Goosepond Mountain State Park

Walton Park is a census-designated place (CDP) in Orange County, New York, United States. As of the 2020 census, the CDP had a total population of 3,907. Walton Park is on the town line separating the towns of Chester and Monroe. Street addresses within Walton Park are usually assigned to Monroe, not Chester.

Chester is a village in Orange County, New York, United States. The population was 3,993 at the 2020 census. It was named after the City of Chester in the Cheshire region of northwest England. Chester 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 of Chester is primarily located in the northern part of the Town of Chester.

Chester is a town in Orange County, New York, United States. The population was 12,646 at the 2020 census. Chester contains a village, also called Chester. Chester is the birthplace of Philadelphia-style cream cheese.

The Yelverton Inn and Store is a group of four historical buildings in Chester, New York, United States. Located on NY 94 where the highway turns from Main to Academy Street,. The complex includes the original 1765 inn, its barn and shed, and the 1841 store, known locally as Durland's. The latter building is a rare surviving example of a Greek Revival commercial building. Both the Inn and store have been local landmarks in Chester for many years, and were added to the National Register of Historic Places in 1980. The buildings, which hosted Alexander Hamilton, Aaron Burr and George Washington at different times, are well-preserved examples of their periods and architectural styles.

The First Presbyterian Church of Chester is a Presbyterian church in Chester. It is located along NY 94 in the eponymous village in Orange County, New York, United States. The current church building, listed on the National Register of Historic Places in 1998, is the third in the history of the congregation, on as many locations. Two additions have been built but the building otherwise remains intact, a well-preserved example of a 19th-century rural American church.

Fury Brook Farm, also Bairdlea Farm, is located on King's Highway in the Town of Chester, New York, United States, just north of the hamlet of Sugar Loaf. It was listed on the National Register of Historic Places in 2004 to help protect the land around it from development.It was established in 1731, the first farm on the Wawayanda Path, which King's Highway follows. Several decades later many of the horses used by the Continental Army during the Revolutionary War were bred and raised on its pastures.

Chester Academy is a public secondary school located in Chester, New York, United States. Their mascot is the Hambletonian, after Hambletonian 10, a famed harness racing horse that is an ancestor of nearly every Standardbred horse in the United States. The school's colors are orange and blue and . Chester Academy is a recently built school, with construction starting in 2002. Students moved into the school from Chester Junior/Senior High School, located about 0.741 miles away, in 2004. There are three floors. The school offers a variety of sports at different levels: football, soccer, baseball, cheerleading, Wrestling and basketball at varsity and junior varsity levels, as well as a varsity track and cross country team. They also have volleyball as of 2015. In 2012, Chester Academy was the first school in Hudson Valley to send home 1-to-1 Google Chromebooks with its students under a plan from K-12 Director of Instruction & Technology / Data Administrator Edward A. Spence. In 2014, Chester UFSD was awards an "Innovative Schools" annual award from NYSSBA. The district has since had ten different school districts visit Chester Academy to share best practices with Mr. Spence, teachers and students regarding their award-winning 1-to-1 Chromebook Instruction Plan. Take-home 1-to-1 Chromebooks have since become the de facto standard for school districts. The name of the school changed from Chester Jr/Sr High School to Chester Academy in May 2004 when students and faculty were moved from the original Maple Avenue school building to the new building on Hambletonian Avenue. Chester Jr/Sr High School housed students grades 7–12, and was changed to accommodate students grades 6–12 in the Chester Academy. The school building is separated into a junior high school wing and a high school wing. Chester Academy is also home to an Orange-Ulster BOCES Special Education wing. One memorable event in the school's history was a school shooting scare in 2018. A BOCES student made a 911 call claiming that a man with a gun was in the building. What ensued was a three-hour lockdown as SWAT members swept each room of the building. Other schools in the area had a lockout, and once the truth was uncovered, no charges were pressed on the student.

Sugar Loaf is a mixed-use hamlet in Orange County, New York, United States. It is located in the Town of Chester, within view of Sugar Loaf mountain.

Black Meadow Creek is a 9.7-mile-long (15.6 km) tributary of the Otter Kill in Orange County, New York, in the United States. Via the Otter Kill, it is part of the Moodna Creek watershed, flowing onward to the Hudson River, in one of New York State's most biodiverse natural areas. Home to 13 species of salamander as well as to New York's largest population of the Northern Cricket Frog (Acris c. crepitans), the state's only listed "Endangered" frog species, the creek area is considered by biologists to be one of the state's herpetological "hot spots". Black Meadow Creek has several confirmed bald eagle nests along its length.Roughly 1/2 of the creek's length runs through a reservoir preserve owned by Orange County. This preserve status is credited with maintaining the upper creek's floodplain in its natural state for over one century. Black Meadow Creek begins in the town of Warwick, near Glenmere Lake, and flows north into the town of Chester before converging with the Otter Kill in the village of Chester. Studies of the creek and its watershed are conducted by the nonprofit Sugar Loaf Historical Society and the nonprofit Glenmere Conservation Coalition, which maintain a small launch and study area on the creek.The creek was named for the expansive, dark, forested swamp that settlers found along its floodplain, most of which was transformed into agricultural areas by the mid 19th century. Its floodplain hosts the Black Meadow Hunting Club, the Straub Farm and the Chester Industrial Park at its confluence with the Otter Kill.

Monroe is a town in Orange County, New York, United States. The population was 21,387 at the 2020 census, compared to 39,912 at the 2010 census; the significant fall in census population was due to the secession of the town of Palm Tree in 2019. The town is named after President James Monroe.

Monroe is a village in Orange County, New York, United States. The population was 9,343 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 community is not named after President James Monroe, but rather after an early 19th-century New York state senator. The Village of Monroe is in the northwestern part of the Town of Monroe by NY Route 17 (soon to be Interstate 86) and US 6. NY 17M is its main street.

The Village of Monroe Historic District, also known as the Smith's Mill Historic District, is located in Monroe, New York, United States. It is an irregularly shaped 81-acre (33 ha) area containing 36 properties, primarily residential but with some churches and commercial buildings, in the center of the village, just east of its downtown. In 1998 it was listed on the National Register of Historic Places. Most of the district is open space, taken up by a mill pond and park, a cemetery and the former site of a racetrack. Its buildings, mostly from the 19th century but some predating the Revolution, are clustered in a small area Stage Road and represent the early core of Monroe from the days when Smith's Mill, its first business, had dammed the waters of Ramapo Creek. They are also survivors of an 1892 fire that devastated the village. The Greek Revival and Federal architectural styles prevail, with some mid-19th-century Gothic Revival homes included. Among the contributing properties are the oldest Masonic Lodge in New York, and the home of David Smith, the village's first settler.