When Mark and I began to look at houses on the Eastern Shore of Maryland, we took a look at Chestertown. This fabulous little town perched on the Chester River is chock full of historical houses and charm oozes from every crack between every brick.

It was a little far from our appointed distance to DC work radius but charmed is charmed.
I have had occasion to make some return visits recently. The first time with my friend Amy and her boy who’s my son’s buddy. There is an annual May weekend festival called the Tea Party in Chestertown.


A puppet show, fried food, and a chance to sit by the river to wave at The Sultana as she sailed by. Fun.
I then returned the third weekend in June to visit the famed Chestertown Farmer’s Market and catch up with newlywed Christina. See the fabulous pictures of her wedding in this post.

The town has really bloomed since we first visited there 14 years ago. Many of the houses have been renovated making it a destination retirement village of a sort for monied and artsy types. Because the price tags on these charming restored residences are phenomenal. Christina’s watching all the listings while she lives in a charming teeny tiny house.
There’s an Arts Center, the same little coffee shop called Play It Again Sam, and a new and very popular bakery/coffee place called Evergrain Bakery Company.




Chocolate croissant and a baguette for me. Baguette and coffee for Christina. People watching for Fiona. Fiona was so full of herself standing in the middle of the crowd queued up for croissants and café au lait.
Young owner, great story.







Fiona, Christina, and I strolled around town taking pictures and making friends. And then came back through the market to pick up a few things. Her sister was selling her organic eggs and Christina bought me the loveliest colored dozen of eggs I’ve ever had.






Such a nice day. A great destination for a jaunt, a stroll, and a Farmer’s Market kinda Saturday with charming company.
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Those eggs are divine! Looks like a very sweet town — I would love to stroll it with you ladies 🙂
Jennifer, You and I are destined for a strolling destination together. You do seem to get out and really enjoy some lovely little places yourself. Yes, Chestertown is so remote and charming, it was worth the hour jaunt. I am ready to go back today.
Love,
Shalagh