Chesapeake City, Maryland: A Summer Gem
Image Courtesy of Chesapeake City Chamber of Commerce
I like to think of Maryland as the South's charming cousin - nestled below the Mason-Dixon Line but still brimming with quaint allure. Along the Chesapeake Bay and Delaware Canal, Chesapeake City is a lovely historic town perfect for a summer getaway. Despite being less than a square mile, this town is filled with charm, historic inns, unique shops, and a bustling marina. Known as the only town in Maryland situated on a working commercial canal, Chesapeake City’s 19th-century architecture remains largely intact, and its south bank is listed on the National Register of Historic Places.
As early as the 17th century, local settlers, including the renowned surveyor and map maker Augustine Herman, saw the potential of connecting the Chesapeake Bay with the Delaware River. This vision became a reality, making Chesapeake City a significant point on one of the busiest canals in the world.
Chesapeake Inn Marina and Restaurant
Image Courtesy of Chesapeake Inn
One of my favorite spots in town is the Chesapeake Inn Marina and Restaurant. This venue offers the best of both upstairs dining and a downstairs casual Tiki bar experience on the water. Upstairs, you’ll find exquisite dishes, including the freshest local catches and delicious Oysters Rockefeller. Downstairs, the marina bar offers a laid-back atmosphere with equally delightful eats. This popular spot gets quite busy at sunset during the summer, so arrive early to enjoy the view. Boaters will love the Chesapeake Inn Marina, with expert marina staff, accessible amenities, and floating docks, it’s an ideal destination for a day on the water or an overnight stay. The berth is free before 11 pm, and if the marina is full, you can anchor in the adjacent Back Creek basin and use the complimentary water taxi service.
Canal Creamery and Sweet Shop
Another must-visit is the Canal Creamery and Sweet Shop. This adorable, bright historic building sits right on the water, offering a perfect spot to enjoy delicious ice cream while watching boats pass by. Occasionally, you might even catch a glimpse of an enormous container ship navigating through the canal. The picnic benches outside provide a relaxing place to sit and soak in the charm of Chesapeake City.
The Bayard House
For another dining option, head to the Bayard House. This restaurant and bar is situated on the water and offers stunning views and a cozy atmosphere. Enjoy a meal on the deck or a drink at the bar while taking in the serene waterfront views.
Image Courtesy of Chateau Bu-De Winery and Vineyard
Ship Watch Inn
For those looking to extend their stay, the Ship Watch Inn offers convenient and comfortable lodging options with beautiful canal views. This charming inn provides a perfect base to explore all that Chesapeake City has to offer.
Chateau Bu-De Winery and Vineyard
Just a short drive from Chesapeake City, the Chateau Bu-De Winery and Vineyard offers an exceptional wine tasting experience. Enjoy a glass or bottle of their exquisite wines while taking in the beautiful views of the Bohemia River. It's a perfect spot for a relaxing afternoon or a special event. For event inquiries, contact Brenda at brenda@chateaubude.com.
A Tiny, Historic Gem
Chesapeake City may be small, but it’s packed with historic charm and modern amenities. Whether you’re looking for a sweet spot to stop over or a tiny historic town for a getaway, this town has it all. From its significant 17th-century origins to its vibrant present-day attractions, Chesapeake City is a unique destination that captures the essence of life along the canal. So, pack your bags and prepare to explore the beauty and charm of this delightful town on your next summer adventure.