In 1847, Middletown was New England's largest inland port, and it was in that year the company that would become Wilcox, Crittenden & Co., Inc. was established. According to the centennial history of the company, it was in Ben Butler's sail loft in Middletown that Eldridge Penfield first conceived of developing a metal grommet (later to be called the sail eyelet grommet) to replace the rope grommets that were currently being used by sailmakers.

In partnership with his uncle, Ira Penfield, Eldridge Penfield formed the firm of E. H. & I. K. Penfield. The business was opened in a small building at the rear of the property located at Main and William Street in Middletown, and was the first company in America to produce metal grommets. The first grommets were stamped out using hand presses which were operated by the partners and by William Walter Wilcox, whom they had hired.

For the next two years, Penfield tried to market the new grommets by utilizing traveling salesmen who brought and sold on consignment and kept most of the profits. After this unsuccessful period, Eldridge Penfield sold out his interest to Ira Penfield, and Wilcox invested his savings and became a partner in the new firm called Penfield & Wilcox.

By using more direct marketing techniques, Wilcox was able to overcome the opposition that developed on the part of journeymen sailmakers who feared that the use of the new grommet would reduce the need for their services. The company prospered and added other items to their inventory based on the needs of sailmakers. In 1857, Wilcox invented and patented a new and improved grommet made in three parts which was even more successful than the original device. He also invented a round-edged sail thimble which replaced the iron, sharp-edged thimble previously in use.

The partnership of Penfield & Wilcox was dissolved circa 1859, when Ira Penfield retired. Wilcox moved the business and took into partnership Joseph Hall, Jr. of Portland, CT and formed the firm of Wilcox & Hall, which continued until 1867 when Hall retired and sold his interest to Wilcox.

In 1869, Wilcox formed a partnership with three of the younger men of his organization, Albert R. Crittenden, E. Bound Chaffee, and Homer Churchill. Crittenden purchased a tenth interest in the business for $5,000, and name of the firm was changed to Wilcox, Crittenden & Company.

In the maritime world, steam was gradually replacing sail, and the company's 1870 catalog offered such varying products as shackles, thimbles, ring bolts, "Ereful whistles," engine-room signals, boat nails "of good Swede's steel heavily galvanized," and cotton hooks "New Orleans pattern." A new outlet for sailmakers was in manufacturing awnings and the company began stocking awning hardware as well. In 1883, Wilcox developed an improved brass grommet (which became known as the spur grommet), secured its approval as standard equipment by the British Admiralty, and eventually it was adopted by all the leading navies of the world. By the late 1880's, Wilcox, Crittenden & Company had become the largest manufacturers of marine hardware with the most diversified line in the United States.

The company survived a fire in 1907 which destroyed a large portion of the plant. They maintained during the World Wars and the Depression and by 1961, Wilcox, Crittenden & Co., Inc. was a division of North & Judd Manufacturing Co. By 1971 it was a Gulf + Western Precision Engineering Company, and by 1975, a division of Gulf + Western Manufacturing Company.