beginning of June; traffic was detoured via Goshen Turnpike (County Route 101) in the Town of Wallkill through the hamlet of Scotchtown to State Route 17K via Scotchtown–Collabar Road (County Route 47). The new bridge, completed and opened in September of that year, has three continuous spans, two 12-foot (3.7 m) travel lanes and 6-foot (1.8 m) shoulders. The project was estimated to have cost $8.1 million; it is being paid for by a Federal Emergency Management Agency grant program to replace old scour-prone bridges in areas subject to frequent flooding.

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.

New York's Orange County Airport (IATA: MGJ, ICAO: KMGJ, FAA LID: MGJ) is an untowered airport located one nautical mile (2 km) southwest of the village of Montgomery, in the Town of Montgomery, United States, at the junction of state highways 211 and 416. It is owned and operated by Orange County. It is included in the National Plan of Integrated Airport Systems for 2011–2015, which categorized it as a general aviation facility.It is a popular place for aspiring local pilots to learn to fly or practice their skills. With 125,000 takeoffs and landings annually, it was New York's second-busiest general-aviation airport in 2006.Transmissions between pilots and the airport are rebroadcast on a one-watt station at 88.1 megahertz, so it is possible to tune into them on a standard car radio while driving in the vicinity.The airport's low traffic and out-of-the-way location have made it a popular place to store private jets. In 2006 county officials were reported to be working on a deal with a local developer to build 10 private luxury hangars to cater to what they saw as a growing market and raise money for the airport without raising taxes.

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.