Radical changes altered the face of commercial production in the 19th Century, touching areas as disparate as the highlands of Scotland and the valleys of Wilton. Driven by the steam engine and other technological innovations, entrepreneurs consolidated and expedited the production of agricultural and commercial goods, giving rise to the Industrial Revolution.

Wilton was no stranger to these changes. In 1860, shirt makers and shoemakers outnumbered farmers and day laborers, and mills and small factories dotted the landscape. The Gilbert and Bennett Wire Mill sprang to life in the quiet Georgetown area, and no fewer than three shirt factories existed in Wilton itself. (The “shirt factory” was basically a large room with a cutting board and some sewing machines.)

In North Wilton, Lewis Olmstead entered the shirt-making industry after losing his right hand in a railroad accident. His first contract with one Mr. McGrath of New York for two dozen calico shirts with puff bosoms nearly failed, but by 1860 he ran one of the largest shirt-making operations in town, employing more than 150 women from Wilton as seamstresses and a “Shirt Cutter” named Anthony Mucker and producing 4,000 shirts every year. From a capital investment of $5,000, he had annual revenue of over $10,000, and his successes were rivaled only by those of his competitor in Wilton Center, William A. Sturges.

After graduating from Wilton Academy in 1831 at the age of 14, Sturges traveled west with his two younger brothers to participate in the California Gold Rush, amassing a small fortune over the course of 10 years. In 1857, he used his accumulated capital to build a home on Ridgefield Road. Five years later he bought the old St. Matthew’s Church and moved it to Wilton Center, where he converted the first floor into a store and the second into a shirt factory. Like Olmstead, he employed more than 150 women, but unlike Olmstead, he never hired a “Shirt Cutter.” A testament to the profitability of both the factory and his short stint as postmaster for Wilton Center, Sturges died as one of the wealthiest men in Wilton.

Although just as successful as Olmstead and Sturges, the third shirt maker in Wilton ran a relatively small operation out of his father’s “Old Red Store.” Charles Cannon (of Cannondale fame) used cottage industry to produce his shirts, paying his 300 female employees on consignment for the vests, pants, coats, and shirts they sewed in their own homes. Between 1849 and 1857, he received lucrative contracts from five textile firms and sold surplus items in the “Old Red Store.” But despite his early successes, Cannon’s shirt-making enterprise dwindled after 1857, gradually losing customers until he ended it and closed the “Old Red Store” in 1860 to focus on his farm.

Like Cannon’s shirt factory, Wilton’s industry and its population declined after the Civil War. In 1860, 45 individuals listed their primary occupation as “shirt maker,” and hundreds more worked part-time for Olmstead, Sturges, or Cannon. The 1880 census, however, showed only 29 shirt makers, and by 1900 only 13 shirt makers still worked in Wilton. Likewise, the shoemaking industry grew scarce in Wilton: the town had a mere 30 shoemakers in 1880 compared to a high of 155 in 1850. Of the 1860 businesses in Wilton, only the Gilbert and Bennett Wire Mill in Georgetown survived past 1900.

No records of the later years of the Olmstead shirt factory have survived, but the factory likely closed with the death of Elbert Olmstead (Lewis Olmstead’s son-in-law) in 1886. The Sturges factory passed to William Sturges’s nephew Herbert Sturges, who converted it into a glove-making plant before aptly moving to Gloversville, N.Y. And Charles Cannon died in 1892, the last of the three great shirt-making entrepreneurs of Wilton. With his death, Wilton fell back into the agricultural slumber of the years before 1850.