Moving to Martha’s Vineyard: Living the Dream ...and Learning to Love the Reality

Have you always wanted to live on Martha's Vineyard? Here's a take on taking that plunge.


Ever since I can remember, I’ve dreamed of living on Martha’s Vineyard.

I grew up spending summers in Chilmark; Menemsha is my Shangri-La. I have precious memories of sitting at Dutcher Dock, breathing in its trademark scent of brine and decaying lobster bait (a scent I totally love now, by the way), racing to gobble up a Texaco Station-bought fudge bar before it melted, netting and releasing shiny minnows with my sister, late-night squid-jigging with the older kids (who were super-duper-cool, as all older kids are to 7 year olds), and watching the fishermen unload their trawls — the thrilling bonus being when they would let us take tiny live crabs from the by-catch (...which we, uh, responsibly dropped back into the ocean afterwards? Let’s just say that.)

So, yes, Menemsha — and the entire island — has always held a special place in my heart. I never had to think twice when someone asked, “What’s your favorite place on earth?” Every time I visited as an adult and was moved by the beauty of the sunset on the ocean or the sound of a horse huffing outside my B&B’s window* I thought, “I will live here one day.”

Alas, it didn’t seem likely. I was a busy New Yorker, and, later, a busy (Los) Angeleno — and I certainly didn’t have the means to buy a house on the island. Martha’s Vineyard was relegated to a “one day, when I’m mega-rich” pipedream. Though I didn’t dwell on it, it manifested as a dull ache; a longing for the unattainable.

Several years ago, when my folks finally decided to become year-rounders themselves (technically they’re off-seasoners, as they rent their house out and have to go elsewhere in the summer), I was happily ensconced in my own little world three thousand miles away. It was years before I even got the chance to visit.

Then, another dream I had — to write a novel set on the island — became a reality. I was fortunate enough to have time to focus on it, so I flew across the country to hole up in my parent’s spare room for a month. You know that totally unrealistic life-as-an-author romantic cliché? I was living it! There I was, perched at a window overlooking the woods of West Tisbury, just me and my laptop and a strong cup of coffee, the only obtrusive sound the occasional cry of a wild peacock. (Which, if you’re wondering, sounds like, MAY-YAWWWWW!)

This was when I said to myself: “This! This is all I want in life.” And then the peacock said, “MAY-YAWWWW!” Which I’m pretty sure in Peacock means “SO DO IT ALREADY!” (Or maybe it just means “CHECK OUT MY AWESOME FEATHERS, YOU GUYS.” Then again it could have multiple meanings; perhaps it’s the “Aloha” of the bird world. You don’t know.)

So, under the advisement of this wise (or just noisy) peacock, I did it. Without being mega-rich (or rich in any degree), I up and moved to Martha’s Vineyard. I’m making it sound much easier than it was: I had to endure some drastic, painful changes; it took a lot of time, sweat, tears and desperate pleas for cheap housing, but one sultry August day I arrived in Vineyard Haven harbor with a suitcase in my hand and stars in my eyes.

And that's when my romance died in the arms of cold, hard realism.

First of all, the minute you move to a place you love, the bloom is off the proverbial rose. It’s not your private nirvana anymore. It’s not the peaceful paradise your mind defaults to when, say, the dentist is drilling your molar and hitting a nerve. It’s your HOME. Which means it’s suddenly a real place, with real people (15,000 of them), real problems (some of which are yours, because this time you couldn’t leave them behind), and while you may drive the entire span of the island twice a day on vacation, you won’t be doing this anymore when you live here, because you live here, and you can see Menemsha anytime now. Why waste gas today?

Second, for some reason I decided to move here in the height of high season, and I hadn't experienced this island in the summer since I was a kid. The crowds made me agoraphobic. As a new resident, it took me exactly 1.1 weeks to start grumbling about the tourists. I couldn’t park anywhere. And the mopeds! Are you kidding me with those things? Get off my roads, you people with your fun-having! I LIVE HERE NOW!

Third, my book wasn’t selling, even with an agent pitching it high and low, so I wasn’t going to be Rowling-rich any time soon. I would have to get a job, and any job would do; I was ready and willing to wait tables or be a barista, but the Vineyard in mid-summer is already stuffed to the gills with work force. There weren’t any jobs out there. I had to wait until September, when all the kids went back to school. (Assuming there were any year-round jobs for the taking, what with most places shutting down for the off-season.)

The island is oddly contradictory — or, a typical tourist spot come to think of it — in that it has a cachet of being a playground for the fabulously wealthy, and yet the year round residents actually average among the poorest in the state. So when I tell people I’m living on Martha’s Vineyard, there’s always an, “OooOoooh, I seeeEeee.” They think I’m golfing with Obama or something. On second thought, I should just let them think that. We all should. But I digress.

There was an article in a U.K. paper recently that, you know, DARED to expose the SEEDY UNDERBELLY of Martha’s Vineyard. It was melodramatic and one-sided and unintentionally hilarious, but it did prove the point that like anywhere else, this misunderstood paradise has its share of poverty, drugs and crime. (Not very much crime, though. I mean, the biggest news story last month was about a couple of dogs who ate some geese. Really. Dogs vs geese. I can hear the LAW & ORDER: MV** line now: “Looks like this perp is FOR THE BIRDS”. dun dun!)

That said however, unlike anywhere else, there is a tremendous and inspiring sense of community here. I think it’s because we share the feeling that we're all in this boat — or, on this “rock” as the natives say, usually with disdain — together. I found a job in September and lucked out: I love everyone I work with, and because it’s a counter position I meet new people every day. Some customers have become close friends. No year-rounder thinks you’re beneath them when you serve them coffee — just about all of us have (or have had) menial jobs, and we don’t feel confined or defined by them because we usually have something else going on, like burgeoning side businesses, or gigging bands, or book deals (< wishful thinking on my part).

In other words, I can’t complain. Not about any of it. I'm thrilled to be here and infinitely grateful to be a part of this wonderfully wacky community. Though My Enchanted Isle has been slightly tarnished by the mundanity of everyday existence, it’s still enchanted. I feel it every time I see a breathtaking sunset, hear a peacock, or make that long trip out to Menemsha to smell that sweet, sweet fishing dock funk.

Martha, even though I know you a little better now — and I have some of your underbelly seeds in my teeth — you’re still my favorite place on earth.


Next post: how to survive the off-season in three easy steps!***


* - Captain Flander’s House. Horses chillin’ outside while you’re taking a nap. It’s amazing.

** - There is no such show, but we should totally make it. LAW & ORDER: MV. Who’s with me?

*** - Or possibly twelve.

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Mathea Morais (Editor) March 26, 2012 at 02:49 PM
Jen, I love this post so much because I went through the same change in emotions moving from "summer girl" to official wash-a-shore. When the Island goes from being a sanctuary to every day reality, it loses some of its shine. But then my relationship with it became more real and the love became more real as well.
teri pirozzi March 26, 2012 at 03:00 PM
Love your journey! As seasonal owners for 20 years, weekly commuters for 4 years (from Arlington MA), when our someday dream of living full-time/year round on the Vineyard, became our best economic choice after the market crash of 2008, despite all of our economic challenges when we first arrived, our love and appreciation for the lifestyle, the beauty, and most of all the community has only deepened. You can't put price tag on waking up every morning on the Vineyard.
Michael West March 26, 2012 at 03:23 PM
Welcome to the island, Jen! I love your energy and positive outlook and surely your manuscript eventually will land somewhere congenial, given the writing gift you clearly have.
Kristin Zern March 26, 2012 at 03:34 PM
Such a wonderful description of your personal journey. Our journey was also about our many friends that we've known since childhood both islanders and summer residents. Many of our summer friends were retiring to the Vineyard. That meant the renewal of real friendships and being part of a wonderful community. Being part of this year round community is unbelievably special.
Jen Zern March 26, 2012 at 03:43 PM
"But then my relationship with it became more real and the love became more real as well." - yes! - and I think this is because finding your niche in a vibrant community like this one is so rewarding.
Jen Zern March 26, 2012 at 03:44 PM
No, you certainly can't! I'm loving taking on the challenges almost as much as I love reaping the rewards. (Almost.) Thanks for sharing your thoughts. :)
Jen Zern March 26, 2012 at 03:47 PM
Thanks so much, Michael! I appreciate the kind and heartening words!
Jen Zern March 26, 2012 at 03:50 PM
Thanks, Mom! (haha.) It really is special -- so glad you and Dad moved here!
Maggie Dempsey March 26, 2012 at 05:54 PM
Sounds so familiar a story, Jen. My journey here has included growing into homeownership and all the funsies that go along with that like knowing your oil delivery man, figuring out where your septic tank is and who on-island sells all the lightbulbs you might need for all your various lights and lamps. Three years and I'm still learning, and adjusting to the seasonal nature of the island. But one thing is certain, all the struggle and hardship is worth it. I find something to be thankful for here, every day. Welcome, welcome to MV and the Patch blog team!
Jen Zern March 26, 2012 at 06:53 PM
Haha, funsies indeed. Thanks so much for the warm all-around welcome, Maggie!
Carol Lashnits March 26, 2012 at 07:10 PM
Oh, how I can relate, Jen. I too spent time here every summer with my family. I remember when I was about 10 and we were driving to Gay Head. We were coming around the curve by Parsonage Pond up to Alley's. I remember it so vividly. I announced that I was going to live on the Vineyard year round some day. My father said, "What? All the year round people are on welfare." At least he didn't say they're all rich. Was it meant to be that I won one of the first Youth Lots in 1977 and ended up marrying, building a house, having a child, founding IEH, experiencing God and finally ending up a Minister. Was it all part of the plan? Oh, and I was conceived in Edgartown but born and raised elsewhere. Now that's pretty weird, too. We just are all here because we are supposed to be. Welcome, Jen. Looking forward to getting to know you this summer!
Jen Zern March 26, 2012 at 07:18 PM
"We just are all here because we are supposed to be." - I like that theory! And, same here. :)
shawn March 27, 2012 at 01:03 PM
I feel it becomes difficult, because, you go from seeing beauty everywhere, to the reality of work, bringing kids to school, dealing with difficult people,bills etc. We live by the ocean, but have not actually been to the beach for months. My unsolicited advice, have tea on your porch every morning, and when you are rushing to "reality" , just look up...
tjbw March 27, 2012 at 07:04 PM
I am glad that you wrote on this topic because I must admit to being one of those people who went 'oh la la' when I heard about your move to Martha's Vineyard! And I honestly don't know why. I mean I worked at Disney World, so I know what it's like to have people think that means one thing (i.e. 'oh la la') when it actually means another (i.e. the same old daily grind). But what I also know is that it is still lovely to be there, especially because it's a dream realized. So here's to you enjoying yourself and that book deal you will be landing.
Jen Zern March 29, 2012 at 11:57 PM
That's great advice. :)
Jen Zern March 30, 2012 at 12:14 AM
Thanks tj. The Vineyard is a jaw-droppingly beautiful place, but it's easy to take its splendor for granted when you're not just here for fun anymore. And while there are certainly a lot of rich people around (especially in summer), there's an entire (much larger, wouldn't be surprised if it IS 99%) community of workers who build their houses, fix their cars, serve their food, etc etc etc...
Jim Masek April 02, 2012 at 02:57 PM
The Wannabee Story: depends on WHEN a person make the decision to live here year around and "make the Island home". Your story is the "contemporary version" and is helpful advice from experience to those wannabees of today. My story is much like others who have moved here in the DISTANT PAST (1984): 1. bought a small ranch home in O.B. Eastville av. 1/4 acre for $50K. 2. arrived with a pickup truck loaded with carpentry tools & yrs. experience (plus the not unusual teacher's cert. & M.Ed. degree). 3. got a job immediately. 4. sold home for good profit & bought a much larger, nicer home in V.H. where I have lived since 1986. Value now is about 5 X what I paid. 5. do not become tempted to buy a boat you bought on a loan. It can become an anchor around your budget. Buy with cash. So the end of story has all about what skills you bring to the Island, whether your family will front a deposit, whether you can live through dreary winters, whether you are creative to find other creative friends, whether you have what it takes to find work through down times. Thus, multiple skills required for the business cycles. The non-mentioned phenomena; I HAVE NEVER ENCOUNTERED IN THE PRESS, is that if you live here for 26 yrs. it then becomes the flip side of your story: difficult adjustment to move elsewhere; such as where? If you can't answer that question honestly, then you really are an Islander. Jim Masek, V.H.
jms1 August 10, 2012 at 10:39 PM
Love the story and the comments.. visiting here on vacation this week.. and I so understand.. after "living the dream" on the opposite coast SF Bay-and Napa Vly-Seattle and Monterey Coast.. from early 70's-06' we left to create a "new dream" in NC.. just so very happy I've lived and live in some of the most beautiful places in the country..
derek September 22, 2012 at 01:43 PM
my wife and i are gonna visit next summer to look into a possible move. i havent been to the vineyard in 25 years, we recently had a little girl and want to be closer to family spread throughout new england, but we have been living in key west for 10 years and have this island mentaltiy thats impossible to shake. im a chef she is a server/saxaphone player. we have alot of freinds here who do the season up their, waiting tables playing music. Seems alot like where we live now, wondering how much more slow it is in the off season. key west has become more year round since we moved here. loved your blog, any thoughts suggestions, ?
Louisa Hufstader (Editor) February 16, 2013 at 08:20 PM
How's it going almost a year after your blog, Jen? I just moved here myself.
Louisa Hufstader (Editor) February 16, 2013 at 08:20 PM
It's very slow here in the winter, Derek. Many places are closed for the season.
Holly Nadler April 02, 2013 at 03:38 PM
I've always cautioned people that once they move here they will never experience vacation euphoria again. Well, wherever your bills are sent, real life sets in. But even with vacations, I love Rodney Dangerfield's line, "The trouble with vacations is that wherever I go . . . I'm there."
Kimberly Burke, D.C. June 10, 2013 at 10:04 PM
I appreciate the point of view from a new "wash-ashore." It took me forever to realize just how special this place is. Growing up here, I just hated it for so long. When I moved back I had a similar euphoric feeling, which completely took me by surprise! I look at the island a whole new way now and couldn't love it more. I promised myself that I'd look at the ocean every day, especially on frustrating days, to remind me how awesome this place is. We truly are lucky to live here.


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