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.

lots of bricks in #Chestertown,MD from Shalavee.com

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.

My kids enjoying a puppet show in #Chestertown,MD from Shalavee.com
Waving at the Sultana on the Chester River in #Chestertown,MD from Shalavee.com

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.

Charming plantings in #Chestertown,MD from Shalavee.com

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.

The #Evergrain bakery in #Chestertown,MD from Shalavee.com
Inside The Evergrain bakery in #Chestertown,MD from Shalavee.com
Inside The Evergrain bakery in #Chestertown,MD from Shalavee.com
Inside The Evergrain bakery in #Chestertown,MD from Shalavee.com

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.

Charming Houses in #Chestertown,MD from Shalavee.com
A church in #Chestertown,MD from Shalavee.com
Fiona in #Chestertown,MD from Shalavee.com
Fiona's new duck friends in #Chestertown,MD from Shalavee.com
A waterfront home in #Chestertown,MD from Shalavee.com
A walk along the waterfront in #Chestertown,MD from Shalavee.com
Christina and Fiona in #Chestertown,MD from Shalavee.com

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.

The farmer's market in #Chestertown,MD from Shalavee.com
eggs from the Farmer's Market in #Chestertown,MD from Shalavee.com
eggs from the Farmer's Market in #Chestertown,MD from Shalavee.com
 the Farmer's Market in #Chestertown,MD from Shalavee.com
A typical shopper at  the Farmer's Market in #Chestertown,MD from Shalavee.com
better eggs from the farmer's market in #Chestertown,MD from Shalavee.com

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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    1. 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.

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