Oral History Interview with Shirley Cannon, Pine Castle Woman’s Club President Emeritus

I remember thinking that Pine Castle was very important to the community, but they didn’t know they were important. And I came up with a slogan for them, that would promote them: “The Heart of the Community Since 1940.” Excerpt from an Oral History Interview with Shirley Cannon, President Emeritus of the Pine Castle Woman’s Club, January 28, 2026.

Shirley Cannon is Pine Castle Woman’s Club President Emeritus, First Executive Director of the Pine Castle Center of the Arts, founder of the Pine Castle Historical Society and the designer of several published books.

LISTEN Part I of II:

Shirley Jane Cannon and I was born in Birmingham, Alabama.

Is that where you grew up?

No, when I was two my parents moved to St. Louis and I grew up in St. Louis, in a suburb of St. Louis.

What was life like? Did you enjoy school? Were you in Girl Scouts? What was your growing up like?

I would say I had a wonderful childhood. Mother and Daddy were both very generous people. And did everything they could for me. I was an only child. And I remember being very careful of myself because I knew they loved me so much and if I did something and killed myself by accident, they would be very hurt. So I remember as a young child being careful.

What was a typical Sunday like for you growing up?

Well, I went to the Methodist Church. Daddy was a Methodist. Mother was a Baptist. And I remember Mother never went to church because she said she had so much church when she was young, that she had enough to last her, her entire life. Daddy was a Methodist, so I became a Methodist. And I would go to church with him, not every Sunday, but occasionally. I always loved going to church with him.

Sunday School

And I remember that we had a wonderful head of the Sunday School, the Methodist Church Sunday School. And he and his wife were such good, sweet people that I always enjoyed going, mainly because of him.

Were you in clubs? Were you in Girl Scouts?

Oh, I was in the Girl Scouts. And I remember, I had a fabulous Girl Scout leader. And I remember she was very fat, obesely fat. But she was such a wonderful person, we just looked past that. I remember thinking she was just, almost perfect.

Five Blocks Away from School and Church

And I remember we lived within five blocks of the church. And so, I remember I would walk to Sunday School. I was close to the school and the church so I walked both places. I think I was five blocks away. And, my next door neighbor was Catholic and she didn’t go to church very often. So once and a while I remember she would go with me, and she always liked that.

So you had friends in the neighborhood?

Yes. My neighborhood was divided into city blocks. So at the corner was a nice family, their name was Herder and I used to, one of their daughters was I think a year older than me and I would go there and spend the night.

Orange Juice in the Morning

And, Mrs. Herder, would in the morning always bring us a glass of orange juice first thing in the morning. And I just thought that was such a nice thing to do. To be waked up in the morning with a glass of orange juice.

Hollyhocks

And the other thing I remember about Mrs. Herder, she was English, so she was very severe looking, very prim and proper. And she had hollyhocks. Do you know what hollyhocks are? So one whole side of her yard was a row of the most gorgeous hollyhocks you have ever seen. So that was one of my favorite things, when they were blooming was to go to her yard and look at her hollyhocks.

What a wonderful memory.

Yeah. I loved, in fact, I’ve done a couple of paintings of hollyhocks that turned out really, really nice.

What was your career path after school, after you finished your education?

Well, I always knew, I was always good in art. So I always knew that I was going to major in art in college. So I went to the Washington University in St. Louis which still has one of the best art departments in the country. So I went there and majored in Art. And I won the freshman scholarship, I remember that, for art.

We got married…

And then when I was a sophmore I fell in love. And my lover was going to medical school at Columbia Missouri… At some point we got married and moved to Columbia, Missouri where he was in medical school.

Medical Wives Club

And I remember, I was only 19 and I joined the Medical Wives Club. And most of the ladies were in their twenties and I thought they were very old. And they elected me President. And years later people would say to me, “Well, you know, why did they elect you President when they were older and you were very young?” And I said, “I think it is because I always sat in the front row.” And, I’ve been elected President of other organizations all my life. And always, I think it’s because I sit in the front row.

And they were fostering your leadership as well, right? And you went on to have many leadership roles throughout your life and to foster leadership in others.

Well, I guess, it did foster my leadership.

How did you happen to come to Orlando?

I was married and my husband was an MD. And he had a very good friend also an MD and we lived in Miami. I think they both went to the medical school in Miami. And so, they decided that they would like to open an office together. And so, I remember us talking about where they would open their office. And they decided they didn’t want to open it in Miami because Miami was too crowded. So they looked for a nice small town. And they decided on Orlando. And in those days, it was a very nice, very small town. and they liked it because it had a little culture. In Winter Park, there was a school, and I remember us thinking there’d be a little culture. And in those days, that’s about all there was in Orlando was Winter Park.

Rollins College was there?

That’s what we thought was the little culture, Rollins College.

How did you happen, did you join the Pine Castle Women’s Club when you came to this area or was it later?

You know, that’s a good question. One of the first people I met was Florence Fishback… and she heard that I was an artist and she loved the community and was always thinking of things to do to try to make it a better community. So she came up with the idea, of trying to get all of the businesses to put an awning out front and to plant some flowers in front of their place of business. And then she got me to do a painting of their business. She thought that would encourage them. So I did that. And, I think those paintings are still around somewhere. I have no idea where. But, you know, I put awnings and flowers out front. I remember Florence saying – it was her idea to plant flowers. I remember that. So anyway, right away they elected me President. I remember that.

And were you living in this part of town?

I lived up six blocks north of town in Edgewood. But, I was always interested in history and I knew that Edgewood was not a historic town, but Pine Castle was. And so when people, my friends from downtown Orlando would say, “Well, where do you live?” I always said, “I live in Pine Castle.” Although I really lived in Edgewood.

There was a prestige factor there with the history.

Well, no, it was not fancy. It was homey. Pine Castle was a homey place as opposed to Winter Park which was fancy.

The culture distinctions of the neighborhoods, right?

Yes.

…You served in the arts community providing a leadership role in Orlando.

In Pine Castle. I don’t think I was very involved in downtown Orlando.

Would you tell us about some of your experiences… you served as President of the Pine Castle Woman’s Club, right?

Yes, a couple of times. And my best friend was Florence Fishback and she had been President also a couple of times. And another good friend was Irene Day and she was President and, a wonderful lady.

“The Heart of the Community Since 1940”

And I remember thinking that Pine Castle was very important to the community, but they didn’t know they were important. And I came up with a slogan for them, that would promote them: “The Heart of the Community Since 1940.” That was the slogan.

I’ve heard that slogan.

That was my slogan. And it really was true. It was the leadership in the community. Pine Castle was, this is terrible, but in my head I called it poor pitiful Pine Castle because in many ways it was poor and pitiful. And then, later on I remember thinking… when I realized that Pine Castle wasn’t doing too great, and I wondered why because there were all these million dollar houses up and down this road. And I can’t remember if I asked someone why they didn’t come to the Woman’s Club… this person said, “When I get to Orange Avenue I turn right. I never turn left.” That was kind of how everybody was, they got to Orange Avenue and they turned right. No one turned left. So I thought that was terrible, you know.

You’ve been involved in a lot of activities over the years, you’ve named some very important friendships. The people that you named, were they people that you met here at the club. Is that how you met them?

You know, one of the first people I met was Florence Fishback… We both belonged to a sorority Kappa Kappa Gama. I don’t remember how I met her… Anyway, the first thing that Florence did was take me to the Women’s Club… Irene Day was one of the first people I met. She was a President a couple of times and Florience Fishback was a President a couple of times. Later on, I could name other movers and shakers at the Women’s Club. One is Gail Padgett, big time mover and shaker.

Ruth Barber Linton

This is a very important person: Ruth Barber Linton. She was one of the few people that was a native. Everybody else moved in, but she grew up here.

Did you meet her?

Yes. Ruth was just a precious person. She knew all of the history of the community. And so, I did this book: Pine Castle: A Walk Down Memory Lane by Ruth Barber Linton, Book Design by Shirley Cannon. These were two people that were very important in the community back in that day. They were friends of Ruth. She was a native. So she was one of the few people who was a native of the community. Because so many people were new and were moving in, but she had grown up here.

So a lot of the people that came to the Woman’s Club, they found community here in the Woman’s Club, a community network.

Yes.

And they found opportunities to become involved in some of the activities. So what would be some of the activities that you or members participated in?

We wanted to improve the community. And one of the first things we did was to plant oak trees on the west side of Orange Avenue from Pine Castle close to downtown. We planted a lot of little oak trees. And then, one of the next things we did, is we planted oak trees on the north side of Oakridge Road. So when you see some nice oak trees, we planted them. And, we built a nice gazebo… there was three acres of property… and my mother gave $10,000 dollars to help buy that property. And we built a gazebo and a lot of good things happened around the gazebo. And then, somehow or another, it ended up in the hands of a school…

I have done some interviews with people from this area, and they specifically remember the gazebo. That was something that people mentioned in the interviews, very happy memories of different community events where they would all go meet at the gazebo…

In it’s day, it was one of the most important things in the community…

I’ve heard about this gazebo as a recollection of a center of community life, a bringing together of people and very happy memories.

It really was.

Talking about some of the leadership and the contributions in the Pine Castle Woman’s Club, what would be some of the activities that you organized? Were they teas? I know you organized the Pine Castle Historical Society, some of the art programs.

One of the best things we did, we sponsored the, we called it the Four Arts Workshop. And that was for the summer. And I remember, my goal, was to get the best teachers in the community. And I’m talking about all of Orlando. So I found out who were the best art teachers and music teachers and drama teachers in the bigger community. And summer was a slow time for them and so they were happy to take part in our activity down in poor pitiful Pine Castle.

Four Arts Workshop

And I remember we had, we called it the Four Arts Workshop. And we taught music, painting, drama, drawing… My goal was to find the best teachers in Central Florida. And invite them to take part in our summer camp, arts camp. And they could teach whatever they wanted. In other words, the goal was not to get specific subjects taught, but to hire the best teachers…

Did you have a lot of students?

Oh, it was a famous camp. In fact, the head of the art department at Rollins College sent his child there. And he just thought it was fabulous. And he said, “Shirley, this is the best arts camp in Central Florida.You need to make it a residential camp.” And I said, “No, I can’t see how we could do that.” But that’s how much he thought about it. But he was the head of the art department at Rollins College and thought that we had a tiptop program… Well, it was because I hired the best teachers…

Harriett Lake

Harriett Lake was a wealthy woman and when she was young, she had lived in Pine Castle. Nobody knew that. Famous wealthy lady… So she had a soft spot in her heart for Pine Castle and at one point, she gave us ten thousand dollars. And I don’t remember if it was for a specific reason.

Was it for the kitchen remodel?

Oh, it was for the kitchen because I think for a while we called it Harriett’s Kitchen. Good for you.

You mentioned some of the students, because you mentioned the summer Four Arts Program. You’ve also had an ongoing association with the young people at the Russell Home, right? There’s an association between the Woman’s Club and the Russell Home?

Well, the Woman’s Club, their number one charity was the Russell Home. I remember we had a dance, for the Russell Home. And why I remember it distinctly is we invited them all to come to the Women’s Club for this dance. And I danced with a boy who was big and very athletic. And he would kick his legs up in the air, you know way high and I would try to do the same thing. I remember I hurt my legs. They hurt for a long time after that because I was trying to keep up with him…

LISTEN Part II

You’re known for your tea events and chili cookoffs, different events that you’ve had, garage sales things like that, that money would go to the Russell Home.

Yes. That was our main charity was the Russell Home.

…It’s Pine Castle Woman’s Club, but if I understand correctly it’s part of the General Federation of Women’s Clubs.

Yes. In the beginning we didn’t really know that. We were our own organization and then at some point we found out that we were part of a bigger organization… We found out something and we’re very proud of it. The yellow line that is in the middle of most highways now, was a project of the National Woman’s Clubs of which Pine Castle is a member.

That’s very interesting. Did you ever attend one of their meetings?

I think I did one time but I don’t remember anything about it.

We touched on your leadership. As someone who has had so many successful leadership positions, what do you think makes a good leader? How have you done it?

Working hard, number one. And having fun working hard.

You were a large part of the leadership behind forming the Pine Castle Historical Society. And through that you led to get books like Dateline Pine Castle by Dr. Weir published. How did you get the idea?

Yes. Well, I remember when I first moved to Orlando, one of the first people I met was Florence Fishback and Florence wanted to start an arts center. And I said, “But Florence, there is no art in Pine Castle.” There was no art in Pine Castle. I said, but, it’s a very historic place. There’s a lot of history. Why don’t we start – anyways I wanted us to have an organization that focused on history not art. Because we did have a lot of history and at that time, I didn’t know of any art in Pine Castle.

And that’s interesting because as we know you have a professional art background and you did have the successful art program here. And then later your dream comes to fulfillment because you lead to have the formation of the Pine Castle Historical Society that’s in existence now.

Right.

How did you do that?

How did we build the Woman’s Club?

How did you build the Woman’s Club and then how did you build a strong historical society like the Pine Castle Historical Society?

That came much later. Florence wanted to start an arts center and I remember saying to her, but Florence there’s no art in Pine Castle. How can we have an art center when we have no art? And so, we talked. And I said, “But, we have a lot of history. Why don’t we start a history festival.”

So that was the origin of Pioneer Days?

Yes. I said there’s a lot of history and we could have a lot of fun with that. But at the time there wasn’t any art.

Four Arts Workshop Summer Program

So at some point we had developed an organization and I remember, oh, it was the summer program: Four Arts Workshop. And we had a wonderful music teacher, who taught piano and singing. And, Herman, I think her name was Herman, she taught painting. And we had a lady who lived out in Belle Isle who taught piano. We taught drama.

Pied Piper Players

How did we do that? We started the Pied Piper Players. And for a while that was a really cute nice organization. Oh, I remember they put on plays. Betsy was in one of the plays (daughter) and my daughter, Mary Jane, starred in Red Shoes. It is a famous play. So we put on plays. Did we charge admission? If we did, it was minimum…

And the people who came to these programs, they were from this area?

Yes.

Did the club meet year around, or four times a year?

I think the Pine Castle Woman’s Club did not meet the three months in summer. So nine months of the year.

And then the other times of the year, you had ladies who came, you had different events organized that they would participate in, different activities like crafts. You had craft shows or art shows, teas or games?

At some point, we started having teas. I remember how we got started with the teas. One of our charities was The Russell Home. And the Russell Home had a tea room. And that gave us the idea of having tea parties because The Russell Home whoever organized it did a very good job. They had lovely teas. They had one room, so it wasn’t big, but it was done very, very well. So that’s how we got the idea of having a tea room.

And some of the activities and programs that you’ve mentioned continue to this day. So you have the Corner Rose Tea Room that people can schedule, they can call or go online and schedule. Pioneer Days is coming up next month in February. Pioneer Days is a big successful event that the public comes to. And then the Pine Castle Historical Society, that continues. And then the Pine Castle Woman’s Club also has community meetings, like the Pine Castle Historical Society will meet at the Wome’s Club for a meeting or a church event.

That was one of the moving forces for the Women’s Club was the fact that the community needed a place to meet. And so, when I first came, the Woman’s Club I would say was floundering. And I remember I had one of my grandson’s come and paint. And he painted the club inside and out. And I think the club was painted pink and I had my grandson paint it white inside and out. And at some point, we got the idea of having a garden.

Is that Flossie’s Garden where people can buy memorial bricks?

Same garden. Somehow we got the idea of putting bricks in the garden… we thought that would be a way to honor people would be by putting their name on a brick and they had to pay for it. And then that helped the club. It became a fundraising tool.

There have also been times that the Boy Scouts have come to help with different events like in the parking lot and things where they have done some community collaborations with the club. Troop 184.

Did they plant the hedge? And we planted some oak trees. And then the other thing, I mentioned that before, we planted oak trees all up on the north side of Oakridge Road and on the west side of Orange Avenue. So that was a big undertaking.

We only have so much time and there is so much that you’ve accomplished… You’ve done something that is quite creative, quite an accomplishment in terms of not only did you start the Pine Castle Historical Society, but you arranged, you collaborated, you got this important book published: The Dateline Pine Castle by Dr. Weir with the Will Wallace Harney archives. Can you tell us a little bit, did you just decide to call Dr. Weir? How did that come about?

Well, that’s a good question… He was a fabulous man. He was really one of the best people I ever knew, Dr. Weir. He had a wonderful wife. I remember that. He was just a great person.

He was a UCF History Professor, right?

Yes.

It was your idea to have him do the book, The Dateline Pine Castle, right?

Yes.

And then the Pine Castle Historical Society arranged to have it published?

I think I did.

I thought so.

Yes.

And it’s a hardbound, very nice, well done book.

Yes. I love to do books. I’ve done several. In fact, it’s one of the most favorite things that I’ve ever done is books. I did one for my family called: A Labor of Love…

Speaking of your family, I haven’t asked about that, but I understand that in addition to all this community activity and leadership and all the ways that you’ve been so generous to this area, you also are a mother, right?

Yes, six children and 14 grandchildren and two great grandchildren.

Oh my goodness. What an extraordinary life and legacy.

Yeah, I’ve had a full life.

And you’re still very much contributing in so many ways.

Am I?

Yes, because I read about it… We do appreciate your valuable time today very much.

I’m happy to get prodded to remember.

And it is the 86th year of the Pine Castle Woman’s Club. What do you see as the future of the club? Do you see the club continuing to be very much a part of the community, and making a contribution and sustaining the culture?

I do. And our President right now is a former school teacher and a black lady which I am so happy about. And she’s a wonderful leader, really good.

Veronica Bryant?

Yes. So I see that I would like to see the Woman’s Club continue to be a leader in this community. And I think with Veronica it will be. And I know we never had much participation of the rich ladies who lived down on Machette Road. And I have a vague recollection of trying to figure out why this was… there was a time when I was trying to involve those people more in the community of Pine Castle. I don’t think I was very successful in getting them to feel that, that was their community.

So you’re goal has always been to have a very diverse, inclusive community of all different demographics?

Yes.

Income, social, all different demographics. And in many ways you succeeded in that because there are many different community organizations who actually use this space.

Yeah. You know somewhere I did write what was the first, what had happened at the women’s club…. who used the club in the beginning. One was the Fire Department.

And they later gave a donation to the club.

Yes… They gave a lot of money, probably, $25,000.

That also shows the integrity of the club, that the local Fire Department brought forth their hard earned dollars to donate to this.

Yes. That was a point that I did make it some of the writing that I did was the fact that the Fire Department gave $25,000. And I remember talking to them and they said they had been saving up that money for years waiting for something they thought worthy of their money, and they gave it to the Women’s Club.

Many congratulations to you on all of your accomplishments, the ones that we’ve mentioned and the many that we have not mentioned and all the ways that you have contributed… I also remember in a conversation with you the contributions you’ve made have actually gone beyond this local area.

You have participated in some international activities. You went abroad to do some missionary work, right?

Oh, I went to Guatemala and that was a church trip…Methodist. I don’t think that had anything to do with the community.

But another way you have contributed in a humanitarian capacity.

Oh, oh yeah. And that was a wonderful, wonderful trip. And, it was very interesting. We went to the very north border of Guatemala. And there had been an earthquake. There had just been an earthquake and half of the road was down the mountain. And here we are in a great big bus on this little narrow road where half of it had slid down the mountain. And I was with, I took my granddaughter. And here, I’m thinking any minute we could slide down the mountain and be lost. And she never seemed nervous and I was about to jump out of my skin.

Making Friends

But we got to the top. And we met some natives. I can’t remember how we met them, but any way, she became very friendly with two of them. They were the same age. I mean they became really good friends.

Chimneys and Grates

It was an official trip sponsored by church, probably Methodist, that’s what I am. Anyway, what we were doing was bringing chimneys and grates to the natives. They still, this was modern times, they still sat on the ground and stirred their little fire while the smoke was, you know. I think it was a state project to bring chimneys and grates to these people so they could have more of a stove rather than a fire. So we did that. And there was some conflict going on. You know, major conflict.

You mean a political conflict.

Yes. So, here we go up to help the natives, up the mountain. And, about every hundred feet was a soldier standing there with his gun. It was a bad conflict. So we got up to the top and got into a little town. I remember looking on the map to see where it was that we were. And we were right on the border, the northern border of Guatemala.

American Woman’s Beautiful Home of Welcome

And there was, I think, one of the most beautiful buildings I have ever seen in my life there. And it was owned by an American woman, who obviously had money. It was like a hostel. Beautiful! One of the most charming buildings I have ever seen. I would love to go back just to see that building. Every room had its own fireplace. The garden, it was like rooms built around – what do you call it where you have the grass in the middle? (Hortus conclusus with partrerres.) Something ike that. It was really just one of the most charming, beautiful places I have ever seen. And here, we got there, on a ramshackled bus watching soldiers stand next to the road with their guns at the ready. And I’m bringing my grandaughter. So it was kind of an exciting trip. But really a fun trip.

My Grandddaughter’s Story

In the meantime, this granddaughter has an interesting story. She could not read. And she was in third grade and was still not reading. And somehow or another somebody figured out she had dyslexia. And she saw things, everything from the right to the left. So somebody did something to help her and she has become just a fabulous leader.

Her High School Leadership

So she met kids in high school and kind of became the leader of this little group, mainly boys, a few girls. These were all small town Florida kids, no money. And she has taken them all over the world. And how she does it is, she decides where she wants to go. She’s been to Japan. She’s been to China. She’s been to Europe. So she picks out where she wants to go and she makes arrangements. She’s says, do you want to go? Maybe ten of them will say yes.

World Travelers

So she finds a place where ten people can stay where ever it is their going. She makes the reservations. She tells the kids how much money they have to put in the pot. She takes the pot, she makes the arrangements. So when they get there, everything is taken care of. So she has taken those kids everywhere. So they’re just little small town Florida kids and they’re probably one of the most traveled bunch in the world because they have this one little girl that has dylesixia and can’t read. So she’s really cute and it’s a nice little story.

And it shows the continuation of the values of yuo and your family and how it continues through generations.

Yeah, I think so.

Thank you so very much for all the time you’ve spent with me today for the Library, for the Pine Castle Woman’s Club… The rich experiences that you have and the knowledge is wonderful to share with others. We appreciate your legacy of leadership and the significant contribution you have made in so many ways. And also, individual leadership with the people that you’ve interacted with and the ways that you’ve mentored people.

Well, thank you…

Interview: Shirley Cannon

Interviewer: Jane Tracy

Date: January 28, 2026

Place: Orlando Public Library

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