Did You Know? - “If the Shoe Fits”

The VF Archive is full of fascinating first-person accounts of everyday life in Vermont and New England–past and present. In this feature, we'll share these stories with you.  

Since 2022 marks the 30th anniversary of the Vermont Traditional Arts Apprenticeship Program, VTAAP, we’re going to spend our first installments of Did You Know? looking at the lives and experiences of VTAAP participants over the years. We begin with master shoemaker Dan Freeman of Middlebury and apprentice Anne Callahan who worked together beginning in 2004. Freeman’s shop, Dan Freeman’s Leatherwork, has been a Middlebury staple for decades.

As a part of VTAAP, VFC fieldworkers conduct site visits and interview apprenticeship pairs. The excerpts below are taken from a site visit conducted on June 23, 2005 by the late Greg Sharrow.

  • Master Artist: Daniel Freeman, Cordwainer (Handmade Shoemaking) (interviewed June 23, 2005)

  • Apprentice: Anne Callahan

Daniel Freeman began his professional life as a leatherworker more than 50 years ago. In the mid 70s, after working for several years, Dan wanted to expand his skills and master the creation of more complex items: shoes and boots.  To do so, he spent two months apprenticed to a third-generation shoemaker in New Orleans:

Dan Freeman: I worked in a sandal shop in 1970 for a year where we made simple basic leather goods and I moved up to Vermont and ran a shop here for five years doing so. But people's tastes started to change as the seventies went on, and the taste for handmade-looking articles went down as the price of leather went up and the business changed. And I was always fascinated by the most complicated type of leatherwork, which was making boots and shoes...And by chance in 1976, while talking to a summer school student from Tulane who was up here at Middlebury who said, "Well, I know a shoemaker in New Orleans." ...I finally hooked up with him and after a great deal of discussion, moved to New Orleans and we agreed that I could work for him, for no pay, for as long as I wanted and it was definitely not a classroom situation, where he sat down and instructed me. It was me working for him in his shop and as the months went by, gradually I was permitted to do things. I stayed there two years and made a number of pairs of shoes. And the shoemaker and I stay in touch. He says he can't die yet because I still don't know how to make shoes. But after two years, I felt like I had gotten about as much as I could get out of him and he had given me about as much as he could, at least at that time, so I moved up here and I've been trying to learn how to do it from other sources and I've been practicing ever since.

In his interview, Dan talks in detail about the process of creating a custom-made shoe, as well as what draws him to the craft: 

Dan Freeman: I'm just fascinated by the prospect of visualizing someone's foot and visualizing a shoe and then making a shoe that fits that foot. It's the actual execution of the process that interests me. The actual making something that -- where you can test the result. They put it on, it's going to wrinkle, it’s going to fit, it’s going to hurt…whatever. But, you’re going to see the results. And people come in here with an idea of what they want their shoes to look like or what they want their shoes to do and if I can come up with something that does that I feel like I've accomplished a lot. That's what I like to do, is make shoes happen for people.

In 2004 Dan agreed to work with apprentice Anne Callahan through VTAAP.  In the interview Anne talks about the impact of their year working together: 

Anne Callahan: I'm starting to get an idea of everything that I don't know, which is a beautiful place to—you know, that's where I've come at this point. That’s very exciting —to see the infinite expanse of what I could learn about this craft...what this craft is. You know, what it takes to understand it.

One of the greatest things...I've learned kind of how to learn a craft...and the other…which is even more universally relevant, you know, less relevant to shoemaking, is how to learn from a person… which is the apprenticeship—the whole idea. You know, the delicacy of like when to ask questions, how much to ask and how much to just try and do. You know, how many mistakes you let yourself make and how much to watch. There are so many ways to learn.


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