In 1971, Dan Freeman opened up a leather shop in Middlebury. Tucked into a basement on 66 Main Street, Freeman stayed there for five years. Then one day in 1976, a student from Tulane walked through the front door and told him about a successful Jamaican shoemaker in New Orleans named Calvin Dayes. Freeman — who had long wanted to improve his craftsmanship — wrote Dayes a letter to see if he could work for him. After not hearing back, he hopped on a Greyhound bus bound 1500 miles to New Orleans. Three weeks later, he returned, closed his store and convinced his wife to move down south with their young son.
Today, the free-spirited leatherworker is back in Middlebury, running “Dan Freeman’s Leatherworks.” Surrounded by an abundance of tools and a 1925 Singer machine, he mostly makes belts and custom leather shoes known for their comfort and elegant simplicity. The process is meticulous, the leather comes from high-quality tanneries and the price tag is steep — upwards of $3,000 for the first pair.
“I have a few rich guys who like the idea of expensive handmade shoes,” Freeman explained. “But for a lot of people, it’s more about the comfort.”
Freeman’s journey up to this point was anything but orthodox. He grew up in suburban Philadelphia under strict parents. At 18, he went to Duke but soon realized writing essays wasn’t for him. At 21, the U.S. government drafted Freeman and he was shipped to Mannheim, Germany for two years.
“We used to joke about big red coming across the border,” Freeman said. “But from what I read now, we wouldn’t have been laughing so readily if we knew how serious it was."
After the army, he worked for a friend running a successful sandal shop in North Carolina. “We all have skills, and mine were in fine motor skills, hand-eye coordination, digital dexterity,” Freeman explained.
After a year, he and his future wife moved to her home state of Vermont. That’s when he opened up the shop on 66 Main Street, with his army friends studying down the road on the GI Bill. But Freeman wasn’t one to be pinned down for long.
“Son, go away and stop bothering me,” said Dayes, when Freeman showed up to his store in New Orleans.
Dayes had no time for people who weren’t willing to work as hard as he did. After coming to the U.S. in 1949 — stowed away on a British naval ship and with only $38 in his pocket — Dayes now owned his own business, house and had put his niece through Tulane University.
“I had to hang around the shop for three weeks and finally convinced him I was serious,” Freeman explained. “I was willing to sacrifice. I was willing to work for him for no pay.”
During these years, Freeman’s wife supported the three of them through her work as a teacher. Freeman contributed by taking care of their son in the mornings, before heading over to Dayes’ shop, where he would work until 7 or 8 p.m. The lifestyle wasn’t easy, but it allowed Freeman to learn many of the advanced techniques he needed to start his own shop. The two shoemakers soon developed a close bond.
“Calvin used to tell me he couldn’t die yet because I didn’t know how to make shoes,” Freeman said.
The decades of Greyhound buses and spontaneous decisions eventually faded to history; Freeman has now run his own shop in Middlebury for the past 41 years. He has watched generations of college students stop by to buy a belt and sold countless shoes to customers around the country. And behind the counter today, his grandson Max Freeman is starting to learn the trade.
“I’ve always liked doing stuff hands-on, tactile, putting stuff together,” Max explained.
Freeman represents the smoldering embers of a burning industry. He has outlasted many American shoemakers, who have been unable to compete with goods from overseas. He has survived a shrinking number of tanneries in the U.S., which have gone from hundreds in the 1980s to only a few dozen today. And at 78 years old, he continues to run the store five days a week.
Even his old friend Dayes was proud of where he ended up. When Freeman went back to see the shoemaker at his shop in 2012, Dayes told him: “Daniel, I think if you keep at it, you’re gonna get it."
Theo Maniatis ’28.5 (he/him) is a managing editor.
Theo has lived in the Sports section for all of his short newspaper career. He majors in Political Science with a minor in Spanish — and plans to study abroad in Argentina this Spring.
Outside the newsroom, Theo rows crew, plays guitar, and hangs out with friends.
