6 Best Downtowns In Maryland
From a rich history to some unexpected treasures, Maryland has some charm and character unlike any other. This is especially so in the small towns dotting Maryland, where their simple downtowns are bursting with character, maintain their historical roots, and have businesses that are tied to the communities; the owners still greet customers by name. From historic candy shops to quaint railroad history, Maryland's rich history comes alive in these town centers. Whether you're thinking you need a day trip or a more peaceful vacation, consider traveling out to one of the following downtowns and experience something unexpected and different.
Boonsboro
Boonsboro is a small town, but its charm is big and memorable. There are a handful of low-key restaurants and local shops, but what ties everything together is the landmarks and the surrounding area.
To start, Boonsboro has a quirky museum in the Boonsboro Trolley Museum. Built out of the last remaining trolley station in Washington County, the museum has several trolley artifacts and photos. In addition, the Boonsborough Museum of History is considered one of the finest private museums in the region, often referred to as a miniature Smithsonian. It houses an extensive Civil War collection that includes some items from the Antietam and Gettysburg Campaigns. Lastly, the National Road Museum is another historic landmark that tells the story of America's first federally funded highway. The museum does a deep dive and tells this story through an extensive list of exhibits, which also includes historic images, artifacts, maps, murals, artwork, videos, photographs, and more. After a day of exploring local history, enjoy a Mexican meal at Sizzling Fajita, right down the street.
Chesapeake City
Situated on a working canal, Chesapeake City is a small town with fun activities for locals and tourists alike. Within town, the Ben Cardin C&D Canal Trail connects to Delaware's Mike Castle Trail, which stretches along the canal. The entire trail is 17 miles long and gets you to Delaware City if you like. A particularly unique store that's an absolute must for those with a sweet tooth is the Chesapeake Candy Works, a gourmet candy and luxury chocolate store. They even serve fat-free frozen yogurt. During the warmer seasons, the Chesapeake Water Tours open up with sunset cruises, private parties, corporate outings, and live music cruises available, making them flexible for everyone's needs. And if you miss the water tours, the Pell Gardens are a solid alternative. With events held during the summertime and more frequently during the winter now too, the waterfront park is beautiful any day of the year for you to relax and enjoy.
Berlin
Dubbed the "Coolest place in Maryland," Berlin certainly fought for that title. Its Main Street alone is considered one of the Top 10 Great American Main Streets, according to Main Street America. What makes it so great is extensive, but the looks and charm are some of the biggest contenders.
What sets the stage for the downtown area is the Atlantic Hotel, a landmark that's been in the town since the 1890s. Its broad porches and classic look only accentuate the brick storefronts and wide sidewalks of the downtown area. In addition, you have nearly 75 boutiques, shops, and cafés to choose from, giving you plenty of time to linger around. That said, other natural landmarks are iconic in their own way. For example, Heron Park, Berlin's newest park, a twenty-minute walk from downtown, is filled with natural assets where people can walk, run, and watch wildlife from dawn until dusk. And if you like the historical look of the Atlantic Hotel, you could swing by the Calvin B. Taylor House Museum, where the historical landmark home has turned into a museum displaying local memorabilia, a shady lawn, and other interesting displays.
St. Michaels
Shaped by shipbuilding, maritime battles, and a vibrant waterfront life, St. Michaels is a blend of rich history and scenic maritime charm. The whole downtown area is filled with coastal-inspired shops and sights, making the streets a calming experience to enjoy. You get this strong sense immediately from places like the Chesapeake Bay Maritime Museum, an expansive waterfront complex with preserved hands-on exhibits, vessels, and a view that extends to the river. Another historical landmark to check out is the Cannonball House, an architectural treasure with an interesting history involving a cannonball. Visitors can hear about the history of how this home had a cannonball lodged into its walls during the Civil War era, in addition to viewing other intriguing artifacts and informative displays. And for another hit of nostalgia, another intriguing place to check out is the Classic Motor Museum of St. Michaels, which features a truly impressive display of vintage classic cars and some rare models. The museum goes into extensive detail about the history of wheels and how these cars were built. Afterward, check out the Fool's Lantern for small plates and an excellent beer selection.
Sykesville
Sykesville offers a unique experience in its vibrant downtown. The buildings in the downtown area are all restored and are accompanied by tidy sidewalks, inviting storefronts, and natural beauty to make it worth a stop to visit, especially during the spring and summer months.
With the Patapsco River being close by, tubing down the river is a great way to spend time. People can also fish there, and there are plenty of spots to do so. In town, the S&P Railway Model Train Display offers a unique experience for viewing trains, where these model trains display historic train cars in a downtown area. In addition, the Sykesville Gate House Museum of History offers another form of rich history, with the building itself being a former hospital center. Today, it exhibits historical artifacts within the town and serves as a general archive for the town. For an elevated midday dining refresh, stop into the Kate Pearl Tea Room on Main for an elegant traditional tea service with pastries and tea sandwiches.
Cumberland
A blend of historical charm and modern flair, Cumberland is a mountainside town with beautifully preserved downtown buildings and church steeples, all framed by the Appalachian Mountains. The downtown is a hub of recreation, with the start of the Great Allegheny Passage being a must-visit. The trail travels through tunnels and across viaducts, giving people scenic views and towns across Maryland, including Cumberland. There's also the Western Maryland Scenic Railroad, which is considered to be one of the Best Scenic Train Rides in the United States, according to USA Today. The ride is a fan favorite and takes three hours to complete, giving you a look at the surrounding area, including the Allegheny Mountain range and a rest area at the historic Frostburg Depot station. And if your enthusiasm for history is about the architecture, the Emmanuel Episcopal Church is a fine example of early Gothic Revival churches. It has a lot of deep history, including the fact it was modeled after St. Paul's Church in Brighton, England.
From experiencing the vibrant culture of Berlin to getting your fill of history in Boonsboro, Cumberland, and Sykesville, Maryland's small towns have a lot to show off in different ways. Each of these communities offers a nice blend of history alongside abundant creativity and local pride that you can feel in the area. So whether you are passing through or stopping to stretch your legs, the walkable downtowns can be just the stop you need. And if you linger around for just a little longer, these places could even create a lasting impression and some unique experiences that can create some unexpected and pleasant memories.
