Catskills Conversations: Heather Rolland

© J.N. Urbanski

© J.N. Urbanski

Jenny: How long have you lived in the Catskills?

Heather: I moved to the Catskills in 2007, so I’ve been here going on eight years.

Where did were you living before?

I was living in Dutchess County in Dover Plains and I had been there 17 years. I grew up in Nyack. I’ve actually never lived anywhere more urban than Nyack. It’s been a slow and steady march northward.

What started that slow march?

When I was in High School. I had a buddy who – and this is a crazy story – we both turned sixteen, got our driver’s licenses. She quit high school and moved all by herself as a sixteen year old to Woodstock.


I kid you not. Her mom was an artist and her dad was a musician. Her family had a place and they rented her their converted barn. She and I would come up on the weekends during the school year, but they allowed her to rent this place. As a mom now to me it’s unbelievable, but at the time we could go do something like live alone in the middle of the woods in 1982! She lied about her age, got a job and made a life up here.

What happened to her?

Actually, we lost touch. She did complete her education. She went to SUNY Ulster and got an undergraduate degree and ultimately became a doctor. But that was my introduction to the Catskills. I have deep Catskills roots because my grandparents came up here in the 1920s. I have a beautiful box full of old photos of grandma and grandpa.

I would love to see those.

We’ll have to make a date. That was back even pre-Borscht Belt. They would come up from Brooklyn and summer in the Catskills. It was what you did back then. So starting in the 1980s, I was spending time here and hiking here and sort of beginning that trek from a place like Nyack, which was obviously much more connected to New York City, to be in the Catskills.

When I was looking into college I thought I was going to go to Portland, Oregon or Santa Cruz, California, but my mom said: no you’re not. You’re going to live at home and commute. So I went to SUNY Purchase. That was the beginning of my move north and finding places to live. I lived for a while in Peekskill and from Peekskill I moved to Millbrook New York and then Dover Plains. I raised my child when I was living in Dover.

So once you had got to Woodstock and were hanging out with your friend, did you think, oh well, I’m a country bumpkin at heart and I’ve got to be here, or was it more gradual?

Nyack in the seventies was pretty country-ish and where I was living was right at the base of Hook Mountain. My house was a tenth of a mile from the trailhead and my life was all about running around in the woods with my dog, because that was my chore growing up. I had to look after the dog. So it was a natural extension, to come up here to the Catskills and be like, oh my goodness, there’s so much more woods. If anything it was more home than home.


So as much as I could, starting at fifteen, being able to come here was a very natural fit. It was also very rural where I lived in Dover Plains. My passion has always been nature and wildlife and hiking. So I did a ton of hiking when I lived in Dover Plains because the Appalachian Trail goes through that area. By the time I was ready to move to the Catskills, I had already thoroughly smoked the hiking opportunities of the mid-Hudson, Hudson Highlands and surrounding area.

Excellent. What do you do for work?

I do three different things, all of which are cobbled together in different combinations, to try to make money. One thing I’ve been doing since before I moved to the Catskills is writing. I’ve written three novels and I’ve worked for several years professionally as a ghostwriter. That was a really fun wonderful experience of extreme, self-directed pressure. Constant deadlines and constantly producing material. I was only a fair to middlng writer prior to that, but a couple of years of constantly turning in high-quality, publishable material week after week… It was an excellent education in getting it tight.

I still get gigs here and there and am currently working very hard at self-promotion. I entered a short story contest and I’m currently sitting in second place. It’s an odd contest in that you win by the number of downloads. It’s not really judging your writing ability. It’s judging your ability to network and promote.

Right. That’s probably why they conduct those competitions. So it spreads the word of the website.

Exactly. They are paying out a first prize of $15,000. That’s a sizeable prize for a short story contest, but if you think about what it would cost for them to get this level of airplay in terms of advertising, it’s probably a bargain for them. The story is called Queen of the Catskills and it’s a re-telling of Hamlet set in an Arkville trailer park.

No way. I can’t wait to read that.

If you download my story, that gives me a vote and you will get the story. I will warn you this story is full of f-bombs. I am the “f-bomb Friday” lady, after all. I feel like writing fiction is a real luxury. I love it. I have so much fun. I really had a hoot writing this story, but much of the time I have to write non-fiction, whether it’s for my work or some other cause. I also have an article in the Catskills Mountain Guide in the May issue. It’s the backstory of the Mica Movie about a dog who climbs the Catskill 35 and fleshing out the story of how that happened.

I’d love to read that too.

I actually haven’t seen the magazine yet. I have to go and pick up the magazine.

I still like reading physical magazines. I don’t know how many of us actually like that. Do you know how many people just don’t read physical magazines anymore? Is that a large percentage of the readership?

You know, I think that it really varies. If people are in their regular, connected, wired lives, it’s going to be a lot less compelling. But if you’re in the Catskills somewhere where you can’t get a signal, yeah, there’s a lot more reading of physical things.

So what about your novels what are they like?

My first book was reviewed as a “local mystery with a garage band feel” which I thought was awesome. I thought that was the highest praise because it was bloody awful, frankly. [Laughs] I wrote it partly as an exercise because my daughter was quite young. We were doing a ton of reading together every night: classic young adult novels, a lot of coming of age stuff. As we read and read and read, we discovered that in order to set up a heroic, young character, you kill off one or both parents. You kill off their critical mentors and they find their way on their own. After a certain number of books with dead parents, we thought, you know, we’ve got to be able to write a decent story without killing anybody.

How about very distant parents?

Right, right. I mean it’s sort of variations on a theme. We wanted to maybe have everybody present. The exercise was about saying to my young daughter at that moment in her life: nothing is outside of what you can do if you put your mind to it. If we want to write, we can write; if you want to paint, you can paint and if you want to be a doctor, study science and math. It’s possible. There’s no reason why we can’t be creators, we don’t only have to be consumers. So we both came up with characters and at dinnertime, we would sit around the table and talk about what should happen in a story. What’s the central conflict? What’s a narrative arc? How do we do this? How do we create and resolve tension? They were great conversations to have with a 9 year-old.

Ah, sweet.

So we did it. We wrote a story and it was rough around the edges. It was a mystery and nobody died. My second novel was a bit of a sequel. It’s a hiking novel set in the Catskills in Delaware County and it’s a celebration of this place. It’ll make you laugh and cry. On the back cover it says, “betrayal, lust and a whole lot of hiking”. The characters essential take their angst with them up a mountain.

Did you have a book contract/deal for your novels?

No, I self-published.

It’s not that tough is it? I know people who have done it.

It’s extremely easy actually to do an e-book, but the issue is self-promotion. To get the word out and have people read your stuff, that’s the challenging part.

Right. So that’s your main bread-and-butter. Is it writing?

No, I have my own business making jewelry. I have a store on Etsy and do shows. It’s called Malaprop Designs. I usually screw up phrases. I’m really careful in my writing and I have to check with someone: did I say that right? I’m an unintentional malapropper.

I used to make jewelry too. I found it very meditative.

My jewelry is certainly inspired by the Catskills. It’s not blingy, super-shiny glass baubly stuff. I love to use semi-precious stones and sterling silver. I would say my work is more organic and earthy, not like what you’re going to see at the jewelry store at all.

I started making jewelry because I was aghast at how much jewelry costs. I thought: this has got to be cheaper if I do it myself.

[Laughs] Yeah, that’s kind of how I live most of my life. I can’t afford to buy it, so I have to learn how to make it! I also have a job. I have a part-time gig that I came out of my non-working status to do because it was just a perfect fit. I had been a psychotherapist. I had my masters in social work. I worked for sixteen years in the Hudson Valley in general. My life was diagnosing and treating mental illness and substance abuse disorders and that was definitely one way to pay the bills. It was very intense.

I can imagine.

After 16 years of that, every job I had ever done in the field ended because of budget cuts. So I stopped working and that was when I was doing a lot of freelance writing and jewelry making. Then this job in the hiking community came up. I am the Assistant Program Coordinator for the NYNJ Trail Conference. What I mostly do is create volunteer opportunities and see them through from start to finish. I do everything from identifying the need for a project, to recruiting volunteers for the project, supervising them on the project, rewarding them after the project and – hallelujah – a ton of hiking. I do trail assessment, inspections, help create work plans for whatever we’re going to do on these trails and, it’s definitely work, but it could not feel less like work. It is like joy. Sometimes I have to pinch myself.

Is there such a thing as a day off in country life? And it doesn’t sound like there is for you!

Well, I mean it’s not about so much about the country. When you have five dogs that range in age from fourteen to a puppy, no. I haven’t had a decent night’s sleep since I got the puppy. I’ve always wondered how many dogs would be too many and my current arrangement is too many.

I’m asking this question of everybody lately: what is work?

I think the narrow, more traditional definition of work, as paid employment, really does not fit up here in the Catskills. That’s been the thing I’ve discovered not only about myself, but everyone I interact with up here. That’s something I didn’t expect when I moved up here. Everybody has these complicated work arrangements that involve seven different things. They get paid for some things but not others, although they keep doing them because they love them. Where I come from, that would be really unusual. In this community though, it’s the norm. We’re all doing a million projects and some of them get paid and some not.

To download Heather’s short story, go here and click on the orange box on the right in the middle of the screen. She’s listed at Number 2.

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