St. Michaels, MD

The summer’s approaching, so to get in the spirit Emily and I decided to head out to Maryland’s Eastern Shore to St. Michaels, MD, a quaint town about an hour and a half drive from Washington DC. Even before we crossed the four mile long Bay Bridge over the Chesapeake, I noticed the sand and pine trees characteristic of the coastline. I didn’t like driving over the bridge. It’s really high, the lanes are narrow, and there is no shoulder. I was also in an eastbound lane next to three oncoming westbound lanes, and on my right was a 100 foot drop.

St. Michaels (Talbot St)

St. Michaels (Talbot St)

Just after we crossed the bridge we decided to get lunch at The Jetty Dock Bar, a waterfront restaurant in Graysonville, MD known for its seafood and beach atmosphere.  We’ve been there before and really like it because of its laid back vibe, big menu, and dog friendliness–it even has a dog menu. We sat on the beach area at a covered picnic table and ordered lunch and a couple of beers. I got a crab shrimp plate ($18) and Emily got a veggie wrap ($10). Not the best deal in the world but given the setting I expected to pay up.  Ollie went without food–I had just given him a good meal in the morning. He occupied his time going over to the table next to us and receiving pets and the occasional french fry from admiring fans.

The ride on to St. Michaels took us through farmland and a few roadside farm stands selling in-season strawberries and asparagus.

St. Michael’s one of the oldest settlements in Maryland and it’s a good place to spend a few hours. We walked along Talbot Street, the main strip running through town.

St. MIchael's Talbot St

St. Michael’s Talbot St

Talbot Street is lined with restaurants, art galleries, and souvenir shops. The day we were there happened to be the town’s Strawberry Festival festival, put on by a church.

Strawberry Festival

St. Michaels MD churchyard

In the church yard were about 20 tents with vendors selling all sorts of things. Inside the church community center a bunch of cute old ladies were were selling $4 strawberry shortcake desserts.

St. Michaels Strawberry Festival

St. Michaels Strawberry Festival

St. MIchael's signage

St. Michael’s signage

Emily went into a jewelry store and the employees couldn’t get enough of Ollie; they fed him way too many treats. The town was one of the most dog-friendly I’ve been to. Every shop that doesn’t sell food seemed to welcome our dog inside.

We noticed some dark clouds approaching quickly over the bay, an early warning sign that it was about to pour. The rain came in huge droplets just as we were driving out of town.

On the way home we stopped at Mill Creek Farms (Wye Mills, MD), a market on Route 50. The enormous strawberries, visible from a mile away, coupled with the “Amish Goods” sign were enough to attract us. We enjoyed looking at all the jams (strawberry jalapeno!) , jellies, nuts, spices, etc, along with all the fresh local fruit. I picked up some peanut butter fudge, peaches, maple syrup, and Amish pork sausage; Emily picked up some squash chips, okra, and fresh strawberries. We left Ollie in the car but noticed a sign that “pets need to be leashed at all times,” suggesting that we could have brought him inside. Overall, the place didn’t turn out to be the tourist trap its appearance suggested it would be.

This was our first trip in the DC area as a married couple. Still going well!


Kevin is based in Washington, DC and writes about his travel adventures in the Mid-Atlantic region and around the world. Through entertaining writing and eye-catching photography, he aims to provide readers with useful information as they plan their next trips.

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