Dave Leonard

Juliet: What brought you to Woodstock?

Dave Leonard: I was in Jackson Hole bartending during the day and dj’ing on the radio in the evenings. I fell in love, moved back east, lived in Pine Plains, and got married. I found DST (WDST Radio Woodstock 100.1) and I applied for a job and that next week I was hired.

Juliet: What year was that?

Dave: 1989. I was in Jackson for a few years, I thought I was a lifer in Jackson Hole. I met Leslie who became my wife, now my ex, who I have remained friends with and I just had dinner with her on Thursday.
I got here in the spring and I spent the summer getting acclimated, heard Jeanne Atwood on the radio, and then at the end of summer I called Richie Fusco, went in, and was hired to work seven days a week. I had my first air shift on Labor Day Monday, I drove 39 miles each way from Pine Plains and dj’d every weeknight following Betty MacDonald. I also dj’d on Saturday mornings with Nic Harcourt and I was the dj who replaced Classical music on Sundays. I had to handle a lot of angry calls. At the same time I was hired as an account executive for the Taconic Press (the local weekly newspaper in Dutchess County). That was my day job. So I quickly became immersed in the community working two jobs, starting my sales and on air radio career at the same time.

Juliet: What’s your first memory of Woodstock?

Dave: Getting lost on my way here (laughs). Also Woodstock Leathers, The Tinker Street Cafe, Gypsy Wolf, The Bear Cafe … and of course the radio station (then at 118 Tinker Street). It was kind of surreal driving into town and not knowing then that it wasn’t the actual “site”. It seemed charming, artistic and folksy. I loved Woodstock but I wasn’t drawn to it because of the festival or anything like that. That was before my time. I just liked that it had a cool radio station in town and that I didn’t have to go to New York City to make a living.

Juliet: Since you’ve been here, what has changed about Woodstock?

Dave: Ah, well it’s funny. I’ve seen this town from many perspectives; being married, being single, as a guy who stayed out late nights and went to shows, as a local dj, and now as business owner (JTD) and a single father. When I lived across the river I saw town from behind the scenes. Almost all of the local businesses would play the station in their stores and they’d hear me on the air, call in, and request songs. We’d talk and become friends but when I would walk through town and shop, no one would know who I was.

It feels very vibrant right now. It’s always had character and culture. I used to go to the Tinker Street Cafe and there was live music almost every night. I’ve seen it kind of dip down for a bit economically but now it feels alive again, there is so much going on. I am now seeing town as an entrepreneur and a parent. From all these different perspectives and as I grow older I ask myself, is it me or is Woodstock changing? Is no one going out late into the morning, or is it just me? I love having Woodstock as a place to raise my kids and getting to know so much of the community that I didn’t realize existed before. Initially I felt like a young outsider who came into town for work, and now at our weekly softball game I’m considered a local and an old timer. For the past 25 years I have immersed myself in a lot of the goings on in town. It’s always been a community which I’ve loved, one with artistic integrity filled with people just living and enjoying their lives.

Juliet: What is your favorite thing about being in Woodstock?

Dave: There is no judgement. Everyone gets to live the life they want to live, I get to experience total freedom, make a living, and I get to raise my kids in this magical place. There is such a diverse population and so much to learn from everyone that I come into contact with. I love being in a rural community that has an artistic sensibility and so much culture partly because of our proximity to the city. Whether dj’ing at a wedding or on the air, my work is all about music – and Woodstock being the music capital of the world lets me live the best of all worlds. I also love to travel, but no matter where I go I always think how much I love having Woodstock as my base and how much it is like living a vacation and how grateful I am that I get to be here.