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48 Hours of Exploration in Charming Chesapeake City

48 Hours of Exploration in Charming Chesapeake City

Boats in the water with the bridge in the background

Standing 240 feet tall, the tied-arch Chesapeake City Bridge towers over its namesake town, like an ever-present rainbow made of steel and concrete. The span carries cars over the Chesapeake & Delaware Canal while providing 135 feet of clearance for large vessels using the shipping lane below.

Shortly after the canal opened to traffic in 1829, Chesapeake City sprung up at the midpoint between the Chesapeake and Delaware bays, offering goods and services for the ship crews that passed through.

Chesapeake Inn from above
Photo Credit: Chesapeake Inn

That maritime history is baked into the cultural landscape that exists today, and outside of the aforementioned bridge, walking through Chesapeake City feels like stepping back into that era in all the best ways. Many of this small town’s wood-frame and brick houses from the mid-19th century have been well-preserved.

And when I say small, I mean it. The handwritten election results for the town council posted in the front window of town hall showed the most popular candidate receiving 139 votes. Homeowners sitting on their porches will offer a welcoming “Hello” as you stroll past. And a new face scribbling in a notebook will get a few friendly queries from residents and business owners.

But don’t think of this place as sleepy. As the proprietor of Chesapeake City Curio told me, this is an “eating and drinking town.” There was ample evidence of that when my wife and I visited on a recent Friday and Saturday and noticed that parking spaces and dinner reservations fill up quickly as people pour in to enjoy a meal and a drink on the waterfront. But there’s plenty of other things to see and do, too.

Outdoor dining at a restaurant
Photo Credit: Mal Baker

Friday lunch: experience a classic crab house

As might be expected in a Maryland town on the water, all the menus embrace the bounty of the Chesapeake.

Our first stop was lunch at the Tap Room, an old-school seafood restaurant on the main street, Bohemia Avenue. This is one of those classic no-frills spots that dot the Eastern Shore: wood paneling on the walls, nautical decor, and tables already prepped for crab-cracking with a roll of paper towels and a sheet of brown paper on the top.

While I opted for the crab cake sandwich, a sturdy take on a statewide favorite, my wife got the Creamy Fisherman’s Chowder, a mix of potatoes, shrimp, clams, crab, cream sauce, and tomato. The sweetness of the tomato blended nicely with the spice on the seafood. Coupled with corn on the cob (drenched in butter and with a healthy sprinkling of Old Bay) and coleslaw (also with Old Bay), her meal was a hit.

Friday afternoon: shopping, exploring history, and meeting alpacas

Chesapeake City has a great collection of gift shops with an eclectic mix of housewares, clothes, candles, ceramics, kitchen supplies, and other goods. Check out The Old Gray Mare Gift Shoppe, The Mercantile at Back Creek, and Brookbend. There’s also toys and candy at Belle on Bohemia, artisan-made jewelry and gifts at My Jewelry Place, women’s fashion at Chick’s, and a nostalgia trip of old toys at Chesapeake City Curio.

We spent the most money in the home studio of artist R. Neil Snodgrass (226 George St.), who sells cards, wall panels, paintings, and prints featuring his original watercolor works. Along with paintings of the town itself, subjects include Maryland waterfowl, landscapes, historic airplanes, and Snodgrass’s pet cats.

Visitors to downtown can also learn about the town’s history at the recently opened Chesapeake City Museum and the canal museum run by The U.S. Army Corps of Engineers, which still oversees the C&D.

Woman with two Aplacas
Photo Credit: Painted Sky Alpaca Farm and Fiber Mill

Next, we ventured to Earleville to visit Painted Sky Alpaca Farm and Fiber Mill for a roughly two-hour tour. It’s well worth the drive, because most of the time is spent hanging out with and petting alpacas. Visitors also learn how Painted Sky turns the fiber into yarn, which can be bought on site.

Friday evening: drinking, eating, and more drinking on the waterfront

On the way back to town, we stopped at the Chateau Bu-De winery (pronounced boo-day) located on the property of the famed Bohemia Manor. Offering a rustic tasting room and a lawn that stretches all the way to the Bohemia River, the gorgeous hilltop setting alone is worth the trip. We also quite enjoyed the tasting menu, particularly the Sweet Blush II, which had strong notes of strawberry and cherry without being cloyingly sweet on the palate.

For dinner, we got a reservation at the Bayard House. If you can, grab a table on the outdoor patio; seating is right on the water, offering a terrific view of the blues, pinks, purples, and yellows of a sunset on the canal. On this particular night, the setting was enhanced by a jazz combo fronted by Bruce Anthony, who took an exploratory approach to standards and covers of classic rock songs. (His take on the great Beatles song “Norwegian Wood” ventured into the psychedelic.)

For our orders we went surf and turf: Caramelized Salmon, covered in a brown sugar rub and Hong Kong pepper sauce, and a petite filet mignon. Paired with a Hole in the Wall, the restaurant’s house pale ale brewed by Baltimore’s Heavy Seas, the meal, the music, and the view were a great way to enjoy the evening.

Our final stop was the Rummur Lounge, one of the places I visited last fall on my quest for autumnal cocktails. Situated in the backyard of the Inn at the Canal, the outdoor bar has lots of space and Adirondack chairs that are perfect for relaxing and watching the world go by. The Barbados Rum Punch — a sweet and tangy drink with Plantation five-year rum, pineapple juice, lime juice, and ginger beer — I had was a great accompaniment to the chill vibe. If rum isn’t your thing, Rummur also has drinks highlighting vodka, tequila, or bourbon, as well as beer and wine.

Saturday afternoon: lunch and a hike

On our second day, we ventured over the canal to the north part of town, home of the sprawling Schaefer’s Canal House right on the edge of the C&D — offering even more sweeping views of the water and passing boats.

A couple looking onto the water
A view of Schaefer’s Canal House from the other side of the C&D. Photo Credit: Shutterstock

We started out by splitting a bowl of Maryland Crab Soup, which came loaded with potato, carrots, corn, green beans, peas, and meat. For a heartier crab dish, try Schaefer’s crab melt, featuring crab imperial, swiss cheese, and bacon bits on a pretzel roll. It was a savory treat, and rest assured that all the strong flavors didn’t overshadow the crab.

Just down the street is the 1.8-mile Ben Cardin C&D Canal Trail offering great views and an easy-to-navigate path for walking, running, or cycling. If you want to cross into Delaware, the path goes all the way to the eastern terminus of the canal in Delaware City.

In need of more locally made drinks, we made the short drive to Bayheads Brewing Company, a small brewery with rotating taps and a welcoming staff. On our visit, the smell of malt filled the room after a brewing session in the back room.

Canal Town Beer Can and Glass
Photo Credit: Bayheads Brewing Company

The beers themselves weren’t so overwhelming to the senses the way some craft brews can be; the Pink Guava, a hazy pale ale, was nicely balanced, neither overly fruity or hoppy.

Assuming you didn’t arrive at Chesapeake City on your own boat, the best and most affordable way to get out on the water is a cruise. Chesapeake City Water Tours books sightseeing cruises, happy hour cruises, and sunset cruises, along with themed events like rum and reggae and brunch mimosas. 

Lit up boats on the water
Photo Credit: Mal Baker

Saturday evening: a happy hour cruise, a tasty meal, and one last drink on the water

We chose the 4 p.m. happy hour option, and while it did have a cash bar (we tried a dangerously delicious punch that blended multiple rums, orange juice, pineapple juice, grenadine, and lime) and a soundtrack of classic rock and reggae, the trip was far from rowdy. Mostly, it was a soothing ride, a way to get some sun, spot historic houses on the shore, and watch the osprey and bald eagles that call the area home. The ride went all the way out to the point where the canal meets the Elk River, at the mouth of the bay, and back. 

The best meal we had on our trip was at Prime 225, a sophisticated, low-key eatery located a few blocks off the canal. What it didn’t have in waterfront views is made up for with beautifully plated dishes and impeccable service. The crab cake — huge chunks of jumbo lump, light on the filler—was impeccable, and paired well with the roasted asparagus and risotto on the side. And the scalloped potatoes that came with my wife’s delicious stuffed chicken, I was informed, reached last-meal-on-Earth status.

Chesapeake Inn Cocktails
Photo Credit: Chesapeake Inn

As for drinks, the place to go is the Chesapeake Inn, which always seemed to be hopping. There are two levels of outdoor seating, and even a large tiki bar on a deck right by the water for the party-hearty crowd. (There’s a dinner menu, too, that includes crab cakes, oysters, sushi, and much more. We’ll have to eat there next time.)

Chesapeake Inn Tiki Bar Sign
Photo Credit: Chesapeake Inn

All the summer staples are here: frozen drinks, buckets of booze, island classics, crushes, beer, and then some. Boasting ample space along the waterfront and gorgeous views of the heart of town, the location is hard to beat.

Lead Photo: Mal Baker

About the Author

Brandon Weigel is a writer and editor based in Baltimore. His work has appeared in Baltimore Fishbowl, City Paper, The Washington Post, and other outlets. When not traveling the state, you're likely to find him enjoying a good whiskey, watching the Orioles and Ravens, or driving his beloved vintage Mercedes.

Maryland Road Trips is a part of Postern Publishing.
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