This quaint little town, previously named Village of Bohemia or Bohemia Manor by Augustine Herman a Bohemian explorer, cartographer and merchant born in 1621 in The Kingdom of Bohemia, today known as Czech Republic also knows as Czechia. 

Chesapeake became the new name after C&D Canal (Chesapeake and Delaware Canal) in 1839 and it is the only town in Maryland situated along an active commercial canal that happens to be one of the busiest canals in the world.  Part of the town is beneath a bridge.   Because the canal was built in the middle of the town, the town was split into two sections, north and south and connected by a drawbridge until the bridge was destroyed in 1942.

By 1911 a small community of Ukranians purchased farmland and established homes on the edge of Chesapeake City.  During the late 20th century, Chesapeake City was recognized as the most important thoroughbred stud farms in the world, the Winfield’s Farm.  By the 1920s, Ukrainans brought their culture and traditions to the top of Maryland’s Eastern Shore.   They also established Ukranian Catholic Churches and Orphanage along the canal, operating until 1970s, however the Church is currently active in serving the community with regular services.  

The new current bridge is called the Chesapeake City Bridge and was opened in 1949 and carries Route 213.  The bridge is long and very tall for large equipment and vessels to pass  underneath.  The new bridge is almost identical the St. Georges Bridge in Delaware.  Unfortunately, this new modern bridge stole much of the towns traffic to cross into the city and for many decades businesses declined.  

Chesapeake City is a water community, where you can enjoy live music events in the summer, great restaurants, many bed and breakfasts, a tiny playground for the kids, small shops and a destination to park your boat and walk around town for the day.  This town is very welcoming and the overall environment feels relaxed.

As of 2026, its growing population is 752 and Chesapeake City is listed not The National Register of Historic Places in 1966 and the South Chesapeake City Historic District was also listed in 1974.