The town has been important to the history of Vermont, acting as a gateway for trade on both the Connecticut River and subsequent road and train infrastructure.

The location was called Wantastegok or "Wantastiquet" by the indigenous Sokoki band of Abenaki that resided in the area before settlement by Europeans.

Although the area was originally part of the Equivalent Lands, the township became one of the New Hampshire grants, and was chartered (founded) as such on December 26, 1753, by Governor Benning Wentworth.

[12] In 1834, the Brattleboro Retreat, then called the Vermont Asylum for the Insane,[13] was established through a generous bequest by Anna Marsh of Hinsdale, New Hampshire.

The company's main factory was located southwest of downtown Brattleboro, on the south side of Whetstone Brook between Birge and Organ Streets.

The entire surviving complex was listed on the National Register of Historic Places in 1980, both for its architecture, and for having been a major economic force in Brattleboro for many years.

In 1871, Thomas P. James, "The Spirit Pen of Dickens", a printer by trade, moved to Brattleboro, where he took a job at The Vermont Farmer and Record.

The book was printed by the same company that owned the Springfield Union, which was the paper that published the first news about James' claims, as well as excerpts from the new chapters of the novel.

Newspaper editors from papers around New England who had employed James denounced the entire affair as a well-planned advertising hoax.

He also wrote about local life in the early 1890s: heavy snowfalls, ox-teams drawing sledges, and people in the small towns beset with what he called a "terrifying intimacy" about each other's lives.

He recorded the death of men who had left, going to seek their fortunes in the cities or out west, and the consequent loneliness and depression in the lives of local women; the long length of the workday for farmers, even in winter, often for lack of help; and the abandonment of farms.

Summers are warm to hot and generally humid, with abundant sunshine and heavy showers and thunderstorms associated with passing cold fronts.

The majority of jobs based in Brattleboro are in the Health Care and Social Assistance sector, followed by Manufacturing, Government, and Retail Trade.

[31] C&S Wholesale Grocers, the northeast's largest regional food distributor, made its headquarters here until 2005, when they moved their administrative offices to Keene, New Hampshire; however, because of close proximity to Interstate 91, C&S still operates a large shipping and warehouse facility in Brattleboro near I-91's Exit 3.

The southeast quarter of the town, near to and abutting the riverbank, is where its population has historically been the densest, and is composed largely of one- or two-family houses, with apartment buildings such as "triple deckers" interspersed among them.

The town's high school and the Regional Career Center are also located in this section, as is Fort Dummer State Park, which is named after the first European settlers' 1724 stockade.

The original Fort's site, however, was flooded in the early 20th century by a flood-control and hydro-electric dam built just downstream in Vernon, Vermont.

An historical marker is located near the Fort's now-underwater site, on the west bank of the Connecticut River on Vernon Road (VT Route 142), at the corner of Cotton Mill Hill.

It is mostly lower-density residential in character, and features the state's largest mobile home park and several planned housing developments and subdivisions.

Away from the Route 9 conduit, other parts of western Brattleboro and some areas north of the West River have a decidedly rural character, with dirt roads, sparse housing, wooded Green Mountains foothills, and the last few farms left in the town following the 1970s' decline of the dairy industry.

The section of Brattleboro north of the West River, formerly farmland, was mostly subdivided and developed during the 1960s and 1970s following the construction of Interstate 91, which runs north-south through the town.

[52][53] The town operates and maintains the Gibson-Aiken Center, a large recreation and community activities facility, located downtown on Main Street,[66] along with a number of parks and outdoor recreation centers, including Living Memorial Park, whose features include an outdoor swimming pool and a municipal skiing facility.

There are bicycle lanes on Putney Road in the northern portion of town, on Guilford Street near Living Memorial Park, and on a short segment of Western Avenue in West Brattleboro.

[67] Brattleboro sees a substantial seasonal influx of recreational skiers and snowboarders, many of them bound for the resorts at nearby Mount Snow and Stratton, but it is also a winter sports destination in and of itself.

The town played an important role in the development and popularization of the skiing industry as a winter sport, with pioneering Brattleboro native and Dartmouth College alumnus Fred Harris,[68] founder of the Dartmouth Outing Club (1909–1910),[69] also establishing the Brattleboro Outing Club (in 1922),[70] contributing to the first North American use of motor-driven ski lifts, and building the Harris Hill olympic-scale ski jumping facility,[71] the site of international competitions every February that still attract daring ski-jumping athletes from all over the world.

At the state level in Montpelier: Brattleboro has a diverse mix of public and private primary, secondary and post-secondary schools and career centers.

[77] Its students and faculty hail from all regions of the globe, giving Brattleboro a decidedly eclectic and international flair, and its notable alumni include native Vermonter and 1997 Nobel Peace Prize laureate Jody Williams.

Brattleboro is not reached by terrestrial broadcast television due to the surrounding mountains, in addition to being just far enough away from major cities like Boston, Springfield, and Albany.

It meets I-91 at a partial cloverleaf interchange (from where it is Exit 2 from the Interstate), then as it advances eastward into downtown, it overlaps U.S. Route 5 at the intersection of Main and High Streets.

From this point, it runs for about 12 miles on a very gently graded roadbed along the West River's southern bank, affording a stunning vista and connecting Brattleboro with picturesque New England towns and recreational areas elsewhere in Windham County and Vermont.