Historic Towns of the Chesapeake Bay

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Dock St, Annapolis, MD 21401, United States

On many go-to travel lists, Annapolis contains more colonial mansions, original historic buildings than any other Maryland town. And, the scenic downtown is a hotspot with stylish boutiques, casual bars & trendy restaurants.



3 3rd Ave, Betterton, MD 21610, United States

This town used to be a major resort town on the Chesapeake Bay. Now, it's a tiny town far out in the country with a big beach that has amazing views of the Bay. Well worth a trip if you like to explore.



200 Byrne St, Cambridge, MD 21613, United States

This is the birthplace of Civil War activist Harriet Tubman. It has two modern waterfront parks while the town has maintained its cool, 1950/60's retro-downtown that's being revitalized with hip restaurants, a brewery, boutiques and antique shops


Chesapeake City

108 Bohemia Avenue, Chesapeake City, MD 21915, United States

Popular on Top Ten travels lists, Chesapeake City is on the canal between Chesapeake Bay and Delaware Bay. Much of the historic village has been restored to it's turn-of-the century look. Huge cargo ships along with luxury yachts continually motor by the downtown making a very impressive view.



118 N Cross St, Chestertown, MD 21620, United States

Chesapeake Bay towns don't get much more quaint than Chestertown. This county-seat has colonial mansions on the river, a town square with a huge Victorian fountain, a colony of semi-retired artists and festivals throughout the Spring, Summer and Fall.



319 W Main St, Crisfield, MD 21817, United States

This is the jump-off point to Tangier and Smith islands, but it's also a down-and-out former oyster canning town with one of the best sunsets you'll see on the Chesapeake Bay. The town is also known for it's rockin; festivals



533 Deale Beach Road, Deale, MD 20751, United States

Deal is a modern fishing village with waterfront bars/restaurants on the Chesapeake Bay. They cater mainly to boaters, but they're a great place to be waterfront if you don't have a boat.



14 S Harrison St, Easton, MD 21601, United States

Historic Easton is a unique mix of uber-wealthy waterfront mansion owners, and earthy watermen. Both are often hunters throughout the region. There are fashion boutiques near the downtown gun shop. They have gourmet restaurants and down-home cooking cafes. It's not on the water, but it's the center of water-life on the Eastern shore.



100 Railroad Avenue, Elkton, MD 21921

Elkton is the county seat at the start of the Elk River. There's not much to see there unless you're doing county business.


Fredericktown & Galena

101 N Main St, Galena, MD 21635, United States

Fredericktown was nearly destroyed in the War of 1812 and as a result nearby Galena is now the "big" village. It's a popular boaters stop at the top of the beautiful Sassafras River.



988 Main St, Galesville, MD 20765, United States

A sleepy waterfront village with popular waterfront bars/restaurants. A good place to go for dining on the water.


Havre de Grace

711 Pennington Ave, Havre de Grace, MD 21078, United States

Havre de Grace is a popular getaway village for boaters & Baltimore residents. It has antique shops, boutiques and fun bars/restaurants. The downtown area is up a bit from the Chesapeake Bay entrance but still a great vista from certain places.


Kent Island/Stevensville

Stevensville, MD, United States

Kent Island has some of the prettiest Chesapeake Bay beaches and the biggest crab houses/dock bars. The old village of Stevensville is a cross-roads full of antique shops with a nice historic walking tour.


North Beach

8916 Chesapeake Avenue, North Beach, MD 20714, United States

North Beach is like a mini-version of a Maryland, Delaware or New Jersey shore town plunked on the Chesapeake Bay. It has a large city beach and a small collection of the standard beach shops.


North East

106 S Main St, North East, MD 21901, United States

North East looks like a cute, historic beach town of all of three blocks, but there's no beach in town exactly. It's on the start of the North East River. Good place for a antiquing or weekend getaway.



101 Market St, Oxford, MD 21654, United States

Oxford is about the prettiest town on the Chesapeake Bay, full of little houses with white-picket fences, a real Colonial inn and a water ferry. It has a couple beautiful town beaches and is known for it's homemade ice creamery.


Poplar Island

38.77370902900856, -76.37967824935913

Poplar Island is currently being rebuilt using bottom land dredged from the Chesapeake Bay. The state is building a nature preserve and they offer tours. It's a fascinating trip that leaves from just outside Tilghman Island.


Rock Hall

5585 Main Street, Rock Hall, MD, United States

Downtown Rock Hall is all of two blocks long with a quaint, old-timey ice cream shop, a well-used regional music hall and a few stores. But get there on a festival weekend and the tiny town is rockin'. Aside from festivals, it's best known for two big crab-house/dock-bars and a couple small, gourmet restaurants.


Smith Island

20846 Caleb Jones Rd, Ewell, MD 21824, United States

This is the original home of Smith Island cakes. But the island is a time-warp away from the rest of the U.S. The islanders speak a unique style of English and most families still make their living off the water.


Solomon's Island

14175 Solomons Island Rd S, Solomons, MD 20688

Solomons, also called Solomons Island, is an town of about 2,300 where the Patuxent River flows in the Chesapeake Bay. During the summer, the population can go as high as 15,000 as boaters fill the huge marinas. There is no beach, but there are big waterfront bars that are hugely popular.


St Mary's City

18751 Hogaboom Lane, St Mary's City, MD, United States

St. Mary's City is the most intact 17th century English town in the U.S. It's been recreated as it was, using the foundations located under a farm field. St. Mary's City was also Maryland's first capitol, when the state was a colony.


St. Michaels

300 Mill St, St Michaels, MD 21663, United States

St. Michaels is a great weekend escape location. It has numerous restaurants, boutiques, spas, antique stores and a huge maritime museum. There's also a winery, brewery and distillery. Plenty of interesting day-tripping places nearby. The highways have wide shoulders for excellent cycling. And the town has a lively nightlife.


Tangier Island

16215 Main Ridge Rd, Tangier, VA 23440

Tangier Island is a lot like Smith Island, but it's on the Virginia end of the Chesapeake Bay. This is where you go to get a real Chesapeake Bay crab cakes. It also has an amazing, pristine white-sand beach. You can get there only by boat.


Tilghman Island

5949 Tilghman Island Rd Tilghman Is MD 21671

Tilghman Island is where you for a slow trip with easy exploring and beautiful places to read a book. Hollywood celebrities occasionally go there to escape and not be seen.


Tolchester Beach

21085 Tolchester Beach Rd, Chestertown, MD 21620, United States

Tolchester was a turn-of-the-century resort town where Victorians would spend the weekend. Today, it's a marina with a big, rockin' Tiki Bar on a sandy beach.


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