5 Great Reasons to Visit Chesapeake City, MD

June 17, 2022


Located along the C&D Canal in eastern Maryland, Chesapeake City is a small, waterfront town that's perfect for a day trip or weekend getaway. Its historic downtown is very walkable with excellent restaurants and boasts fabulous canal views. In this article, I'll share reasons why you should visit Chesapeake City and some of the fun things to do in this quaint town.

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Why Visit Chesapeake City, Maryland?

With its small-town charm and rich history, Chesapeake City is a great place to visit in eastern Maryland. It makes a great day trip destination from some of the big cities on the East Coast. But it's also an ideal location for a quiet weekend getaway. 

Here are some of the reasons that I think you should consider visiting this picturesque Maryland town.

1) Historic Town & Architecture

History of Chesapeake City, MD

Although settled in the 1600s (by Europeans), it wasn't until after the Chesapeake & Delaware Canal (C&D Canal) was built in 1829 that the town began to expand. As ship traffic increased through the canal, the town grew from three buildings on the south bank of the canal to a busy commercial community. In 1849, the town expanded to the north bank of the canal. For 75 years afterwards, the city prospered.

What's in a name?  Originally, Chesapeake City was named Village of Bohemia, or Bohemia Manor, by colonist Augustine Herman in the 1600s. It was changed to Chesapeake City in 1839 after the C&D Canal was built.

In 1927, the C&D Canal was dredged to a sea-level waterway which meant ships no longer had to stop for the locks in Chesapeake City. This began the decline of the town's bustling economy. Now, Chesapeake City is a quiet town instead of the busy commercial stop it once was.

While visiting, stop by the small Chesapeake City Museum to learn more about the town and see artifacts from early settlers. 

Brick Building in Chesapeake City

19th-Century Architecture in Chesapeake City

As you walk through the town, you'll notice many of the buildings built during the 1800s are still intact. Chesapeake City's historic downtown on the southern bank of the canal is on the Maryland and National Historic Registries.

These well-preserved 19th-century buildings give the town a charming vibe. As you walk around, you'll see plaques on some of the buildings. These signs usually tell you when the building was built and sometimes include its name and original owner.

Historic wharf cottage Chesapeake City

Charming wharf cottage. Plaque reads: Herbert S. Bean, 1849

2) Cruises and Boating Life

As Chesapeake City is located along the Chesapeake & Delaware Canal, it's a great spot to get out on the water on a boat. Plus, if you're sailing your own boat or yacht, you can dock in several marinas located right in town.

Chesapeake City Marina

Chesapeake Inn Restaurant and Marina

Chesapeake City Cruises

When you visit Chesapeake City, taking a cruise along the C&D Canal is a fun way to take advantage of the being right on the water. A couple of companies in town offer sightseeing cruises, sunset cruises, mimosa brunch cruises, etc. You can also book private cruises for events, such as birthday, bachelorette, and wedding rehearsal parties.

Decide which cruise is right for you and book online: 

Chesapeake City Ferry Service

Don't have time for a cruise but still want to ride a boat on the C&D canal? Then, I suggest a ride on the Chesapeake City Ferry. Running from April 15 - October 15, the ferry connects the south and north sides of the town and takes only 5-7 minutes one-way. 

3) Ben Cardin C&D Canal Trail

For almost two centuries, the Chesapeake and Delaware Canal has been a vital water passage on the US East Coast. This 14-ft long, 450-ft (137 m)-wide and 35-ft (11 m)-deep ship canal connects the Chesapeake Bay and Delaware River. Once completed, it cut the water route between Philadelphia and Baltimore by 300 miles (483 km). 

One way to soak in the views and appreciate the C&D Canal is to cycle the Ben Cardin C&D Canal Trail. This paved 15-mile (24-km) pathway runs along the canal from Chesapeake City to Delaware City. The trail is mostly flat and has beautiful water views. If you don't have your bike with you, you can still walk along the trail to soak in the views.

Ben Cardin C&D Canal Trail

Walking on the Ben Cardin C&D Canal Trail in Chesapeake City. 

If you're interested in this trail, I recommend this article on the C&D Canal Bike Trail in Chesapeake Living for an in-depth look and tips.

Building the C&D Canal

Although the idea of a canal in this area was first conceived in the 1600s, it did not become a reality until the early 1800s. In 1824, over 2,600 laborers began to dig out the canal with hand tools, such as picks and shovels, for 75 cents per day in wages.

When it first opened in 1829, the C&D Canal was 10 feet (3 m) deep and 60 feet (18 m) wide with 4 locks. Coastal barges, schooners, and steamboats regularly passed through the canal. In 1927, the C&D Canal was dredged to a sea-level waterway so that ocean-going vessels could pass through the canal. Now, more than 25,000 vessels pass through the canal each year. 

4) Waterfront Dining and Maryland Crab Cakes

One of the best things about Chesapeake City's location on the C&D Canal is its waterfront restaurants. Pop in for a waterfront lunch to watch the ships sail up and down the canal. Or, enjoy the evening with a cold beer, delicious food, while watching the sunset over the canal. 

Sunset at Schaefer's Canal House

Sunset at Schaefer's Canal House in Chesapeake City, MD

Most of the restaurants in Chesapeake City offer a delicious variety of seafood and land dishes. However, I was most thrilled to see crab cakes on the menu when we visited Schaefer's Canal House last summer.

Maryland Crab Cake Sandwich at Schaefer's Canal House

Schaefer's Crab Cake Sandwich

Maryland Crab Cakes

Whenever I visit eastern Maryland, crab cakes are a must-order.  If you can resist the call of fresh lump crab meat seasoned perfectly with spicy Old Bay seasoning and just enough filler to hold it all together, then you're a stronger person than I am! Other crab dishes to try are the Maryland Crab Soup or Maryland Crab Dip.

Pro Tip: Order the Crab Cake Sandwich instead of the entrée. It's usually half the price and the same amount of crab cake. It just doesn't come with the entrées sides.

Chesapeake City Waterfront Restaurants

  • Bayard House: Set in an 18th-century house, this waterfront bar and restaurant offers beautiful views.  
  • Chesapeake Inn Restaurant & Marina: Bi-level canalside eatery serving light fare on deck and an upscale American menu upstairs. 
  • Schaefer's Canal House: Nautical-themed bar and restaurant on the north bank of the canal with a large patio and live bands. 

Pro Tip: If you're sailing on the canal and wish to stop for a bite to eat, you can pull right up to a couple of these waterfront restaurants and dock your boat.

5) Eclectic Boutique Shops

Although a small town, Chesapeake City has a few eclectic boutique stores that shoppers might enjoy browsing while visiting. Many of these shops are located in the historic buildings, so it's also a good excuse to check out the interiors of these buildings.

Historic shops in Chesapeake City

Chesapeake City Shops 

Here are a few shops to check out as you wander through town:

Pro Tip: On a hot summer day, grab some gelato at the Canal Creamery and head across to Pell Gardens Park - a waterfront park in the historic district - to enjoy it.

Getting to Chesapeake City, MD

The best ways to get to Chesapeake City, Maryland are either by car or by boat. 

Driving to Chesapeake City

Located along MD-213 and ~10 miles off of I-95, Chesapeake City is an easy drive from several major US East Coast cities. Even if you're traveling between any of these cities, you could easily stop for lunch and stroll through the historic town.

  • Wilmington, DE: ~30-min drive
  • Baltimore, MD: ~1.25-hr drive
  • Philadelphia, PA: ~1.25-hr drive
  • Washington, DC: ~2-hr drive

Sailing to Chesapeake City

Given its waterfront location, it's also possible to sail to Chesapeake City. Town docks are available on a first-come, first-serve basis and a couple waterfront restaurants have docks.

Places to Stay in Chesapeake City, MD

If you live within a couple hours' drive from Chesapeake City, it's an easy town to see on a day trip. However, if you prefer to spend the weekend and or relax for a couple days, you'll be happy to know Chesapeake City has a few places to say in town.

Chesapeake City Accommodations

In this historic town, you'll find a few bed & breakfasts and also a couple of vacation rentals. Here are a some accommodations to check out for your stay:

  • Inn at the Canal Bed & Breakfast: Charming bed & breakfast in an 1800s Victorian house with canal views and free breakfast. 
  • The Checkered Rabbit: A two-bedroom apartment in the historic downtown within easy walking distance of restaurants and shops. 
  • Blue Max Inn: Built in 1854, this charming bed & breakfast is right in the heart of the historic district.
  • Ship Watch Inn: Waterfront bed & breakfast on the canal with beautiful water views from the rooms. 
Ship Watch Inn Chesapeake City

Ship Watch Inn 

Other Accommodations

Use the map below to find other accommodations in Chesapeake City, Maryland or zoom out to see places in nearby towns.

Final Thoughts

If you love the relaxing vibe of a small town, combined with historic architecture, and water views, then Chesapeake City is the perfect destination for you. Easy to explore in a day but also great for a relaxing weekend getaway, I hope you'll enjoy visiting this charming Maryland town.


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5 Great Reasons to Visit Chesapeake City on beckyexploring.com
5 Great Reasons to Visit Chesapeake City, MD
  • Chesapeake City looks like a place I’d enjoy exploring. Just love small towns and learning about their history, even better when the old buildings are still intact. I would have to take a cruise along the C&D Canal as well as try some waterfront dining!

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