Western Connecticut Planning Region, Connecticut in the context of Greater Danbury

The Connecticut panhandle is the southwestern appendage of Connecticut, where it abuts New York State. It is contained entirely in Fairfield County and the Western Connecticut Planning Region, and includes all of Greenwich, Stamford, New Canaan, and Darien, as well as parts of Norwalk and Wilton. It has some of the most expensive residential real estate in the United States.

The irregularity in the boundary is the result of territorial disputes in the late 17th century between the British colonies of New York and Connecticut. In an agreement on November 28, 1683, that established the New York–Connecticut border as 20 miles (32 km) east of the Hudson River, New York gave up its claim to this area of 61,660 acres (249.5 km) east of the Byram River, whose residents considered themselves part of Connecticut. In exchange, New York received an equivalent area consisting of a 1.81-mile-wide (2.91 km) strip of land known as the "Oblong" running northwards from Ridgefield, Connecticut to the Massachusetts border, alongside the New York counties of Westchester, Putnam, and Dutchess. New York was also given undisputed claim to Rye, New York.

Greenwich (/ˈɡrɛnɪtʃ/ GREN-itch) is a town in southwestern Fairfield County, Connecticut, United States. As of the 2020 census, it had a population of 63,518. It is the largest town on Connecticut's affluent Gold Coast. Greenwich is home to many hedge funds and financial services firms due to its residential setting and proximity to Manhattan.

Greenwich is a principal community of the Bridgeport–Stamford–Norwalk–Danbury metropolitan statistical area, which comprises all of Fairfield County, and is part of both the greater New York metropolitan area and the Western Connecticut Planning Region. The town is the southwesternmost municipality in both the State of Connecticut and the six-state region of New England. The town is named after Greenwich, a royal borough of London in the United Kingdom.

Stamford (/ˈstæmfərd/) is a city in Fairfield County, Connecticut, United States, 34 miles (55 kilometers) outside of New York City. It is the sixth-most populous city in New England. Stamford is also the largest city in the Western Connecticut Planning Region, and Connecticut's second-most populous city, behind Bridgeport. With a population of 135,470, Stamford passed Hartford and New Haven in population as of the 2020 census. It is in the Bridgeport–Stamford–Danbury metropolitan statistical area, which is part of the New York City metropolitan area (specifically, the New York–Newark, NY–NJ–CT–PA Combined Statistical Area).

As of 2023, Stamford is home to eight Fortune 500 companies and numerous divisions of large corporations. This gives it the largest financial district in the New York metropolitan region outside New York City and one of the nation's largest concentrations of corporations. Dominant sectors of Stamford's economy include financial management and real estate, tourism, information technology, healthcare, telecommunications, transportation, and retail. Its metropolitan division is home to colleges and universities including UConn Stamford and Norwalk Community College.

Westport is a town in the Fairfield County, Connecticut, United States. Located in the Gold Coast along the Long Island Sound, it is 48 miles (77 km) northeast of New York City and is part of the Western Connecticut Planning Region.

New Canaan (/ˈkeɪnən/) is a town in Fairfield County, Connecticut, United States. The population was 20,622 according to the 2020 census. The town is part of the Western Connecticut Planning Region.

About an hour from New York City by train, the town is considered part of Connecticut's Gold Coast. The town is bounded on the south by Darien, to the west by Stamford, on the east by Wilton, on the southeast by Norwalk, and on the north by Lewisboro and Pound Ridge in Westchester County, New York.

Wilton is a town in Fairfield County, Connecticut, United States. As of the 2020 census, the town population was 18,503. The town is part of the Western Connecticut Planning Region.

Officially recognized as a parish in 1726, Wilton is a residential community with open lands, historic architecture such as the Round House, and many colonial homes. Many residents commute to nearby cities such as Stamford or New York City.

Ridgefield is a town in Fairfield County, Connecticut, United States. Situated in the foothills of the Berkshire Mountains and on the New York state border, Ridgefield had a population of 25,033 as of the 2020 census. The town is part of the Western Connecticut Planning Region. The town center, which was formerly a borough, is defined by the U.S. Census Bureau as a census-designated place. The town was settled then quickly incorporated by 1709.

Danbury (/ˈdænbɛri/ DAN-berr-ee) is a city in Fairfield County, Connecticut, United States, located approximately 50 miles (80 km) northeast of New York City. Danbury's population as of 2020 was 86,518. It is the third-largest city in Western Connecticut, and the seventh-largest city in Connecticut. Located within the heart of the Housatonic Valley region, the city is a historic commercial hub of western Connecticut, home to many commuters and summer residents from the New York metropolitan area and New England.

Danbury is nicknamed the "Hat City", because it was once the center of the American hat industry, during the nineteenth and early twentieth centuries. The mineral danburite is named after Danbury, while the city itself is named for Danbury in Essex, England.