In the 1700s, the area now comprising southern Vermont and northern Massachusetts was subject to frequent Indian raids. To protect the growing population, Fort Dummer was built in 1724 on the site of the future town of Brattleboro. It served as both a scouting post and a trading center.

The security of the fort attracted settlers who cleared 200 acres surrounding Fort Dummer in 1752. A year later, this area was charted as Brattleboro by King George II. The town was named after its title owner, William Brattle, Jr., a colonel in the King's Militia, Harvard graduate, preacher, lawyer, doctor and legislator. Following his military duty, Brattle died in Nova Scotia in 1776 during the outbreak of the Revolutionary War. He never visited the town named after him.

Throughout the remaining years of the 18th century, Brattleboro's population continued to grow and flourish. A gristmill and sawmill were built on Whetstone Brook. A post office opened in 1784 at the Arms Tavern, the current site of the Retreat Farm. Because the town was on a stage coach route, the economy benefited from the trade of grain, lumber, turpentine, tallow and pork.

Industry and commerce thrived in Brattleboro during the 1800s. The Vermont Valley railroad ran directly through town, providing a vital link north. In the 1840s, Brattleboro developed a reputation as a resort town. Pure springs were discovered along the Whetstone Brook by Dr. Robert Wesselhoeft. The Brattleboro Hydropathic Establishment, more commonly known as the "water cure", opened in 1846. Wealthy patrons from the United States and abroad came to Brattleboro for treatments which included plunges in the cold, pure springs, long walks in the woods, healthful food, and no alcohol or tobacco. The water cure operated until 1871.

Not long after the establishment of the water cure spa, the Estey Organ Company was founded. It employed more than 500 people and marketed its reed organs as far away as New Zealand. Brattleboro truly became the organ capital of America. The prosperity of the Estey family also funded other enterprises in Brattleboro, including banks, and a sewing machine company.

Modern Brattleboro's economy is healthy and growing, primarily because the town has diversified its industrial and commercial base. Numerous businesses here provide stable employment. Brattleboro is a forward-looking town with a proud past.