Berkshires vs. Cape Cod for late career move? (Boston, Pittsfield: homes, living)

[SWDOC]

Hi all,
I am in my late 50s, single, and recently completed a masters degree to start a new career. I will be entering a profession that is in high demand in many places, so I can pick where I'd like to live. I want to move further north to avoid the harsh summers where I currently live, and love the outdoors, but don't want to be in a very isolated area- a vibrant small or medium town would be perfect. I have been considering the Berkshires or Cape Cod. I love the beach, but several friends have suggested that a single person in their 50s might make friends more easily and find more year-round community and activities in the Berkshires. I love northern NE (VT, NH, ME) but for full-time living am more inclined to stay in MA.

In the Berkshires, the job itself would most likely be in Pittsfield, which I know is not the most beautiful town in the region but I wouldn't necessarily have to live there.

I would welcome any additional thoughts on this dilemma!
Thank you.

[Zephyr2]

They are both beautiful areas, but Cape Cod in the summer is all about boats, fishing, beaches, and often hordes of tourists! The Berkshires are more for hiking, beautiful drives, long winters, and forested nature. Very different. I am someone who loves both the mountains and the sea, but if I had to choose for daily living I would rather be on the coast making visits to the mountains occasionally. To me there is nothing better than pottering down a beach at sunset, or a sail out to the Vineyard or Cuttyhunk. When it gets crazy busy in the summer I go out on the water where you can get away from it all. The winter on the Cape is much, much milder than the Berkshires. If you want real snow and skiing, etc. the Berkshires are better. There are some nice, vibrant communities in both areas. In general, costs will be higher on Cape Cod. I'm not in the market, but for meeting people I always recommend doing it through the activities you love to do. Let's say you like hiking. Maybe join a hiking club to meet people. Or, if you like sailing, maybe join a yacht club. That sort of thing.

[mdovell]

Ugh....uh.....

It's a bit odd to generalize both but with the Berkshires there's upper county, mid and south. With the cape there is cape, upper cape and lower. There's a huge difference between say PTown vs Hyannis and Pittsfield vs say Mt Washington.

sure you wouldn't want Burlington VT?

Anyway despite what some might have suggested most NY'ers fleeing have gone to fairfield county ct and not so much the berkshires. Keep in mind the population of both areas is dropping and the student population has already dropped. I'd argue the roads are much better on the cape vs the berkshires but the traffic is much more. You are more apt to experience salt air on the cape and see bears in the berkshires (first time is scary but after that not as much).

On the cape you are limited on how you get on and off. Berkshires not nearly as much and you do generally have better highway access (at least west and east). There's not much for public transit in either one. I'd also keep healthcare into consideration. the berkshires has lost quite a bit with time the cape not as much but you have faster access to boston technically.

I'd almost argue that the cape would better in the summer and the berkshires in the winter as long as you can deal with traffic. Cape in the winter is pretty empty. Of course covid changed much of this

[P Larsen]

The Berkshires have a great deal more culturally to offer, especially if you consider also that the region really extends into CT's Litchfield Hills and into S VT. About, further afield, equal access to BOS, NYC, Montreal. As you're probably aware, the Berkshires vacationer/seasonal crowd tilts more towards NYC than BOS. While there are beautiful, sublime aspects to the Cape & Islands, I'd say southern RI and East Bay RI offers many of the benefits without fewer annoying aspects. The choicest bit of Cape Cod is one that most people pass over: Sandwich (it has perhaps the most severe development restrictions except for Truro maybe Ptown). As for winter, with a trend towards more ocean-effect snowstorms, the Cape's mildness in the winter is less consistent than when it was more typical to have inland cutter snowstorms, not that the Berkshires is easy in the winter - and winter in the interior Northeast is still a 5+ month affair.

[SWDOC]

Zephyr2, thank you for the very helpful insight! I am also someone who loves both the mountains and the sea and I am glad to hear there are nice, vibrant communities in both areas. My friends (even ones who live near the Cape or summer there) seem to think the Cape dies in winter :-). Like you, the openness of the sea is very comforting and inspiring to me. But, I realized that even if I am doing what makes me the most happy, I want to do it with some other people, so if there are activities I can join year-round on the Cape, that would help.

mdovell, Thank you as well! I love Vermont but somehow Burlington seems too far from everything for me (although it does have an airport!) as i have friends in Northampton, Albany, and the Cape. Of course I will want to make new friends where i go but i'd also like to have access to some of my old friends. I appreciate your point that it's hard to generalize as they are diverse in their own way. Your assessment is very helpful -- it would be nice to have two homes! Maybe some day!

P Larsen -- wow, now I am really curious about Rhode Island! Thanks for sharing all your knowledge with me. I can probably handle 5 months of winter but no more than that :-) Very helpful perspective about the Berkshires' orientation to points north and south, as well as east. And I will definitely consider Sandwich. I don't see myself being able to afford Truro or P/town or even wanting to be that much farther out full-time by myself.

Thanks to all of you!!!

[gf2020]

I'm curious what this magical job is, that is "in high demand in many places".

My advice is always to find the job first and then find a housing location that accommodates your desires within reasonable proximity to that job.

It makes no sense to settle in Hancock or Sandwich, for example, if it turns out your dream job is in Shrewsbury.

[Lampert]

I know the Cape dies in winter and is (was?) one of the worst area for the opioid epidemic in MA..but is that very different from the Berkshire? Are the Berkshire very lively in winter?

[htfdcolt]

Originally Posted by mdovell

Ugh....uh.....

It's a bit odd to generalize both but with the Berkshires there's upper county, mid and south. With the cape there is cape, upper cape and lower. There's a huge difference between say PTown vs Hyannis and Pittsfield vs say Mt Washington.

sure you wouldn't want Burlington VT?

Ah, this thread is making me wistful. I'm not that far removed from the OP's age, but retiring still seems like a dream unfortunately. But if I were, Burlington, VT would be my choice (actually, Monterey, CA would be...but I don't wanna go broke in retirement LOL). It's such an idyllic place, and a vegetarian/vegan paradise which is important to me.

[Zephyr2]

There are lots of other places in Massachusetts that aren't Cape Cod or the Berkshires. I particularly like the south coast area between Westport and Onset. I lived in Westport for awhile and loved it. Horseneck Beach is gorgeous winter or summer. There is a large marina and mooring area near Horseneck to keep an ocean-going boat, or you can paddle for miles up and down the Westport River. Yet, you can be in Boston in an hour or so if traffic allows, Providence is closer. Other places to check out include South Dartmouth, Mattapoisett, Marion, Onset. All have great access to Buzzards Bay and are close to I195 for fast driving to other areas. You don't have to deal with the Cape bridges in the summer too. Somebody did mention Burlington in Vermont as being a great place, and it keeps going year-round. It would be particularly good if you are interested in skiing. Check out parts of upstate New York too. Lake Placid and Saratoga Springs are two great smaller cities that are walkable and have tons of stuff going on.

[SWDOC]

gf2020, my new masters is in mental health counseling. Counseling and social work are in very high demand almost everywhere now. One has to work for a couple of years before getting an independent license when you can really have your own business wherever you want. I would say, in general, health care professions are high growth, as are IT related professions.