Fall Getaway: Eastern Shore of Maryland With Kids!

One of the mid-Atlantic’s unsung treasures is the Eastern Shore of Maryland. Located approximately two hours from downtown Washington, DC, the Eastern Shore lies along the Chesapeake Bay and provides an ideal opportunity to get away from the hustle and bustle of the city.

The first time my family visited the Eastern Shore was in the summer of 2010, when we rented a home to celebrate my son’s first birthday. We rented a home via Eastern Shore Vacation Rentals, located down in Tilghman Island, a small island in the Chesapeake. To get to Tilghman Island, you have to cross a drawbridge and once you are in Tilghman, there’s very little by way of things to do.

Drawbridge over Knapps Narrows to Tilghman Island

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Our rental home for the week, the Choptalk Cottage, was located along the waterfront and provided an ideal setting for celebrating my son’s first birthday, complete with a Smith Island Cake, the state dessert of Maryland.

amazing layers hidden inside the Smith Island Cake

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A few years later, we decided to return to the Eastern Shore, but instead, visited in mid-October as our annual family fall getaway. It turns out, the Eastern Shore of Maryland is even more wonderful in the fall!

For our return visit to the Eastern Shore, we again rented a home, Heron Point, through Eastern Shore Vacation Rentals. Both rentals were as described and when we had issues with the internet service during one of our stays, the company was happy to send someone out to help us reboot the modem and get connected even though it was a Saturday afternoon. We did not, however, rent the same house we rented the first time, choosing instead to rent a home closer to Easton, Maryland, the county seat and where our dining options would be less limited.

Situated on three acres along the water, the view from our rental home was outstanding. Not only was there ample space for our family to enjoy dinners together, but we also loved sitting outside and just observing the world around us.

one of the many dinners we enjoyed

view of the dock from our rental home

My young son particularly loved the opportunity to be outside in the fall and we visited Council Farms, one of the best pumpkin patches we have ever been to – one where the pumpkins were still on the vine!

running through the corn maze

checking out the manual apple press

What little boy doesn’t love a tractor ride?

In addition to Council Farms, we also visited St. Michael’s, a small coastal town that offers plenty of opportunities to shop and dine. The Eastern Shore Brewing Company is located at one end of the main drag, so of course we stopped in to sample some brews.

A few things to note about the Eastern Shore:

• Traffic can vary significantly depending on your departure/arrival times and, on occasion, the Chesapeake Bay Bridge, which you must cross to get to the Eastern Shore from DC, can close when there are high winds. In an attempt to avoid heavy traffic and delays, we usually leave very early in the morning to head out to “the Shore” and plan on spending a few hours visiting St. Michael’s or just puttering around somewhere instead of attempting to time our arrival with when the rental home becomes available (usually 3pm).
• The Chesapeake Bay Bridge is a very long bridge and can be intimidating to drive across if you are, say, from California and nervous about earthquakes. If you are uncomfortable driving across the bridge, there is a drive-over service that you can call one hour before your arrival. Although I have not personally used the service, I have friends who can recommend it.
• If you happen to be visiting the Shore in the summer, make sure you feast on some Maryland Blue Crabs. Although there are places where you can get Maryland Blue Crabs in DC, nothing beats getting a bushel of crabs and eating them outside along the Chesapeake Bay!
• If you aren’t one for vacation rentals, the Hyatt Regency Chesapeake Bay may be a good option for you. It’s not only kid and pet friendly, but it has a number of options for the kiddos, including family portraits, evening s’mores, and more.
• There are a number of restaurant choices in both St. Michael’s and Easton, but St. Michael’s in particular can get very busy during peak tourist season so expect a wait! Luckily, because it’s a heavily visited area, everyone is familiar with children and accommodating.

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