Quintessential Chesapeake Bay Towns



Featured Places

Chesapeake City
Chesapeake City
Photo By: Clark Vandergrift
Main Street in Havre De Grace
Main Street in Havre De Grace
Photo By: Clark Vandergrift

Each of these Chesapeake Bay towns has all the elements that provide a not-to-forget Chesapeake Bay visit. A waterfront area to enjoy the cool breezes and lovely views. A Chesapeake heritage museum to learn about the local traditions. At least one seafood restaurant so you can get your fill of Chesapeake seafood. Local architectural styles based on the needs of the community (vernacular architecture).  Shopping so you to acquire your treasure to take home. And a lighthouse and/or a skipjack you can tour.

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 Fells Point, Baltimore

World class museums, thriving arts and culture districts, history, nightlife, music and more make Baltimore the urban jewel of Chesapeake country.

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Annapolis Arts District Photo By: Annapolis Arts District

2 Annapolis

From the soaring statehouse dome on down the old bricked main street to the mega-yachts of Ego Alley, visiting Annapolis is a capital idea!

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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 lighthouse.

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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 Solomon's 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.

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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.

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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 pop.

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Red Eye's Dock Bar - Kent Narrows Photo By: Red Eye's Dock Bar

7 More of the top half of the Bay

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

Rock Hall


Kent Narrows

North East

Chesapeake City

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

8 More of the bottom half of the Bay

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


St. Mary's City