Two Years Later, I Was Still Thinking About Chestertown

About two years ago, I visited the Chestertown Farmers Market for the first time.

Here I am, two years later, still thinking about it.

That may sound a little ridiculous, but if you've ever stumbled across a place that just clicked, you probably understand.

I've visited farmers markets all over the country—including some incredible ones in San Diego and Santa Barbara—and Chestertown still ranks right up there with the best of them. When a farmers market is still popping into your head two years later, you know it did something right.

So when I recently found myself with a free Friday morning, Chestertown immediately came to mind.

Located on Maryland's Eastern Shore along the Chester River, Chestertown is one of those towns that feels like it hasn't forgotten who it is. The historic buildings, brick sidewalks, locally owned shops, and riverfront views all work together to create a place that's charming without feeling touristy.

And somehow, despite being less than one hour from home, it feels like a little escape.

Since I was visiting on a Friday, the farmers market wasn't happening, but I decided to spend the day exploring town instead. And honestly, that turned out to be a pretty perfect plan.

My first mission?

Bakeries.

If you've followed Our Town MOT for any length of time, you probably know I have a weakness for a good bakery. So I decided to make things interesting and hold an unofficial Chestertown Bakery Competition.

Three bakeries entered.

One bakery left with the title.

The winner was Evergrain Bread Company.

Their raspberry chocolate croissant was absolutely delicious. Flaky layers, rich chocolate, a little tartness from the raspberry—I knew after the first bite that the bakery competition was over.

I may or may not still be thinking about it.

A close second place goes to this bakery here....

After satisfying my bakery obsession, I spent the rest of the morning doing what Chestertown does best: wandering.

The downtown area is full of interesting little shops, historic homes, and beautiful streets that seem designed for strolling. I popped into stores, admired old architecture, and found myself slowing down in a way that rarely happens during everyday life.

At one point, I realized I wasn't really headed anywhere. I was simply enjoying being there.

Chestertown has a long history dating back to 1706, when it was established as a colonial port town. Today, much of that history is still visible throughout town. It's also home to Washington College, founded in 1782 and one of the oldest colleges in the country. George Washington supported the school and even lent it his name.

History isn't usually the reason I choose a destination, but it certainly adds to the character of this one.

Eventually, I made my way down to the riverfront.

The Chester River is beautiful, and the waterfront area makes it easy to stay awhile. Boats drifted by, families relaxed along the water, and there was a playground where kids could burn off some energy while parents enjoyed the view.

As I walked along the river, I kept thinking the same thing:

I need to come back on a Saturday.

Because as much as I enjoyed my Friday visit, the farmers market is still what makes Chestertown stand out in my mind.

From what I remember, it seemed like every farm on the Eastern Shore showed up. Fresh produce, flowers, baked goods, meats, cheeses, handmade goods, and local products filled booth after booth.

It's the kind of market where you come home with far more than you planned to buy.

In fact, I've already started talking about bringing a group of girlfriends back for a Saturday morning outing. My vision is simple: arrive early, grab a hot chocolate, browse the market, wander through town, and maybe sample a bakery or two along the way.

Or three.

No judgment.

If you've never been to Chestertown, I'd absolutely recommend adding it to your list. Whether you're interested in history, shopping, bakeries, river views, or simply spending a day somewhere that feels a little slower than everyday life, it's worth the trip.

I'm already looking forward to my next visit. And this time, it'll definitely be on a Saturday.