An ancestor of my particular Benedict line, Caleb⁴ (John³, John², Thomas¹) Benedict, was one of the 183 Proprietors of Canaan Parish in 1738 and was the first owner, builder and resident of the Benedict homestead on Brushy Ridge (which was also called "Benedict Hill"). It is likely that Caleb taught his two older sons, Caleb⁵ and James⁵, the techniques of making shoes by hand, because, together, these sons became the foundation of New Canaan's major industry. For five generations of sons, grandsons, great-grandsons, etc., starting in 1768, Benedict entrepreneurs created all the necessary steps of supply, materials preparation, factory development, assembly, finishing, wholesale distribution and retail sales required in order to build a dynasty in the shoe business. There were two generations of manufacturing at Brushy Ridge in which production, during and after the Revolution, reached 100,000 shoes per year. This was America's seminal cottage industry because various people around the town of New Canaan made the constituent parts of shoes. They then brought the piles of parts to Caleb's house where final assembly took place. Imagine! Assembly line production, 100 years before Henry Ford!

In the early 1800s, Benedict cousins opened competing shoe factories in downtown New Canaan. Caleb 's son, Caleb⁶, and grandson, Caleb⁷, were active shoemakers in Walton, New York; but Caleb⁷ 's son, Charles⁸, came back to New Canaan to join Benedict, Hall & Co. on Main Street. Other Benedict shoe enterprises in New Canaan were R.S. Benedict & Co., Benedict & Co., J. & J. Benedict & Co. and J. & T.W. Benedict, which continued into the 1900s. Ezra Benedict was a shoe jobber in New York City, and other Benedicts operated there both shoe manufacturing and retail businesses.

Mention was made that our Caleb⁴ was the root of both the lines of descendants that generated New Canaan's shoe industry. His son, our Caleb⁵, was active to some extent, but did not start his own manufactory, and while his other sons, Caleb⁶ and Ezra⁶, went on to produce generations of shoemakers, his son Aaron⁶, of our line, left New Canaan to homestead at Thompson, New York. Apparently, shoes held no particular fascination for him. Perhaps a bit short-sighted of him, for his other brothers and kin became wealthy and prominent citizens of New Canaan.

While New Canaan was experiencing its own Industrial Revolution, other things were starting to happen at the northern end of Fairfield County. The young town of Danbury had been founded in 1684 at the direction of Thomas¹ Benedict of Norwalk and settled by four of his children and their spouses. One of those original settlers was Thomas's youngest son, Daniel², who in 1675 had fought in "the direful swamp fight," otherwise known as King Philip's War, in which the local Peqout nation was essentially exterminated. For this "noble" service, Daniel and others were rewarded with parcels of land which were part of what was to become Danbury. A descendant of Daniel², Zadock⁵ Benedict (Matthew⁴, Daniel³, Daniel², Thomas¹), was born in 1737 in Danbury. Zadock started out as a farmer, but it is quite possible that he may have learned about how his cousins were building successful businesses with shoes down the highway in New Canaan. In any case, by 1780 he was motivated to start making hats to sell, and he seemed to follow principles developed by the Brushy Ridge Benedicts. He would have others bring materials (usually felt made of beaver pelts), and he would do the cutting and the blocking. With one journeyman and two apprentices, he was able to produce three hats a day, or one and half dozen per week. Out of this startup cottage industry grew Danbury's major economic resource. Danbury has been the home of several well-known hat manufacturers well into the 20th Century, names like Stetson Hats and Mallory Hats. And even though that industry has now died out there and been replaced by other types of manufacturing, Danbury is still called "Hat City." Interestingly, in the 1980s at the site of Zadock Benedict's old shop on Main Street, a restaurant opened with the name of "Zadock's;" it lasted a couple of years, but was replaced by another restaurant named "Benedict's." So the industries change, but the Benedict name goes on in the area.

Benedict-made New Canaan boots and Danbury tricorn hats (a Benedict invention) outfitted the better-dressed soldiers in the American Revolution. You might say that the Benedicts covered their tops and their bottoms.