Chesapeake City

Enjoy big-time charm in this small-time town.

Strung like a collection of gems along a necklace of green fields and the blue waters of the Chesapeake Bay, most of the historic towns and quaint villages of Maryland’s Eastern Shore are less than three hours away from the Main Line. All are filled with antique treasures, unique boutiques, charming cafés and inns, market stands bursting with local produce, and museums and marinas large and small. 

From Left: The Bayard House on the C&D Canal; an aerial view of Chesapeake City; a charming home.

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Set along one of the busiest shipping canals in the world, Chesapeake City has roots in the early 1800s, when the 17-mile canal was built to allow ships to pass from the Delaware River to the Chesapeake Bay by a quicker route. Many of the original Victorian buildings remain, used today as residences, inns and retail shops. Stop into town hall on Bohemia Avenue and pick up a map with the locations of businesses and recreational areas, which include the C&D Canal Museum

The town is split in two, with a north and a south side at either end of the canal bridge. A free water taxi runs between them April-October. The southern side has most of the shops, eateries and inns—and is entirely walkable. 

Visit and

From left: Miss Clare Cruises; Betterton Beach.

Take a narrated tour on the canal from a deadrise workboat through Miss Clare Cruises in South Chesapeake City at the city dock. Make sure you also visit the C&D Canal Museum, with its interactive displays.

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Stop in for a cool drink or a coffee and a scone at the Bohemia Café & Bakery. Other popular restaurants include the Chesapeake Inn, Schaefer’s Canal House, the Tap Room Crabhouse and Bayard House Restaurant. Most spots feature spectacular views of the canal.

Crafty ladies and gents will find a home at Vulcan’s Rest Fibers. The shop is filled with a massive selection of yarns, ribbons and threads from around the world, plus knitting and weaving patterns.

Our Best of the Main Line Elimination Ballot is open through February 22!