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The 11 Most Charming Towns in Maryland

Maryland has been nicknamed “America in Miniature” for a reason. Diverse both in terms of population and landscapes, it’s a state filled with exciting things to discover. Admire the Appalachian panoramas in green Maryland’s west, try the iconic crab cake in the quaint fishing towns along the Chesapeake Bay, feel the cultural beat at the cities of the Capital Region, and embrace the Atlantic grandeur in the Eastern Shore.

Your visit to the Old Line State will be full of history too, as there are numerous Civil War-era battlefields, a kaleidoscope of museums, and plenty of old architecture. These are the most charming towns in Maryland to choose for your next getaway.

Ocean City Ocean City
Credit: Ocean City by m01229 via Flickr.com

Ocean City

It’s impossible to beat the charms of being next to the ocean. You’re lucky in Maryland, as Ocean City is a fantastic beach destination for an Atlantic break. With more than 10 miles of sandy beaches, an epic boardwalk, an endless supply of seafood joints, and plenty of family amusement, this Eastern Shore town is an absolute must. The great thing about Ocean City is that you can have different kinds of oceanside leisure here. Fancy action-packed entertainment? Jolly Roger at the Pier, Ripley’s Believe It or Not!, and Baja Amusements will supply top-notch family fun. Those who’d like a calmer beach experience will find it in the northern sections of the city. And don’t miss the sunsets; they are spectacular here.

Annapolis Annapolis, Maryland
Credit: Annapolis, Maryland by © Sean Pavone | Dreamstime.com

Annapolis

The picturesque Annapolis is a well-known charmer. Once a temporary capital of the U.S., the city embraces the waters of Chesapeake Bay and offers one of the most wholesome historic cores in the country. Stroll down the cobblestone streets, take photos of the boat-filled harbor, and get transported back in time to the 1772-built Maryland State House. Annapolis is also often named the “naval capital of the US” for being home to the United States Naval Academy (which you can visit on a tour). And no visit to the city is complete without tasting the crab cakes, and the harborside eateries will be happy to sell you some. Finish the day by greeting the sunset from the deck of a boat on a sailing tour.

St. Mary's City St. Mary's City
Credit: St. Mary's City by Acroterion via Wikimedia Commons

St. Mary's City

Discover the origins of the state at St. Mary’s City. One of the most charming towns in Maryland, it’s also its first European settlement and capital. Today the whole city is the site of a historic park with thoroughly reconstructed buildings and an unparalleled Old World atmosphere. See the 1667-constructed St. Mary’s City Brick Chapel and the original Maryland Statehouse, visit the 400-year-old trading ship called the Dove, and enjoy long panoramic walks next to the peaceful St. Mary’s River.

Cumberland Cumberland
Credit: Cumberland by wmsr.com

Cumberland

Heart of Western Maryland, Cumberland has several awesome attractions to offer. Start with exploring the historic local Downtown boasting pedestrianized streets, colorful cafes, and pretty old architecture. But you can’t leave the city without hopping on the train of Western Maryland Scenic Railroad. It’s a quintessential journey that connects Cumberland with Frostburg. The steam locomotive takes you to the superb Allegheny Mountains panoramas, passes tunnels, and rides next to the iconic Chesapeake and Ohio Canal. It’s a perfect mini-adventure for the whole family and a great way to see the beauty of Western Maryland.

McHenry McHenry

McHenry

McHenry is all about Deep Creek Lake, the largest man-made water body in the state. Surrounded by the Allegheny Highlands, it’s a beautiful area perfect for any kind of outdoor recreation. If you’re coming in winter, be sure to check out Wisp Resort offering skiing, snowboarding, and snow tubing next to the lake. McHenry is an ultimate family destination with plenty of diverse accommodation choices, spectacular natural views, and a cool food scene. Also, spare some time for visiting the Deep Creek Lake State Park for hiking trails, birdwatching, kayaking, and fishing.

Frederick Frederick
Credit: Frederick by Ron Cogswell via Flickr.com

Frederick

There’s something very European in the looks of Downtown Frederick. Walking-friendly streets full of historic houses and spired churches can be easily mistaken for small towns in Austria or France. The romantic Carol Creek with the park trails is reminiscent of the small canal cities of Belgium and the Netherlands. One of the most charming towns of Maryland, Frederick is all yours to discover. Close to both Washington D.C. and Baltimore, it offers a slow travel allure that will be filled with wine tastings, cafe hopping, and gallery exploring. Be also sure to visit the interactive National Museum of Civil War Medicine, follow the Frederick Wine Trail set among the Civil War battlefields, and take your kids on a safari at Catoctin Wildlife Preserve.

Solomons Island Solomons Island, Maryland
Credit: Solomons Island, Maryland by © stockphotofan1 | Dreamstime.com

Solomons Island

It’s going to be scenic and inspiring at Solomons. One of the favorite Chesapeake Bay escapes for Baltimoreans, this destination is where you have peace and gaze at beauty next to the water. Sailing enthusiasts will be delighted to find a sprawling marina, gourmands will love the gastronomy proposition, and art lovers will have a blast visiting the Annmarie Sculpture Garden & Arts Center. Add relaxed hiking trails, plenty of spots for fishing, and a beautiful boardwalk. You’re getting an ideal Maryland waterside retreat at Solomons.

Havre de Grace Havre de Grace
Credit: Havre de Grace by David Adorno via Unsplash.com

Havre de Grace

Apart from having a mellow-sounding name, Havre de Grace is also a superb Chesapeake Bay destination and one of the most charming small towns in Maryland. Historic Concord Point Lighthouse towers over a scenic boardwalk, the sailing opportunities are unlimited, and the water views are gorgeous here. Being at the head of the largest estuary brings fine seafood cuisine, river excursions, and majestic sunsets. Decoy Museum showcases local artisans and Maritime Museum introduces you to the town’s origins.

Berlin Berlin, Maryland
Credit: Berlin, Maryland by © Harperdrewart | Dreamstime.com

Berlin

Hipsters, techno, and Brandenburg Gate are nowhere to be found in Berlin, Maryland. What is waiting for you here, though, is a small-town bliss and a cozy city center. Proximity to the Atlantic makes it a great day trip from Ocean City. Downtown is where you’d want to be while in Berlin. The vibe is relaxed, and you can spend hours on a terrace of a coffee shop, hunting for antiquities in local stores, or simply gazing at the old architecture with an ice cream in hand. The cinematic looks put the town on a movie map too. You could have seen it playing the main role in such flicks as Runaway Bride with Julia Roberts and Richard Gere as well as Tuck Everlasting led by Sissy Spacek.

Chesapeake City Chesapeake City, Maryland
Credit: Chesapeake City, Maryland by © Jon Bilous | Dreamstime.com

Chesapeake City

Chesapeake & Delaware Canal defines this charming Maryland town creating lots of recreational possibilities for the locals and visitors. Walk around the tiny historic district, have a seafood meal at one of the waterfront restaurants, and learn more about the busy waterway at the C&D Canal Museum. Cyclists will be happy to ride along the 15-mile Ben Cardin Recreational Trail that goes all the way to the Delaware River. Also, the city will be a good base for Chesapeake Wine Trail exploration. 

St. Michaels St. Michaels, Maryland
Credit: St. Michaels, Maryland by © Jon Bilous | Dreamstime.com

St. Michaels

If you would like to get closer to the water, St. Michaels is a fantastic idea for a Maryland day trip. The majority of the visitors come for Chesapeake Bay Maritime Museum, and that’s fully justifiable. 18 acres of territory, a large boat collection, 35 historic buildings, and the lovely 19th-century screw-pile Hooper Strait Lighthouse is what you’re going to see in St. Michaels. The town also has a high sunset-walking and crab-eating potential so be sure to do that too. 

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