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Brooks House, also known as the Hotel Brooks, is an historic building located at the corner of Main Street and High Street in downtown Brattleboro, Vermont. It was built in 1871 and designed by the architectural firm of E. Boyden & Son of Worcester, Massachusetts in the provincial Second Empire style for George Brooks, to replace a previous hotel on the site which had burned down. When it was completed, the luxury hotel had 80 rooms which were lavishly furnished. It was added to the National Register of Historic Places in 1980.

The Brattleboro Free Folk Festival is an American annual music festival which takes place in Brattleboro, Vermont. The festival began in 2003 and is considered part of the New Weird America music movement.

The Latchis Hotel and Theatre (orig. the Latchis Memorial Building) is an art deco building in Brattleboro, Vermont first built in 1938. The building is one of only two extant Art Deco buildings in Vermont. The building is run by the Brattleboro Arts Initiative, a local non-profit.The building was constructred as a memorial to Demetrius P. Latchis, a Greek immigrant who became an important businessman in Brattleboro, by his sons. Latchis had built a business which ran fourteen theatres throughout New England. The interior include murals and other artwork with Greek mythology, which was created by Hungarian muralist Louis Jambor. The building also includes terrazzo flooring. The building was designed so that it could include a hotel, theatre, ballroom, restaurant, bar, and other business spaces. The architect for the building was S. Wesley Haynes.Though a successful business through the 60s, the business slumped in the 70s. In 1985, two children of the original brothers revitalized the hotel. They sold the hotel in 2003 to a local non-profit, the Brattleboro Arts Initiative, created for maintaining the building, bought the hotel for 1.3 million dollars. The money included both local and federal grants. The building suffered considerable damage in 2011, during Hurricane Irene, but was reopened later that year. The building was further restored in 2013, after a half-million dollar fundraising campaign. Since the covid crisis they've introduced private movie rentals and still play big name films. In addition, they rent the smaller theaters out for video game playing. An entire family can play MarioKart on the big screen.

The Canal Street Schoolhouse is a historic school building on Canal Street in Brattleboro, Vermont. Built in 1892 out of locally quarried stone, it is a fine local example of Colonial Revival architecture. It was listed on the National Register of Historic Places in 1977.

Whetstone Brook is a tributary of the Connecticut River that runs through the heart of Brattleboro, Vermont, in the United States. It flows into the Connecticut at an elevation of 250 feet (76 m) above sea level. The headwater for the brook is at Hidden Lake, which is 1,500 feet (460 m) above sea level in the town of Marlboro. Of the 28-square-mile (73 km2) watershed, over two thirds is contained within Brattleboro, while another 30 percent is in Marlboro. The remaining 2% is within the town of Dummerston. The brook is crossed by Creamery Covered Bridge in West Brattleboro, which was built in 1879.

Brooks Memorial Library is a public library in the municipality of Brattleboro, Vermont. The library was founded in 1887. The current head librarian is Starr LaTronica who joined the library in December 2015. The library is part of the Catamount Library Network, which provides a unified library system for over a dozen Vermont libraries.

The Brattleboro Museum and Art Center (BMAC), a non-collecting museum, was founded in 1972 and is located in the former Central Vermont & Boston & Maine Union Station building in downtown Brattleboro, Vermont. New exhibits by regional and international artists are shown each season. The aim of BMAC is to present art and ideas in ways that inspire, educate, and engage people of all ages. Some of BMAC's notable exhibiting artists have included Jennifer Bartlett, Chuck Close, Janet Fish, Emily Mason, Wolf Kahn, Chris Van Allsburg and Andy Warhol. The BMAC's space also serves as community center.

Union Station (also called Brattleboro station) is an Amtrak intercity rail station located in downtown Brattleboro, Vermont, United States. It is served by the one daily round trip of the Vermonter service. Most of the 1915-built station is occupied by the 1972-opened Brattleboro Museum and Art Center, while Amtrak uses a waiting room on the lower floor. The building was added to the National Register of Historic Places in 1974.

The Canal Street–Clark Street Neighborhood Historic District encompasses a compact 19th-century working-class neighborhood of Brattleboro, Vermont. Most of its buildings are modest vernacular wood-frame buildings, erected between 1830 and 1935; there are a few apartment blocks, and one church. The district was listed on the National Register of Historic Places in 1993.

The Deacon John Holbrook House is a historic building at 80 Linden Street in Brattleboro, Vermont. Built in 1825 for prominent local businessman John Holbrook, it is a high-quality example of Federal period architecture. It was listed on the National Register of Historic Places in 1982. It now houses professional offices.

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.

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.