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From Boston to Asheville: Why I Made the Move

Trading subway cars for mountain trails, tiny apartments for actual space, and finding a pace of life that actually works.

I loved Boston. Let me start there. The walkability, the culture, the international food scene, the energy of a big city doing big things. My tiny apartment in Brookline was perfectly situated - walk to the T, walk to coffee, walk to everything. But after years of academic research at Harvard, years of city noise and city prices and city exhaustion, I needed something different.

The search started simple: I wanted Boston's good parts (walkability, culture, food, progressive values) but with breathing room. Mountains would be nice. Seasons that didn't involve five months of gray slush. A place where my realtor income could buy more than a closet with a hot plate.

The Search

I made lists. So many lists. Burlington was too cold. Portland was too expensive (and honestly, too similar to Boston). Boulder was... Boulder. Charlottesville was lovely but something didn't click. Then someone mentioned Asheville, and I thought, "North Carolina? Really?"

But I visited in October 2018. The mountains were showing off with peak foliage. I walked around downtown, grabbed coffee at High Five, wandered through the River Arts District. It had this energy - creative but not pretentious, progressive but not performative, small but not boring. Plus, I could actually afford to live here.

What I Gave Up

Moving from Boston to Asheville meant accepting some trade-offs:

  • Public transit. The T wasn't perfect, but it existed. Here, you need a car for almost everything.
  • International diversity. Boston's a global city. Asheville's getting more diverse, but it's not the same.
  • Big city amenities. No major league sports. Fewer concerts. No direct flights to Europe.
  • The ocean. I didn't think I'd miss it until I couldn't drive to it.
  • Career options. In Boston, I could pivot careers monthly. Asheville's job market is... limited.

What I Gained

But here's what I got in return:

  • Space. My mortgage here is less than my Boston rent, and I have an actual house. With a yard. And a garage. The luxury!
  • Nature access. I'm 10 minutes from trails. Real trails, not the "nature path" along Storrow Drive.
  • Community. In Boston, I knew my roommates. Here, I know my neighbors, my coffee shop people, my volleyball crew.
  • Pace. Nobody's running for a train. Traffic exists but it's not soul-crushing. People actually make eye contact.
  • Seasons that make sense. Spring arrives in spring. Fall is gorgeous. Winter's mild. Summer's hot but not Boston-humid-garbage-smell hot.

The Gay Thing

I'll be honest - I worried about being openly gay in the South. Boston's so accepting you forget other places might not be. But Asheville surprised me. It's this blue bubble where nobody cares who you love. I wear my jewelry, hold hands with dates, have Pride flags up. It's not Boston's in-your-face queerness, but it's comfortable. Actually comfortable, not "tolerant." There's a difference.

The gay scene here is different - less concentrated, more integrated. Instead of a gayborhood with gay bars and gay coffee shops, you just have... neighbors who happen to be gay, and bars that happen to be welcoming, and nobody makes a thing of it. It took adjustment, but now I prefer it.

The Reality Check

Asheville isn't perfect. The job market is rough if you're not in hospitality, healthcare, or remote work. Housing prices are climbing fast. The city's struggling with growth. August tourists make me understand why locals complain. And yes, sometimes I miss being able to take the Red Line to Cambridge for Ethiopian food at 11pm.

But when I'm drinking my morning cortado on my porch, watching the sunrise hit the mountains, about to head out for a trail run before my first showing... I don't miss Boston. I appreciate what it gave me, but I don't miss it.

Making the Jump

If you're considering a similar move, here's my advice:

  • Visit in different seasons. Asheville in October is a fairy tale. Asheville in February is... different.
  • Be honest about what you need vs. what you want. I needed mountains and space more than I needed the Met.
  • Have a job lined up or be really confident in remote work. The job market here is no joke.
  • Give yourself time to adjust. I spent the first six months wondering if I'd made a mistake. I hadn't.
  • Embrace what the new place offers instead of trying to recreate your old city. Asheville isn't Boston. That's the point.

Five years later, Asheville feels like home in a way Boston never quite did. Maybe it's the mountains, maybe it's the people, maybe it's just having outdoor space and financial breathing room. But when friends visit from Boston and say "I could see myself living here," I get it.

The move from big city to small city isn't for everyone. But if you're feeling that pull toward something different, toward mountains and space and a life that moves a little slower - Asheville might be your place too. Just be prepared to explain to everyone back home that yes, there's culture in North Carolina, and no, you don't miss the T as much as you thought you would.

Dylan Lennon made the jump from Boston to Asheville in 2019 and hasn't looked back (except to visit friends and eat at his favorite Cambridge restaurants).