Considering a move to Portland, Maine area -- thoughts?

I assume you have done your research, but you aren't saving a ton of money specifically in the towns you listed unless you're coming from a Weston or Wellesley.

Portland is an awesome city and the weather is actually very similar to Boston. It has a very similar vibe as well, but a little more laid back. There is certainly still a rat race in Portland though. There is a lot of money up there and they are competitive.

As far as negatives, just be sure you won't have to return to the office more often than once per week. Also Portland is 1/10th the size of Boston. Its not a slight downsize in cities, its a massive downsize. And your towns are suburb/rural as opposed to the suburb/urban mix found closer to Boston.

Also confused about your comment on shuttling kids to practice etc. You are going to be doing a ton more driving living in Maine than in Mass.

But I say go for it!

Are you sure about the "more house for the money" ? My son, and his wife, recently purchased in Portland. The housing market is incredibly competitive with many homes closing for $100k - $150k over asking. And the starting points are not very modest. Do your homework. Good luck!

I'd stay. Your kids already have roots there. You can always vacation in Maine.

Boston area has more going on for kids and you will more likely have your kids gets jobs around there later on(or go to college there) so easier to see each other in future when you enter grandparent stage/golden years.

You can exit the rat race in Boston suburbs as well. Stop comparing yourself to others, stop the extravagant spending, buy a cheap car.....it's very possible. No need to uproot the whole family for that.

Unless you really really hate Boston area(and your kids don't care about moving). If your kids are thriving there id stick it out.

Thanks, helpful. To clarify the kids comment, they play various club sports, with practices all over the metro west because their school district does not really offer sports until HS. So we are driving them 30+ min to practice 4 days/wk. In ME the middle schools offer the sports they play so presumably they will just go to practice after school on the school campus. Seemed like an improvement to us.

And we are coming from a Weston/Wellesley-type town so looks like we can basically trade our current 3-bedroom for a 4-bedroom and another 1000 square feet for the same price.

Yeah, I’m pretty sure. Our (small) house is worth about $1.3M now, and though I agree the market is historically ridiculous right now in the Portland ‘burbs, $1.3M gets a much nicer house there than what we have now based on current listings.

whatever you do, please stay in your limousine liberal elitist bubble in weston/wellesley with 1.3mm dollar homes and "in this house, we believe black lives matter, no human is illegal" signs and DO NOT move to a formerly moderate/conservative area like everyone else is doing to arbitrage your remote pay while you vote for higher taxes that don't really affect you on a purchasing power level as the rest of the population.

Boston isn't a college town.

Just my 2¢ and I probably don’t have a lot to add here.

I’m not a New Englander except our families, meaning my family and my wife’s family, vacation in Boothbay Harbor/Oceanpoint just about every summer. My in-laws grew up in Connecticut and NYC and went to school at Colby. My brother went to Bowdoin. So, vacationing and having the loose family connection to the area is really my only familiarity.

We usually fly into Portland or Portsmouth and almost always stop and eat in Portland and I pick up my rental bike in Portland as well. My immediate impression has always been that the city is very touristy. At least that is how I perceive it when we’re there. That said, we pass through during the season for tourism and the restaurant that we stop at is in a more touristy area of the city. It is pleasant and I am sure that the throngs of people are not there all year long. I also don’t know the city that well except for those peripheral experiences so I probably should not add anything else.

Good luck

One other thing based on the comments above.

My kids did the whole club sports thing and all of them played in college. My daughters play soccer at D1 colleges and my son played basketball at a D3 school. The whole club sports rat race is not a lot of fun so it may not matter to you. My girls played in a competitive soccer league (ECNL) and that is not something that you will find in the Portland area. I don’t believe that access to high level club teams should be a determining factor when moving but for some it might be.

It’s funny how my perspective on club sports has changed once my kids were done with them. It really can be warped with misplaced priorities.

Interesting points, but I think I meant something different by the rat race than you took it. We don’t really do the keep up with the Jones’s thing with respect to material things (that would be a losing battle in our town anyway), but we do really want our kids to have the same opportunities we had growing up (e.g., playing on a HS sports team). Believe it or not, that is not close to guaranteed where we are given early specialization, etc., even for solid athletes. We have the resources to throw at that problem if we want to (hence the club sports) and assume the kids are good/self-motivated enough to make it if we stay, but it is just a massive time-suck among other things. That’s just one example among many in our current town — in general the parenting culture is just insane, and we’d like to be somewhat less insane about it. When we lived in NH during the pandemic, the vibe was very different. Granted, that was a pretty rural area, but it provided an interesting contrast. Looking for something closer to that.

I think your points about the kids likely gravitating back to Boston when they are older are probably right on and worth thinking hard about, but on the other hand our plan was never to retire here anyway (that’s what the place in NH is for, which we’ll keep regardless).

And as to whether the kids are thriving, I think by objective measures they are, but given how easily they adapted and thrived to their school in NH (despite their MA roots), I’m not too worried. And while I definitely don’t hate it here, I’m not from here either, nor is my spouse, and despite living here longer than either of us have lived anywhere else, I still feel kind of meh about it even though it’s certainly got a lot going for it. Also, I’ll still be working here and it’s only two hours away.

OP: Where did you live in New Hampshire during the pandemic? I'm considering a move to southern New Hampshire and am curious why you might move to Maine rather than New Hampshire. Thank you.

Fair enough. I have nephews that live in a super chill small rural area and they play and start on the baseball basketball and football teams so I understand the intent. They are also super athletes and would likely excel anywhere(one was recruited power 5 football).

I believe that athlete specialization and insane helicopter parenting coaching like you describe in your area is overrated anyways. If your kid is a good athlete who tries hard it will work out. So many rich uppity area parents throw thousands at their kid to be a sports star as a kid but once he turns 16 the poor minority who grows taller stronger and faster through genetics blows by him anyways. If your kids are good they will be ok.

I didn't really do expensive bsseball travel teams as a kid but I had an amazing natural arm for pitching. Didn't slow me down or hold me back in my sports career.

Ha! Yeah we don’t actually have the yard sign, but we might as well have, and this is pretty much exactly what we’re going to do. I mean, shouldn’t the fact that American society values our skills highly and that we therefore have significant resources mean we get to impose our values on everyone else? Or does that rule only apply when the vast right wing conspiracy spends 50 years and however many gazillions of $$$ to gain control of the federal judiciary and thereby restore the flailing patriarchy to all its former glory? All I want to do is raise your property taxes a little so my kids can do whatever after school sports they want and take some AP classes.

well at least you are honest your intentions (trying to impose your values on others and raise others property taxes which dont affect you as much since you are a remote worker). Most people like you have too much cognitive dissonance to admit that.

its fine, eventually as enough people like you do the same to this new area you move to in rural maine, the rat race will begin with hyper competitive elitist parents and unaffordable taxes and you will have to move again to another untouched area to start the whole process over again.

We lived in one of the ski towns off I-93 in the White Mountains, where we’ve had a vacation house for a number of years. Pretty good school system actually (though tiny), and we did think hard about just staying there. It was fantastic during the pandemic, but we weren’t quite ready to give up the benefits of city-adjacent living when life returned to mostly normal. We did look at S. NH for this potential move too but none of those cities/towns are nearly as cool as Portland IMO, other than maybe Portsmouth, which is quite a bit smaller.

Thanks for that. Best wishes for you and your family.

My response was intended to be (mostly) tongue-in-cheek, but whatevs. I think the real answer is probably that we’re already too late, and the mass displacement of Real Americans has already occurred in those suburbs and property taxes are already sky-high (and climbing) as a result. So to some extent we’d probably be trading one bubble for another, but just hoping the “hyper competitive elitist parent” dial is more like a 7-8 instead of cranked all the way to 11 like where we are now.

If you're keeping your current high-paying jobs (while adding a super long commute once a week), only considering the four most highly sought-after school districts in the entire state, and looking to add another 1,000 square feet... well, you're not really leaving the rat race, are you?

Even if the middle school sports work out, whatever time you save driving is going to be eaten up by the new commute. And don't forget you'll still need to drive over and pick your kids up from after-school practice.

Yes, all fair points about the lack of benefits from specialization and club sports. To be clear I’m limiting my ambitions to them playing HS sports, not worried about them being stars or playing in college (though I really would love it if they were able to — I loved being on a college team). But it’s crazy enough that even for somewhat niche sports like lacrosse, which historically pulled good but untrained athletes from other youth sports and developed them in HS, something like 90% of the HS team played for private clubs since like 2nd grade. For sports like hockey and soccer, it’s more like 100%, even for the JV and freshman teams. And our town does organize youth leagues in all of those sports, so it’s not like club is the only game in town (most kids do both). Track/XC is probably the only major exception at the HS level, which is why running is the best.