Relocation Recon: Chestertown, Maryland

Relocation Recon: Chestertown, Maryland

I’ve been planning to move for a while now, and although I’m not sure when — I’ve learned that the best laid plans are easily thwarted — I’ve started to explore some towns where I think I might want to live. I did a lot of research online to identify places that seem to meet my criteria: an East Coast town or small city in a coastal location, not too far north, preferably south (of Pennsylvania, where I now wrestle with too-long, too-cold winters), with a friendly vibe, lively farmer’s market and dining options, artistic community, affordable housing and opportunities for a comfortable livelihood. This is a tall order.

Chestertown marina

Chestertown, Maryland waterfront












That’s why I was delighted to discover Chestertown, Maryland, on the upper Eastern Shore of the Chesapeake Bay. The town blends the coastal features I crave with the surrounding farm fields — and related local food culture — that I’ve come to appreciate where I live now. Its commitment to historical preservation makes the downtown both a lovely place to stroll and an opportunity to imagine what life was like in the early 1700s. Chestertown reminds me of another place I used to live (and loved) — the Old Town district of Alexandria, Virginia — without the urban bustle and crowds.

Chestertown is home to Washington College, which reminded me of Susquehanna University in the town where I live now and where I used to work. College towns are wonderful for their youthful energy, educational perks and cultural events, many of which are free. I only had time to drive through the Washington College campus, but it was very pretty, and I intend to explore it more thoroughly on my next visit.

Chestertown, Maryland home

Viewing a town as a prospective place to live is different from visiting as a tourist. You look more closely at homes. You notice if people meet your eye — and maybe smile — on the street. You talk to locals when you get the chance. And you imagine yourself doing things you love (in my case, taking waterside walks, lingering in an inviting cafe, befriending artists, sipping a glass of wine at a welcoming spot like JR’s Pub) in this new setting.



Chestertown Custom House

This is the old Custom House near the Chester River waterfront, dating to 1746.







Chestertown goose

I can never resist the local creatures in the places I visit.








Chestertown, Maryland fountain

All in all, for me, Chestertown is a serious charmer. I can see myself feeling at home there. I hope to meet more of its residents over the next several months to add to its story. It seems like it would be magical in the fall.









Chestertown waterfront walkway












Have you ever been to Chestertown? What do you think?


(2) Comments

  • Jackie Cangro
    11 Aug 2015

    Chestertown looks like a wonderful town. So charming. I can see why it is high on your list of potential places to live.

    • Karen Jones
      12 Aug 2015

      It really did feel like a good match for me, Jackie. I have a few more places to check out, though, so stay tuned!

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