John Holbrook - How The River Built Brattleboro Village

Frugality, thrift and free enterprise were some of the watchwords that marked the beginning years of the United States.  Locally, John Holbrook personified these traits and was instrumental in the early development of Brattleboro’s economy.

Holbrook was born in Weymouth, Massachusetts In 1761, a town a little south of Boston.  His family was loyal to Great Britain.  During his teen years British officers stationed near Dorchester Heights taught young Holbrook how to survey land.  At the end of the American Revolution John Holbrook moved to newly settled Newfane, Vermont to work for Luke Knowlton. 

Knowlton was one of the first settlers of Newfane and was a local government official.  He had Holbrook survey much of the town.  When Holbrook was twenty five he married Knowlton’s daughter, Sarah.  Holbrook opened a small general store on Newfane Hill.  He took locally grown produce and hand-made goods on pack horses along the West River to Brattleboro.  From there he followed another trail to Greenfield, Massachusetts where he exchanged his items for dry goods and groceries.  He would pack these items back to Newfane and sell them in his store.

In 1794 John Holbrook moved his family to Brattleboro.  He purchased a mill and general store where the Whetstone Brook and the Connecticut River meet.  Holbrook entered into partnership with two wholesalers; one from Harford, Conn. and the other from New York City.  The wholesalers provided stock for the store while Holbrook operated the Brattleboro business.

Meanwhile, during the 1790’s the upper Connecticut River was opened as a significant trade route.  This lowered shipping expenses and increased the type of goods that could be shipped from one place to another. This meant goods could travel by flatboat back and forth from Brattleboro to Hartford and could then be transferred to larger ships that could sail anywhere in the world.  In 1795 the South Hadley Canal was completed and in 1798 a canal at Turner’s Falls was also finished.  This meant goods could travel by flatboat back and forth from Brattleboro to Hartford and could then be transferred to larger ships that could sail anywhere in the world.

In 1797 John Holbrook bought out his two business partners and went into the flatboat business.  He owned the first and largest flatboats that carried goods to and from Hartford. Holbrook expanded the building that housed his family residence and store to include a warehouse, (this building would later become the American House).  Holbrook became a wholesaler for the West River and upper Connecticut River Valley.  Records indicate he entered into partnerships with general store owners in Wardsboro, Townshend, Dummerston, Newfane and Chesterfield.

John Holbrook was not just a major flatboat owner and wholesaler of goods for other stores.  He continued to operate his general store at the bottom of Main Street and also owned a feedlot and slaughterhouse on the island between Brattleboro and Hinsdale.  He was also a partner in a local hide tanning business and director of the toll bridge across the Connecticut River island that connected Brattleboro to Hinsdale.  The bridge connected the turnpike systems leading to Boston and Albany.  This meant he would profit from the growing east-west land trade as well.  

At this time there was no bank in Brattleboro.  Much of the trade between people and businesses was done on the barter system.  As Holbrook’s businesses grew he became one of the first to bring bank notes to the area and introduce them as a means of trade.  Businessmen with little capital turned to Holbrook for financial resources and partnerships.  Many businesses, like the tannery, manufacturers and general stores in nearby towns, were financed by Holbrook and operated by others.

Holbrook did not just ship goods from Hartford to Brattleboro.  He also entered into many contracts with local farmers and businesses to procure goods to ship as far south as the West Indies.  His partnerships with various wholesalers in the Hartford area allowed him to participate in trade up and down the Atlantic seaboard and into the Caribbean.

In 1798 he began selling goods in his Brattleboro store from as far away as the West Indies.  His flatboat, “the Dispatch”, arrived in the spring with brandy, rum, sugar, salt, brown sugar, molasses, tobacco, rice, pepper, port wine, cotton and raisins. These were products from European slave colonies in the West Indies and southern slave plantations in the United States.   In return, Holbrook shipped cheese, butter, flax, wheat, rye, beans, leather, flour, and corn to Hartford. 

 Holbrook also salted meat from his slaughterhouse, loaded it into barrels and shipped the barrels to the West Indies.  The slave islands were so focused on production of the most profitable crops like sugar, salt, cotton and tobacco that they did not grow food for the people they had forced into slavery.  Instead, the slave islands imported food from New England.  

John Holbrook imported goods that could not be efficiently produced in New England and exported produce and salted meats to slave plantations in the southern United States and slave islands in the West Indies.  His strategy was to control as much of the supply chain as possible, meet market demands and provide items of a consistent quality. 

As the years went on, Holbrook was the most successful entrepreneur in the area. He had his hand in many regional businesses.  International tensions between the United States, Great Britain and France brought about a trade embargo in 1807.  The embargo cut into Holbrook’s trade with the slave islands and his profits suffered.  

Always looking for an opportunity, Holbrook sold many of his local business interests in 1810 and moved to Warehouse Point in Hartford, Connecticut.  He planned to become more involved in wholesaling, investments and regional banking.  

An examination of local newspapers show that stores not owned by Holbrook also sold slave produced goods in the area.  However, it seems that Holbrook was the most successful at this long distance trade.  While slavery in Vermont was illegal, the profits gained from selling goods from the slave islands in the West Indies and southern slave state plantations fueled investment in other local businesses and helped create the early industry and manufacturing concerns of Brattleboro.  All of this happened before he became involved in the book publishing business.  He expected Fessenden to be his local representative in Brattleboro.  When Fessenden died Holbrook came back to look after his local investments and expand the printing and publishing business.

Holbrook was the first, and most successful, local trader to use the Connecticut River for commerce and trade.  He made large profits and plowed them into the local economy.  Brattleboro’s publishing and printing business was financed through the success of Holbrook’s trade with the slave islands.

Holbrook accumulated so much wealth that he became the principal financier of other entrepreneurs, including William Fessenden (who married his daughter). Holbrook had already purchased the rights to publish Webster’s Spelling Book and, in 1815, when Fessenden died and Brattleboro’s paper mill burned down, Holbrook rebuilt the mill and continued Fessenden’s work of printing and publishing. 

Holbrook also hired machinists who took innovative approaches to the technical tasks of paper-making, printing and publishing.  He greatly expanded the enterprise by taking a gamble on the production and sale of high-quality, handsomely bound Bibles, printed on the best paper. The venture was a phenomenal success, and the “Holbrook Bible” brought even more wealth to Brattleboro. By the 1820s, publishing houses in the big cities were having some of their books printed in Brattleboro. By 1836, Holbrook’s firm did $500,000 worth of business in printing, bookbinding, and papermaking–nearly $12 million in today’s currency.


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