Between Baltimore And Philadelphia Is Maryland's Friendly Waterfront Town With Restaurants, Shops, And Trails

From indulging in delicious seafood to relaxing on the waterfront, there's nothing quite like a Maryland vacation. Tucked on a commercial canal on the Maryland and Delaware border — less than an hour-and-a-half from Baltimore, and just over an hour drive from Philadelphia — is Chesapeake City. This tiny town has less than 1,000 residents (778, to be exact, as of 2023) but no shortage of charm, with its 19th-century architecture, friendly atmosphere, lively eateries and boutiques, and idyllic nature.

Chesapeake City is home to a few cozy bed and breakfasts, but for a stay full of historic charm and waterfront beauty, opt for Inn at the Canal. Located in a 1800s Victorian Gothic building, the inn has its very own cocktail lounge, and seven different rooms, and offers breakfast vouchers for Cafe on the Bay, a coffee shop across the street. 

Philadelphia International Airport is Chesapeake City's closest international airport, and is around an hour away by car. The town is a natural starting point for a scenic road trip through charming Eastern Shore towns like Chestertown or St. Michaels, a Chesapeake Bay town that brims with seafood and nautical influences.

Although Crisfield, Maryland, around three hours away, claims to be the "crab capital of the world," Chesapeake City has plenty to offer foodies as well. You'll find a number of eateries in Chesapeake City, ranging from fresh seafood spots to cozy cafes. The waterfront Schaefer's Canal House is one of the town's top spots, with a legacy extending back to the early 20th century. Its menu focuses on the best of Maryland seafood — with dishes like breaded oysters, lobster melts, and of course, crab cakes stealing the show. 

The Tap Room Crab House is another local staple for seafood in a casual atmosphere that has been around since 1981 — just keep in mind that it's a cash-only establishment. If you're more into steak rather than seafood, Prime 225 is your spot. Rated a 4.6 on Google, the upscale restaurant is "out of this world fantastic," to use the words of one reviewer. "Don't hesitate, just go! You will not be disappointed."

The town also houses a handful of charming shops, such as The Mercantile at Back Creek, a goldmine for eclectic gift items, handmade jewelry, pottery, and more. For funky clothing items and accessories, Chick's Boutique is a local go-to, and Chesapeake Candy Works is the perfect place to pick up a sweet souvenir. "My girls liked the Dubai Chocolate as well as the jelly fruit slices. I loved the milk chocolate-covered cherries, perhaps the best I've had in my 41 years!" said a reviewer on Tripadvisor. "We cannot wait to come back!"

Apart from enjoying historic Chesapeake City, don't skip taking in some views of the canal as well. The town lies near the west end of the C and D Canal, which connects Chesapeake and Delaware Bays. It's used by countless cargo ships and pleasure boaters 24 hours a day. The C and D Canal Trail is a roughly 14-mile trail that runs along the side of the canal from Chesapeake City to Delaware City, Delaware. You can walk or bike, and you can walk just a bit of it and turn around if you want a shorter day. "Walking on the trail was a lot of fun," said a reviewer on Tripadvisor. "The terrain was pretty flat, and it was an easy walk." 

To get to the start of the trail, you'll have to get to the north side of town (the town's historical district, with its shops and restaurants, will largely be found on the south side of the canal). To navigate between the two sides, you could drive over the bridge. But for more adventure, just hop on the Chesapeake City ferry, which runs from April to October for just $3 one-way or $5 round-trip. 

For more gorgeous trails in the area, head to Lums Pond State Park, which is around 10 minutes away from town. The park houses four different trails, a nature center, and, from March to December, even a zipline park. You'll also find Delaware's largest freshwater pond here, perfect for kayaking, canoeing, or pedal boating. For another underrated Maryland getaway, also consider a visit to Smith Island, where you'll find cute small towns, fresh seafood, and diverse landscapes.