Quintessential Chesapeake Bay Towns



Featured Places

Annapolis Waterfront
Annapolis Waterfront
Sunrise at the Susquehanna River Bridge in Havre de Grace
Sunrise at the Susquehanna River Bridge in Havre de Grace
Image Credit: andreahdg-Instagram

BaltimoreAnnapolisGalesvilleChesapeake BeachSolomonsLeonardtownSt. Mary's CityCrisfieldCambridgeEastonSt. MichaelsKent NarrowsRock HallChestertownChesapeake CityNorth EastHavre de Grace

Looking for that quintessential Chesapeake Bay town? Someplace with great seafood restaurants and a museum that puts you in touch with Chesapeake traditions? How about beautiful only-in-Maryland bayside architecture and great local shopping to bring home those memories? And of course a lighthouse or a skipjack. Oh, and those amazing Chesapeake Bay vistas and cool, waterfront breezes are a must. Well these Chesapeake Bay towns check all of the boxes. 

Picture of a Baltimore Water Taxi Image Credit: Baltimore Water Taxi


World-class museums, thriving arts and culture districts, history, nightlife, music and more make Baltimore the urban jewel of the Chesapeake Bay. Nicknamed a “Nest of Pirates” by the British, the people of Fells Point prefer the term “Privateers.” Whatever the name, Fells Point has been a hangout for sailors and travelers since the 1700s, and even today, it retains that swashbuckling attitude (Don’t believe us? Visit during the annual Privateer Festival!) just as it retains its original cobblestone streets and quaint architecture.

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Annapolis Arts District Image Credit: Annapolis Arts District


From the soaring statehouse dome topped with a lightning rod made by Benjamin Franklin, on down the old bricked streets and past mansions to the continuous boat parade in Ego Alley, visiting Annapolis is a capital idea. Be sure to cross the harbor to the Maritime Republic of Eastport and visit the Annapolis Maritime Museum in the McNasby Oyster Packing House.

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Main Street, Havre de Grace Image Credit: B. Peters

Havre de Grace

Experience the full beauty of the Susquehanna River as it flows into the top of the Chesapeake Bay from the picturesque waterfront promenade with its charming Concord Point Lighthouse. Other not-to-be-missed sites are the world-renowned Havre de Grace Decoy Museum and the downtown shopping district.

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Food tastes better by the water, and what better place for a crabfeast than in Solomons on the Chesapeake. Image Credit: Maryland Office of Tourism

Solomons Island

With breathtaking views of the Patuxent River and sunsets, this working waterfront community is a perfect mix of traditional and contemporary, served at a laid-back pace. Charter boats abound for fishing trips and the Calvert Maritime Museum is home to river otters, Drum Point Lighthouse, tour boats, a paleontology gallery and lab, and more.

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People on a boat crossing the bay to St. Michaels Image Credit: Sabrina Raymond

St. Michaels

Nestled along the Miles River, this chic historic waterfront town is home to museums and boutiques, gourmet restaurants and crab houses. There are plenty of opportunities to get out on the water with private boat tour companie or small boat rentals at the Chesapeake Bay Maritime Museum, this spirited town is also home to several wineries, breweries, and distilleries.

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Cambridge Image Credit: Sam Kittner/


Located on the broad Choptank River in the heart of the Eastern Shore, this classic-yet-contemporary town retains its rich maritime history while adding a fun, modern slant. Sail on the skipjack Nathan of Dorchester, walk in the footsteps of Harriet Tubman, and enjoy the hip culinary and art scene of downtown.

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Red Eye's Dock Bar - Kent Narrows Image Credit: Red Eye's Dock Bar

More along the Upper Loop

If you have more time to visit, check out these other towns along the upper half of the Chesapeake Bay:

Rock Hall


Kent Narrows

North East

Chesapeake City

Plein Air Painting in Leonardtown Image Credit: St. Mary's County

More along the Lower Loop

If you have more time to visit, check out these other towns along the lower half of the Chesapeake Bay:


Chesapeake Beach

St. Mary's City




Chesapeake Bay Sunset Image Credit: motoxdms-instagram-

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Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
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