Samuel Gilbert Smith Farmstead

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 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.

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 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.

WINQ (1490 AM; "WINK Country") is a radio station licensed to serve Brattleboro, Vermont. The station is owned by the Monadnock Broadcasting Group subsidiary of Saga Communications and licensed to Saga Communications of New England, LLC. WINQ simulcasts the country music programming of Keene, New Hampshire sister station WINQ-FM. The station had previously been assigned the WKVT call letters by the Federal Communications Commission. WKVT was part of a network of progressive talk stations throughout the northeastern United States that are owned by Saga Communications (others including WNYY in Ithaca, New York, WHMP in Northampton, Massachusetts, WHNP in East Longmeadow, Massachusetts and WHMQ in Greenfield, Massachusetts); these, in turn, were among the last progressive talk stations still on the air in early 2017. Because of the migration of most progressive talk shows to off-air platforms, Saga announced plans to begin dropping the format in February 2017; WNYY was the first to change, followed by WHNP, with most of the other stations in the network likely to follow.On May 30, 2018, WKVT dropped its syndicated programming, including Stephanie Miller and Thom Hartmann, and began to carry the country music programming of Keene-based WINQ; WKVT's local morning drive time program, Green Mountain Mornings, was retained following the format change. The station changed its call sign to WINQ on June 19, 2018. Green Mountain Mornings, which was hosted by Olga Peters, was cancelled in December 2018.

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.

West Brattleboro is a census-designated place (CDP) in the town of Brattleboro, Vermont, United States. The population was 3,222 at the 2000 census.

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.

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.

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 Brattleboro Retreat is a private not-for-profit mental health and addictions hospital that provides comprehensive inpatient, partial hospitalization, and outpatient treatment services for children, adolescents, and adults. Located just north of downtown Brattleboro, Vermont, United States, the Retreat is situated on approximately 300 acres of land along the Retreat Meadows inlet of the West River. Founded in 1834, the retreat was "the first facility for the care of the mentally ill in Vermont, and one of the first ten private psychiatric hospitals in the United States". It is considered a pioneer in the field of mental health care in the United States. The retreat is a member of the Ivy League Hospitals. More than 600 acres of the campus, including most of its buildings, were listed on the National Register of Historic Places in 1984.