Winter Wonderland by Jennifer Cleary in Chesapeake City, Maryland

The small town of Chesapeake City is full of history and breathtaking scenery. The locals here know, however, that the town itself isn’t the only photographic gem. Just a ten minute drive away off of Highway 213, I’m at the edge of a small channel off the Bay—named the Bohemia River—and facing right into the sunset. Trees shaken bare for the winter offer a nice contrast to the explosion of pinks and oranges over the water, and, in the distance, I can make out the soft glow of the nearby marina’s lighthouse. I have been here for well over an hour and I’ll stand long after the sun has set, capturing every moment of color until there is nothing but black in my lens. I must’ve snapped well over one hundred pictures, but the beauty of this place is that the image is always changing—always a new color, a new angle, a new subject that has entered the frame. I have come to this spot many times in my life and have essentially never captured the same photograph, which makes it that much more exciting and beautiful to visit. In these moments, I am truly home.

Name:Jennifer Cleary

Former flight attendant, soon-to-be intern for Trail Runner Magazine


Writing freelance travel and outdoor articles, running trails along the river, taking pictures (of course), and planning for my temporary move to Colorado.

Tell us about the place you live:

Chesapeake City is one of the most picturesque areas in Maryland (and that’s not just me being bias towards my hometown). The town itself—with its locally owned shops and restaurants—is split neatly in two by the C&D Canal bridge, and makes for stunning pictures in ice, snow, rain and sun. The Canal connects the Chesapeake and Delaware Bays, and so it is not uncommon to see one of the massive cargo ships passing by or the native waterfowl flying over colorful boats. A definite tourist spot for seafood, water activities and boaters, we have the luxury of being called a “city” without the crowds or the closed in atmosphere. If you stay long enough, you’ll likely become another familiar, friendly face to us locals and you may even be invited to a fancy yacht party.

A perfect day?

A perfect day would start with a jog or bike ride along the Canal on the North side, then heading over to the South side for breakfast at the Bohemia Cafe. Meander throughout the streets and check out the locally owned shops, then grab some seafood or a burger at the famed Chesapeake Inn. Compliment that fantastic lunch with a scoop of ice cream from the Canal Creamery, then take a boat ride down the Canal. Finish off the day with a glass of wine overlooking the water and sunset at Schaefer’s Canal House.

What is the best thing about your spot?

Here in Chesapeake City, the food is a must. You may have already heard that Maryland is known for their blue crabs, and this town doesn’t disappoint—get ’em steamed, soft-shelled, in cakes, and sprinkled in good ‘ol Old Bay.

What is the worst?

If you’re looking for chain, department, or grocery stores, you’ll have to drive about 15 minutes away.

What would be surprising about this place to an outsider?

You can actually walk across the C&D Canal bridge (there is a sidewalk on the right side—just be prepared to climb up a lot of steps!)

If your city was a person or character who would it be?

Bambi—peaceful, quiet, beautiful.

Who are three of your favorite artists?

Chris Burkard, Bleachers, Kiel James Patrick


Name:Jennifer Cleary

City:Chesapeake City

Favorite place to eat:

Chesapeake Inn

Favorite place to drink:

Bohemia Cafe

Local Tip:

Order your french fries sprinkled with Old Bay and try a “Natty Boh” (National Bohemian beer).

Must Do:

Take a canal cruise with M/V Bay Breeze, check out the Hole in the Wall bar, and (if visiting in December) do the Christmas Candlelight House Tour.