Where Do I Belong: Finding the Right Place to Retire and Create

State map by Andrejs Kirma from Noun Project. A red heart is placed on the map.
State map by Andrejs Kirma from Noun Project

I’ve never lived more than thirteen miles away from Yankee Stadium. 

As I enter my “third act” I’m feeling psychologically ready to retire, which impels me to ask the question, “Where do I want to live?” 

I’ve spent parts of the last 16 summers in the Berkshires. The Berkshires is a highland region mostly located in western Massachusetts but bleeding into parts of New York State and Connecticut. I became familiar with the area when I would visit friends who have a home on the New York side. We’d often cross over to the Massachusetts side where there are more options for restaurants and cultural attractions. In fact, that part of Massachusetts is known for its artistic offerings, particularly in the summer months. As a lifelong city dweller and someone who never enjoyed driving, I always appreciate that’s it’s only a little over a two-hour trip. 

To me, the Berkshires represent a more laid back way of life. Some of the things I noticed after spending some time there, were:

The physical landscape
I can see the stars at night, virtually every night, a rare phenomenon in the city. 

People seem less worried about their property
Friends who live there often tease me for locking my car. 

Activities of daily living are less stressful
A particularly illustrative incident took place on a trip to the post office in Lee. I drove to the post office, parked out front, went in. There was no one in line. The person behind the counter was courteous and efficient. The whole transaction lasted a few minutes. This same trip in my neighborhood would involve a long and frustrating search for parking; making sure I had coins for the meter; standing in a long line, only to have someone wait on me who was equally stressed by the long line of equally frustrated people. 

How would this move impact my creative life?
The draw of a different way of life is appealing despite being a born and bred Bronxite. But as much as I’ve come to appreciate the opportunities afforded to me in the Berkshires, as a “culture consumer,” as a potential full-time resident there is much to consider. I’m rarely there in the winter so I escape the vagaries of the climate which is somewhat harsher in the winter than it is further south. Also because I’m visiting, I’m not aware of the issues facing people living in the communities in which I’m only vacationing. I don’t know the politics.

I also need to consider how this potential move will impact my creative life. For a long time I’ve been fortunate to be part of a network of theatre makers in Westchester County, NY (and its environs) who have staged my plays and given me the opportunity to direct, and on occasion, act. These connections took me years to establish. 

What would it mean to relocate to an area where I don’t personally know anyone who is making theatre? (I don’t know anyone there. Period.) The professional theatres that I patronize over the summer like the Williamstown Theatre Festival and Shakespeare & Co., import most of their talent from NYC, or from those who have established local roots, and I’ve yet to identify community theatres in the area.  

With a retirement goal of spending most of my time in creative pursuits, this issue becomes extremely important. So what to do? To paraphrase Moses (or Robert A. Heinlein), I would be “a stranger in a strange land.” 

Please don’t tell me to start my own theatre. After having longtime leadership roles in two non-profit arts organizations, and running a community theatre — I’m done. (I’m not retiring so I can worry about workers compensation premiums, or whether there is toilet paper in the bathrooms).

So I have this idea of where I’d like to live but little idea how to enter the creative community there. Sounds like I have some legwork to do. Who knows what I’ll find if I do some digging? I don’t know how I’ll fare living in New England. I might really embrace it being there more than two weeks at a time. I’ll just never be a Red Sox fan.