Chesapeake City is a 19th-century village that, from outside appearances, hasn’t changed all that much. It began as a rough-and-tumble shipping port in 1839 when the colonial farming community “Bohemia Village” was renamed a city after the Chesapeake and Delaware Canal was built.

The town never quite lived up to “city” expectations, but hung on to a lot of the original buildings and is now on the National Register of Historic Places.

The city was split in two when the C & D Canal was built, creating north and south Chesapeake City with a draw bridge connecting the two sides. Over the years, the canal was widened and deepened for cargo ships. A new bridge was constructed in 1949 when a tanker smacked into the old bridge. And over the years the two sections took on different vibes.

And now, it’s a must-stop for recreational boaters traveling the Chesapeake Bay or going to the Delaware Bay and the northeast coast of the U.S.

South Chesapeake City

What to Do in Historic Chesapeake City

South Chesapeake City is the main village with historic buildings. That’s where you’ll find City Hall and downtown merchants.

The general store and other such shops are now boutiques, artist galleries, and antique stores that cater to tourists.

The main street, Bohemia Avenue, starts at the canal and the shops go about three short blocks up to City Hall. There are shops scattered elsewhere around the historic area.

Chesaspeake City shops

The residential area surrounds the business district for about two blocks on three sides of the district. It’s a mix of clapboard houses, some small Victorians, and a few merchant mansions. Many of them are B&Bs.

Most of the homes have been restored and colorfully painted, making for a pleasant stroll for historic house gazing. Some homes are a bit down on their luck and awaiting a new rehab, but not many.

Pell Gardens is one of the prettiest town parks in the Chesapeake Bay region. It overlooks the canal. A section of the black metal fence was the railing of the bridge that once crossed the canal.

Pell Garden in Chesapeake City, MD

The town has put together a “walking tour” map, but it just points you to all the local shops and is not a tour. You’ll come across some metal plaques as you walk about town that explains the history of the buildings.

You can set up a walking tour by one of the locals if you call ahead, and the town has a well-known ghost tour on the last weekend of every October. (Call 410-885-2415 for tour information.)

The village has a couple of large restaurants that are favorites of boaters and smaller chef-based establishments.

The granddaddy of the large restaurants is the Bayard House Restaurant (11 Bohemia Ave., Chesapeake City, MD 21915) located next to the canal. It’s a former tavern and inn and is believed to be the oldest building in town. It was restored in 1983 and has a slightly shabby kind of elegance, attracting a more mature crowd.

Upstairs, you’ll find a restaurant overlooking the canal. Downstairs is the “Hole in the Wall Bar.” Not because it’s divvy, but because there was a hole in the back of the bar when it was the Harriot Hotel in 1911. African-Americans would reach through the hole for a drink because they weren’t allowed inside.

Outside Chesapeake City’s Historic District

A couple of blocks down the waterfront from the historic district is Chesapeake Inn (605 2nd St., Chesapeake City). The restaurant specializes in seafood and has a large outdoor seating area on the deck overlooking the water.

It’s also a popular boating stop with its large tiki bar and colorful signs. They feature live music on the weekends and specialize in orange crushes and rum drinks.

Chesapeake Inn also has a no-frills marina, used mainly as a stop-over to dine and party on the deck. You’ll be able to get ice and t-shirts/hats, but not much in the way of other supplies.

There’s no grocery or convenience store anywhere within walking or easy cycling distance. Some of the downtown shops have limited drinks and snacks.

Both the Bayard House and Chesapeake Inn are great places to sit and watch the enormous ocean-faring cargo ships go by on the Canal. It’s an impressive sight.

About a mile outside of the city center is the Army Corps of Engineers’ headquarters that oversees the C & D Canal. They also run the C & D Canal Museum (815 Bethel Road, Chesapeake City, MD 21915).

It’s walkable if you have about 20-minutes to get there. Continue down 2nd Street, past the Chesapeake Inn, and circle around Back Creek (the harbor). If you prefer to drive, there’s museum parking inside and a small lot outside mainly for the boat ramp. There’s limited parking near this and it gets crowded on the weekends.

The museum tells the story of the canal’s creation and has the massive waterwheel and steam engines that filled the locks that raised and lowered the boats. Those locks have been removed as the Corp enlarged and restructured the canal.

Outside the museum is a replica of the lighthouses that lined the canal. Since it’s a Corps of Engineers museum it’s only open during weekday business hours — Monday-Friday, 9am – 5pm.

The view from the bridge is spectacular. It is possible to walk across the bridge. Doable, but not easy. There are staircases on both sides with a six-flight hike to get to the top.

The sidewalk on the bridge is about a foot higher than the road, and it’s narrow. Cars whiz by closely and large trucks make the bridge shake. If you want to cycle across, be aware that the vehicle lanes are also narrow and there are no shoulders.

There’s parking under the bridge by the steps.

North Chesapeake City

This side of town is more modern and mainly residential. It’s best known for Schaefer’s Restaurant and Canal Bar (208 Bank Street, Chesapeake City), a huge restaurant and outdoor bar on the canal that specializes in seafood.

The Canal Bar is an outside circular bar along the lines of a modern tiki bar. The open deck has cushioned Cubana lounge chairs. They also have live music on the weekends.

Schaffers restaurant in North Chesapeake City, MD

If you’re coming by boat, Schaefer’s has a bulkhead for short-term dining, a marina for overnight stays, and a fuel dock with a marine store that has boat supplies.

Next to Schaefers is the Ben Cardin Recreational Trail. It’s the Maryland end of a new trail (in 2015) connecting the Mike Castle Trail in Delaware. Together they become a 17-mile (one way), paved run/walk/bike trail from Chesapeake City to Delaware City.

The parking lot is a few blocks away off of Biddle Street, but it’s also overflow for Schaefer’s Canal House.

There are also other nearby Chesapeake City cycling trails. The highways in that area have wide shoulders and gently rolling hills, making it a great cycling region.

A note for boaters: the town has free 24-hour docking between Chesapeake Inn and the city park. There is a charge for water and electricity. You pay at the nearby city hall.

You can catch a ride between Chesapeake City’s North and South sides on Chesapeake City Ferry from April through October. The service for bicyclists and pedestrians runs Thursday through Sunday. It also offers canal tours and assorted types of boat rides through the canal.

Other Things to Do Near Chesapeake City

Mount Harmon in Maryland
Photo courtesy Mount Harmon Plantation

Mount Harmon Plantation, Earleville (600 Mt Harmon Rd, Earleville, MD 21919)

A restored tobacco plantation dating from 1651. They offer guided tours of the house and self-guided tours of the nature trails. Open Tuesday and Thursday, 10am to 3pm, Sunday 1pm to 4pm. They also have special events throughout the year. Check their website for a calendar of seasonal events.