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Brattleboro (), originally Brattleborough, is a town in Windham County, Vermont, United States. The most populous municipality abutting Vermont's eastern border with New Hampshire, which is the Connecticut River, Brattleboro is located about 10 miles (16 km) north of the Massachusetts state line, at the confluence of Vermont's West River and the Connecticut. As of the 2020 Census, the population was 12,184. There are satellite campuses of three colleges in Brattleboro: Community College of Vermont, Union Institute and University, and Vermont Technical College. Locate in Brattleboro are the New England Center for Circus Arts, Vermont Jazz Center, and Brattleboro Retreat, a mental health and addictions center.

The Creamery Covered Bridge is a historic covered bridge in West Brattleboro, Vermont. Now closed to traffic, the Town lattice truss bridge formerly carried Guilford Road across Whetstone Brook, just south of Vermont Route 9. Built in 1879, it is Brattleboro's last surviving 19th-century covered bridge.

The William Harris House, also known locally as the Joseph Caruso House, is a historic house on Western Avenue in Brattleboro, Vermont. Built in 1768, this Cape-style house is believed to be the oldest surviving building in the town, and one of the oldest in the entire state. It was listed on the National Register of Historic Places in 1978.

The Austine School for the Deaf, now closed, in Brattleboro, Vermont, was an independent, coeducational day and residential school for deaf and hard-of-hearing children age four to eighteen from New England and New York.

Estey Organ Company was an organ manufacturer based in Brattleboro, Vermont. The company was founded in 1852 by Jacob Estey, who bought out another Brattleboro manufacturing business. At its peak, the company was one of the world's largest organ manufacturers, employed about 700 people, and sold its high-quality items as far away as Africa, Great Britain, Australia, and New Zealand. Estey built around 500,000 to 520,000 pump organs between 1846 and 1955. Estey also produced pianos, made at the Estey Piano Company Factory in New York City.

The Samuel Gilbert Smith Farmstead is a historic farm property at 375 Orchard Street in Brattleboro, Vermont. The present 20-acre (8.1 ha) property includes a well-preserved 1870s-era connected farmstead and other 19th-century landscape features. Associated with the property are a well-documented history of the transformations the property has undergone since its 18th-century origins. The property was listed on the National Register of Historic Places in 2000.

Harris Hill Ski Jump is a ski jump in Brattleboro VT. The event hosts annual ski jumping competitions. The original jump was built in 1922, and was closed for renovation in 2005. The jump was reopened in 2009 after a $600,000 renovation.The jump is designed around the international standards for ski jumps, reaching an Olympic-calibre 90 meter length. The jump has hosted 9 national championships and the Olympic Qualifier events.

Brattleboro Memorial Hospital, is a hospital in Brattleboro, Vermont. Brattleboro Memorial Hospital is a community hospital which has been serving greater Brattleboro and the tri-state area since 1904. The BMH Medical Staff claims to employ more than 130 board-certified physicians, active in both primary care and many specialties.

The West Brattleboro Green Historic Districts encompasses the historic core of the village of West Brattleboro, Vermont. Centered in the triangular green at South Street and Western Avenue, it includes a modest collection of buildings constructed between about 1800 and 1910. It was listed on the National Register of Historic Places in 2002.

Brattleboro is a census-designated place (CDP) corresponding to the densely populated core of the town of Brattleboro in Windham County, Vermont, United States. The population was 8,289 at the 2000 census.

The Lewis Grout House is a historic house on Western Avenue at Bonnyvale Road in West Brattleboro, Vermont. Built in about 1880 for a widely traveled minister, it is a well-preserved and somewhat late example of Gothic Revival architecture. It was listed on the National Register of Historic Places in 1996.

The Homestead–Horton Neighborhood Historic District encompasses a small turn-of-the-20th century neighborhood area in Brattleboro, Vermont. Located on a portion of Canal Street and all of Horton and Homestead Places, the district includes a significant number of Queen Anne Victorians, as well as the Italianate home of Jacob Estey, proprietor of the Estey Organ Company, one of the city's larger employers. The district was listed on the National Register of Historic Places in 2009.