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The General John Stark Memorial Bridge is a bridge that crosses the Connecticut River between Brattleboro, Vermont, and Hinsdale, New Hampshire, in the United States. The bridge, which connects Vermont Route 119 and New Hampshire Route 119, replaces the Anna Hunt Marsh Bridge and the Charles Dana Bridge which formerly connected these routes. The Dana and Marsh bridges will become bicycling and pedestrian paths. The bridge opened for traffic on Thursday, December 5, 2024.

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.

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 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.

The Arthur D. and Emma J. Wyatt House is a historic house at 125 Putney Road (United States Route 5) in Brattleboro, Vermont. Built in 1894, it is one of the state's finest examples of a mature Shingle style residence. It was listed on the National Register of Historic Places in 2005.

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 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.

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.

Prospect Hill Cemetery is a cemetery in Brattleboro, Vermont. Founded in 1796, it was originally known as the Village Burying Ground, and then Old Village Burying Ground. Additional parcels land was acquired over time, up to 1869.The cemetery includes a number of notable figures from the history of the town. Included in the graves at the site, are those of 19 union soldiers who died at the military hospital in the town during the Civil War.

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.

WVEW-LP (107.7 FM) is a radio station licensed to Brattleboro, Vermont. The license to operate the station is held by Vermont Earth Works. The broadcast radius is from 3 to 5 miles (4.8 to 8.0 km). There are 56 volunteers on the staff.

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.