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Quintessential Chesapeake Bay Towns

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Annapolis Waterfront
Annapolis Waterfront
Colorful Houses Susquehanna Waterfront
Chesapeake City
Photo By: Clark Vandergrift
Fells Point
Fells Point

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. 

Baltimore has the foodie experience for you, whether it's Mezze's Mediterranean-inspired menu, local seafood or bombastic burgers and beer. Photo By: Clark Vandergrift

1 Baltimore

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 Photo By: Annapolis Arts District

2 Annapolis

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 Photo By: B. Peters

3 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. Photo By: Maryland Office of Tourism

4 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 Photo By: Sabrina Raymond

5 St. Michaels

Nestled along the Miles River, this chic historic waterfront town is home to museums and boutiques, gourmet restaurants and crab houses. Bustling with plenty of opportunities to get out on the water with private boat tour companies 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 Photo By: Sam Kittner/kittner.co

6 Cambridge

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 Photo By: Red Eye's Dock Bar

7 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

Chestertown

Kent Narrows

North East

Chesapeake City

Plein Air Painting in Leonardtown Photo By: St. Mary's County

8 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:

Galesville

St. Mary's City

Leonardtown

Crisfield

Easton

Chesapeake Bay Sunset

9 More About the Great Chesapeake Bay Loop

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Travel Around the Chesapeake Bay Loop

Experiences Along the Great Chesapeake Bay Loop

Stay Along the Great Chesapeake Bay Loop

Trip Suggestions for the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

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