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Winter sunrise | © Charlie Stinchcomb/Flickr
Winter sunrise | © Charlie Stinchcomb/Flickr

The Best Spots to Visit Along Maryland's Chesapeake Bay

Picture of Jasmine Eppes
Freelance Writer
Updated: 15 February 2018

If you’re planning your next trip to Maryland, there are plenty of quaint towns along the way to the Chesapeake Bay. These small towns are not only rich in history, but have plenty of things to do and see, including catching the amazing water views. Check out some of these spots and take time to experience small-town life.


Cambridge, Maryland is a city rich in history, such as that regarding the Underground Railroad, and a haunted street. This town sits on the Choptank River and its dock is the perfect place to dock your boat. This town has a population of approximately 12,000 inhabitants who appreciate a good crab cake and living on the water.


Easton, Maryland, is the perfect little town to stop by on your way to Ocean City. It not only has quaint little restaurants, ranging from Italian cuisine to pub food, but it has a rich cultural spirit that you can’t help but enjoy. There are many small shops, along with great antique shopping for those looking to make something old into something new. The Victorian-style architecture of the town is also a sight to behold as its original state has been preserved throughout the years.

Chesapeake City

Chesapeake City, Maryland, is another town located on the Chesapeake Bay. It has Colonial-style and Victorian-style homes that are located all around the Chesapeake & Delaware Canal, that’s still being used to this day. This town has many local storefronts with unique shopping and fantastic restaurants that specialize in fresh and sustainable seafood.

Havre de Grace

Havre de Grace, Maryland, is an amazing city that has the perfect marina to dock your boat, as well as a fishing pier and lighthouse. At the lighthouse, you’re able to see amazing views of the Chesapeake Bay, and while on the fishing pier, feel free to watch the sunrise and watch birds in the fresh air. There are also great opportunities to shop and dine while visiting the promenade in the downtown historic area of Havre de Grace.