After a few years, however, he got the desire to run his own company again and Dexter Shoe Company was born. Harold bought an old woolen mill in Dexter, Maine in 1956 and started making shoes for the "make-up" market (Sears, JC Penney, Spiegel, Montgomery Ward & Co., etc.). Although Dexter was successful from the beginning, Harold soon tired of being controlled by a few large customers and decided to go into the "branded" business. He developed a line of shoes under the Dexter name, hired a sales force and began selling to independent shoe stores across the country.
Harold is often credited with the invention of the factory outlet store. Because factories make mistakes, not all shoes come out as first grade. The mistakes are called FDs (factory damaged). The practice in the industry was to sell these FDs to jobbers for about a dollar a pair. The jobbers would resell them for five times their cost. Harold thought that was a pretty good mark-up so in the 1960s he opened an outlet store at Dexter's Skowhegan factory and started selling his own FDs. Soon, the factories weren't making enough mistakes to supply the store so Harold decided to put in stale inventory (first grade shoes that weren't selling in the wholesale market). This worked so well that Dexter's log cabin style outlet stores started popping up on all the heavily traveled roads throughout New England. Other manufacturers caught on to the idea and as Dexter put up new stores, other manufacturers would open their outlets next door. By the 1990s the Dexter Factory Outlet chain had expanded to over 80 stores. About this time, Dexter also stopped building freestanding log cabins and began leasing stores in the new "Outlet Malls".
Dexter continued to grow rapidly throughout the 1970s and 1980's, and from time to time corporate suitors came calling to see if they could entice Dexter into a marriage. Many of these were national retail chains that promised rapid expansion, but would emphasize foreign production and likely, a departure from Dexter’s family style of running the business. Finally Harold decided to sell, to Berkshire Hathaway, which agreed not to interfere with the family's continued management of the business. On November 7, 1993, Dexter and its affiliates, Pan Am Shoe and Ocsap Ltd., were sold.
Harold founded Dexter Enterprises, Inc. in 1996. The company has served as an important management resource for all family members, with their investment, legal, and business interests. In 1997, Harold launched the construction and operation of the Belgrade Lakes Golf Course, which has been recognized as among the best public golf courses in the country. In 2002, Golf Digest recognized the course as the only 5-star public golf course in the Northeast.
In 2007, having lived with cancer for 17 years, Alfond donated $7 million to a cancer care center at MaineGeneral Medical Center in Augusta. The center is named the Harold Alfond Center for Cancer Care.