Bull's Bridge

The Ten Mile River (Tenmile River on federal maps) is a 15.4-mile-long (24.8 km) river that flows through Dutchess County, New York, into westernmost Connecticut. The river is formed in the town of Amenia, New York, at the confluence of Webatuck Creek and Wassaic Creek. The Ten Mile River runs south through the town of Dover, New York before turning east and crossing into Connecticut, where it forms the boundary between the towns of Kent and Sherman for one-half mile before flowing into the Housatonic River. This is a popular whitewater paddling destination with mostly quickwater and a few whitewater areas reaching up to Class III.

South Kent School, a private all-boys boarding school in South Kent, Connecticut, United States, is located on a 650-acre (2.6 km2) campus in western Litchfield County. It is sited on Spooner Hill east of Bull's Bridge, overlooking the former Housatonic Valley rail-line, Hatch Pond, and the 'whistle-stop' South Kent station, and is itself overlooked by Bull Mountain. The school has an operating budget of approximately $14 million and a staff of less than 100. From its inception, South Kent School was intended to offer a service-oriented education "at minimum cost for boys of ability and character, who presumably on graduation must be self-supporting. " Its motto is "Simplicity of life, Self-reliance, and Directness of purpose".

South Kent is a village located in Litchfield County, Connecticut, United States, alongside the border with New York, and within and part of Kent, Connecticut. South Kent has its own Post Office whose ZIP code is 06785. South Kent is also home to South Kent School, a private prep school.

Gaylordsville is a village (neighborhood/borough) in the northwest corner of the town of New Milford, Litchfield County, Connecticut, United States. It was listed as a census-designated place (CDP) prior to the 2020 census.

The Merwinsville Hotel is a historic hotel building and former railroad station at 1 Brown's Forge Road in the Gaylordsville village of New Milford, Connecticut. Built in 1842-43, it is one of the oldest hotels built specifically for a railroad stop in the United States. It was listed on the National Register of Historic Places in 1977.

Gaylordsville station is a former train station in Gaylordsville, Connecticut. The station building was built in the 1918, replacing the Merwinsville Hotel as the local depot, to serve passengers on the Housatonic Railroad. Shortly after its closure, the station was purchased by former New York advertising executives, Jean & Cle Kinney. In October 1971, the couple relocated the structure to a nearby hill on River Road and converted it into their own unique and creative home.

Kent School is a private, coeducational, college preparatory boarding school in Kent, Connecticut, established by Frederick Herbert Sill in 1906. It is affiliated with the Episcopal Church of the United States. It has a long history as an "elite school, not a school for elites," and innovated the sliding-scale tuition model in the early 20th century.

The Litchfield Jazz Festival began in 1996 at the White Memorial Conservation Center in Litchfield Hills in Connecticut. The parent organization that runs the festival is Litchfield Performing Arts, Inc, a not-for-profit founded in 1981. After two years at the White Memorial Conservation Center the festival moved to the Goshen Fairgrounds in Goshen, Connecticut, where it was held until 2008. The festival moved to the grounds of Kent School in Kent, Connecticut in 2009, and was held there until 2011. In 2012 the festival returned to the Goshen Fairgrounds in Goshen, CT.

Ore Hill is a restaurant in Kent, Connecticut. Established in April 2023, the business was included in The New York Times's 2023 list of the 50 best restaurants in the United States.

Kent station is a former train station in Kent, Connecticut. The station building was built in the 1870s to serve passengers on the Housatonic Railroad. The depot was anticipated to be completed and operating by August 1, 1872. However, by April 1873 only the foundation and a portion of the framework was completed. Once completed, the depot was described as "one of the finest" on the Housatonic RR.The structure still stands today and operates as Kent Station Pharmacy.

Wingdale is a hamlet and census-designated place (CDP) in the town of Dover in Dutchess County, New York, United States. It was first listed as a CDP prior to the 2020 census.The community is in southeastern Dutchess County, in the southern part of Dover. The hamlet of Wingdale is in the northern part of the CDP, while the Evangelical Center is in the south, on the grounds of the former Harlem Valley State Hospital, and scattered housing occupies the hills in the eastern part of the CDP. The Swamp River, a north-flowing tributary of the Tenmile River, part of the Housatonic River watershed, runs through the center of the CDP. New York State Route 22 runs through the CDP, passing east of Wingdale hamlet. The highway leads north 7 miles (11 km) to Dover Plains and south the same distance to Pawling. State Route 55 runs concurrently with NY 22 to the south, but turns east at Wingdale and leads 6 miles (10 km) to Gaylordsville, Connecticut. Wingdale is 21 miles (34 km) east of Poughkeepsie and 23 miles (37 km) northwest of Danbury, Connecticut. The Metro-North Harlem Valley–Wingdale station is located between the Evangelical Center and the Harlem Valley Golf Course in the southern part of the CDP.

Dover is a town in Dutchess County, New York, United States. The population was 8,415 at the 2020 census. The town was named after Dover in England, the home town of an early settler. The town of Dover is located on the eastern boundary of the county, north of Pawling, south of Amenia, and west of the state of Connecticut.