7 Towns In Maryland With The Best Downtown Areas In 2024

A seasoned vacationer will tell you that a town is as good as its downtown area. It does not matter if it has the best theme park in the world, a rich history, or a kick-ass dining scene. Maryland, one of the original thirteen colonies, is start-studded with an enchanting range of many beautiful towns, some of whose downtown areas look plucked straight out of a movie scene. Granted, many will cast their vote for Fredrick, a dreamy place that looks like a well-planned neighborhood more than it does a city. But the focus here is on slightly smaller towns. Here we go.

Annapolis

Transport your mind to charm-soaked streets, a quaint, historic waterfront, and a couple of 300-year-old buildings. Speaking of years, Annapolis was settled in 1649. Its settlement history, therefore, goes back more than 370 years. Start exploring Annapolis at the top of Main Street, preferably after a hearty breakfast at Miss Shirley's Cafe, whose dishes — which should feature blueberry pancakes — come with lots of yummy twists. Walk down the hill, taking it slow and light, until you reach City Dock, where you can relax on a bench that overlooks the beautiful harbor. One can easily lose all sense of time here, as the sumptuous views, sprinkled with the sight of cruising boats, can put one in a dreamy, trance-like state. Have a glimpse of the Maryland Statehouse, which is open to the public every day from 9.00 AM to 5.00 PM. We are talking about the oldest state capitol in continuous legislative use in the entire nation and the only one to have served as the nation's capital.

Westminster

Westminster has some interesting claims to fame, including being the site of the first rural free mail delivery in the United States. It was founded in 1764 and initially named Winchester after the founder. A frustrating confusion with Winchester, Virginia, however, forced the town's early settlers to rename the town for London's Westminster borough. A summer afternoon stroll can reveal much about Westminster’s downtown beauty. Westminster is a suburb of Baltimore, only about 30 miles stand between them. It boasts some really great restaurants, including Rafael's, Rock Salt, and O'Lordan's, which is set in a beautiful 19th-century stone building. The town's Main Street, with its beautiful shops and boutiques, is usually the main draw.

Carroll Arts Center, which locals love to bits, is a shining beacon of culture and community. With academic institutions such as the McDaniel College, the ambiance here is open, warm, and vibrant. Just don't miss Hoffman's Ice Cream, which serves the best homemade ice cream for miles.

Berlin

Although Paris is known across the globe for its alluring thrifting scene, Berlin, a cute little town in Maryland, can make one for a moment think she is in the City of Light. Open Hand Thrift, for example, just outside Main Street, has almost everything, whether kitchenware or jewelry. But the inner core, with its tree-lined streets and Victorian charm, can also steal the show. No wonder Berlin's downtown is a National Register Historic District — and has served as the setting for many films, including Tuck Everlasting, an American romantic fantasy drama film that was released in 2002. With its many galleries and murals, Berlin’s art scene is not just alive but thriving. The Worcester County Arts Council, right in the heart of town, features unique, hand-crafted artwork, mostly from local artists. There is also Calvin B. Taylor House, an eye-catching Federal-style house that serves as a repository of local history. For something off-the-beaten-path, look no further than the Mermaid Museum. It is a fun, quirky distraction with a lot of information about the history of mermaids. Xxx

St. Michaels

Unless you have had the pleasure of experiencing it, you may find it hard to believe that St. Michaels has the most endearing Christmastime Main Street, not just in Maryland but also in the entire country. Granted, it is still magical January and June, but when the festive season knocks, it takes everything a notch higher. That said, its year-round features include kitschy nautical shops, a beautiful waterfront, cobblestones, historic homes, and a swoon-worthy setting on the Chesapeake Bay. The Wildset Hotel, with its eye-catching swimmers mural, has a history that dates back to the 19th century. Chesapeake Bay Maritime Museum offers a glimpse into the misty past — as is the Hooper Strait Lighthouse, loved for its interesting maritime artifacts and stories. But time also seems to stop along Talbot Street, a lovely stretch that almost looks like it did 50 years ago.

Catonsville

Although they are close to each other, don't ever be tempted to overlook Catonsville for Ellicott City, a mistake that many make. The truth is, Catonsville is a hidden gem — and that is knowing the phrase is often misused. This Maryland treasure is cool, charming, and highly walkable. It boasts a lot of cute shops and restaurants so that a downtown adventurer will not be spoilt for choice. The bare minimum of a good Downtown area can be a long list of items. A good toy store, however, should never miss out on the list. Better World Imaginarium, which is small but well-curated, is just such a place. Walking down Frederick Road, with its trees and beautiful architecture, can feel like strolling through a Norman Rockwell canvas. There is the Lurman Woodland Theater if one wants to catch a good show — and Patapsco State Park — for those who want to venture out into the Great outdoors.

Havre de Grace

Think of Annapolis but without the crowds. That is one of the best descriptions of Havre de Grace, a quiet and picturesque Maryland gem that reclines at the mouth of the Susquehanna River on the beautiful Chesapeake Bay. Expect gorgeous waterfront views, colorful murals, and a charming, revitalized downtown. Stroll through Harmer's Town Art Center's mural park, for instance, and chat with local artists as you admire their beautiful exhibits. Linger a bit at the still brand new Graw Alley Public Art Park, a living and evocative outdoor art space dedicated to teaching the history of the town. If into lighthouses, perhaps because of what they embody, Concord Point Lighthouse is just a heartbeat away. Just don't miss a stroll along the boardwalk.

Leonardtown

Leonardtown has a cool little downtown area, the only designated Arts and Entertainment district in Southern Maryland. It spots breathtaking waterways, beautiful streets and landscapes, and a delightful range of pleasure spots. The Old Jail Museum, which looks like a time capsule, retains its original upstairs cells where convicted prisoners were once segregated by gender and race. The Leonardtown Visitor Center, also at the site, can help with mapping out one’s itinerary and maxing out on the experience. A traditional breakfast at Ye Olde Towne Cafe, some sweet treats at Heritage Chocolates, and Port of Leonardtown Winery, the first of its kind in the county, should all feature on one's itinerary.

The Takeaway

Maryland is known for many things, including its rich and storied history. The home state of Edgar Allan Poe was among the original thirteen colonies. Many of its towns are old, predating American Independence by several decades. Annapolis, for example, was already a proper town when the delegates signed the Articles of Confederation. Yet some of these towns are not just old. They are also incredibly beautiful, with downtown areas that are charming, quaint, and beautifully preserved. These include gems such as Annapolis, Leonardtown, and Berlin.