As much as I love living in Newburyport, part of me still misses Boston. Every time I visit my Boston office, I walk through Beacon Hill, admire the brownstones, and occasionally check Zillow to see what’s available, even though it’s really not in my near-future plans. Then I remember what it was really like to raise young children in the city. 

Don’t get me wrong. Boston is an incredible place to live, and I wouldn’t trade those years for anything. But there’s a big difference between enjoying Beacon Hill on a carefree Saturday afternoon in your late 20s and carrying groceries uphill with a baby strapped to your chest in your 30s. 

My wife, Jenn, and I eventually faced a decision familiar to many Boston families: Do we stay in the city we love, or move somewhere better suited to the life we’re building? For us, moving from Boston to the North Shore wasn’t just about finding a bigger house. It was about recognizing that our priorities had changed.

Sometimes Boston Feels Like Life on the Hardest Difficulty Setting

Before kids, living in Boston was fantastic. The restaurant scene, sporting events, walkable neighborhoods, and the ability to head out for dinner without getting in a car. There was always something happening. Then we had children, and suddenly the things we loved about city living became a little less convenient.

I remember hauling groceries up Beacon Hill with a baby carrier strapped to me. What used to be a simple errand suddenly felt like an obstacle course with a tiny human attached. But nothing puts the difference into perspective quite like returning home from a family vacation.

Imagine driving back from a weekend in Maine. It’s 9 p.m. on a Sunday, the kids are asleep in the back seat, the car is packed with luggage, and everyone is exhausted. When we lived in Boston, coming home meant figuring out where to park, getting the kids upstairs, unloading the bags, and possibly heading back outside to find another parking spot. If we ended up at a meter or somewhere with street-cleaning restrictions, another problem waited for us the next morning. Those scenarios usually turn into one headache after another, and most parents don’t want to deal with them after a certain point. 

I sometimes describe raising a family in Beacon Hill as playing life on the hardest difficulty setting. It was still a great life, but I wondered why we were making everything so complicated. Today, we pull into our driveway in Newburyport, carry the sleeping kids inside, and deal with the luggage whenever we’re ready. That might not sound like a major lifestyle upgrade until you’ve experienced the alternative.

Moving to the North Shore Doesn’t Mean Giving Up Boston

When we first considered leaving Boston, I worried about everything we’d miss. We had always enjoyed visiting the North Shore on weekends. We’d head to Appleton Farms, spend time at the beach, or explore communities like Newburyport. Eventually, we realized the places we drove to on weekends might be where we wanted to live.

And here’s the funny part: Our car still drives in both directions!

Instead of spending weekends driving north from Boston, we occasionally head south into the city. We visit the Greenway, go to museums, catch a game, and enjoy everything we used to have outside our front door. Boston hasn’t disappeared from our lives. We’ve simply changed how we experience it.

It’s something worth remembering when considering a move from Boston to the North Shore. You don’t necessarily have to give up the things you love about the city. Sometimes, you just get to enjoy them differently.

My First Patriots Season in Newburyport Almost Sent Me Back to Boston

Of course, adjusting to North Shore life wasn’t completely seamless. Shortly after moving to Newburyport, I was excited to watch the Patriots’ season opener. I found a local restaurant advertising that it would show the game. Perfect, I thought. I could still walk downtown, grab a drink, and watch Sunday Night Football. Well, not exactly.

Around halftime (I remember this vividly), the server came over and mentioned they were preparing for last call. Last call? The game’s only half over! I pointed out that they’d advertised the game, but apparently Sunday night closing time wouldn’t change just because Tom Brady was playing! I wandered over to another restaurant hoping to catch the second half, only to discover they were closing too. Eventually, I gave up and watched the rest of the game at home – it was a defeated feeling. 

I remember thinking, What have I done? Did we really move somewhere that closes before Sunday Night Football ends!?

A few years and a couple of kids later, I understood things differently. Maybe Newburyport wouldn’t replicate everything I loved about Boston. But that wasn’t why we moved here. We moved because our priorities had changed. And sometimes, finding a better fit means accepting that not everything will be exactly as it was before.

Homeownership Isn’t a Golden Ticket to Financial Freedom

Owning a home can build equity and provide long-term financial stability, but it comes with responsibilities renters don’t always have to consider. Property taxes, insurance, and unexpected repairs (just to name a few) add up quickly! Unlike renting, homeownership can make it harder to relocate when your circumstances change.

Don’t assume moving out of Boston automatically means spending less. Desirable North Shore communities like Newburyport, Salem, or Marblehead have their own competitive housing markets, and the lifestyle that attracts families to these areas often comes with a substantial price tag.

That’s why I encourage families to look beyond the initial mortgage payment estimator and consider the bigger picture. Will this move actually improve your quality of life, and can you comfortably afford everything that comes with it?

I’ve shared more about our family’s home search in my accompanying article, So You’re Leaving the City? “Let’s Buy That One, Dad.” That story focuses on how we eventually found our home in Newburyport. Still, another important lesson is that finding the right house and making the right financial decision aren’t necessarily the same. The goal isn’t simply to become a homeowner; it’s to find a home that supports the life you want without putting unnecessary pressure on your financial future.

Sometimes Being Optimized Means Changing Your Priorities

I often talk about the difference between being all set and being optimized, and being all set means you can afford your lifestyle, pay your bills, and save for retirement. Being optimized means making sure those financial decisions still support your priorities as life changes.

Before kids, Jenn and I loved Boston’s convenience/lifestyle. After becoming parents, we valued more space and quality time together. Those benefits might not show up on a financial statement, but they certainly improved our quality of life. 

Take a look at my Parents’ Corner page, which helps families understand their financial responsibilities without losing sight of their long-term goals. 

We Didn’t Leave Boston Behind; We Just Found a Different Way to Enjoy It

I wouldn’t trade our years in Beacon Hill or our decision to move to Newburyport; Boston gave us incredible memories, while the North Shore gave our growing family the space and flexibility we needed.

We still enjoy everything Boston has to offer, just without the challenges of raising kids in the city. And whenever I start missing our old neighborhood, I remember hauling groceries uphill with a baby strapped to my chest!

If you’re considering moving from Boston to the North Shore or navigating another major life change, as a family financial planner serving Boston and the North Shore,  I’d be happy to help you think through the financial considerations.

Connect with Scott to start the conversation.

Securities offered through LPL Financial, Member FINRA / SIPC. Investment Advice offered through Flagship Harbor Advisors, a registered investment advisor. Thrive Wealth Strategies and Flagship Harbor Advisors are separate entities from LPL Financial.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.