8 of the Most Hospitable Small Towns in Maryland

Maryland, nicknamed the Old Line State, might seem like a place stuck in the past. However, it contains several small towns rapidly growing with families, college students, tourists, and/or modern businesses. But, because they have not yet become big cities, they have retained their heritage, friendliness, peacefulness, and, in many cases, affordability. All of these traits combine to create very hospitable haunts. Here are eight such small towns in Maryland with old-line charm but new-line development.

Berlin

There is no wall around Berlin, Maryland. In fact, its population has doubled since the town underwent a revitalization project in the 1980s. Proactive politicians and private citizens built Berlin into a national historic site mixed with hip businesses. In 2014, this Eastern Shore oasis was voted "America's Coolest Small Town" by readers of Budget Travel. Today, Berlin is home to 47 National Historic Places, over 60 shops, 15-plus restaurants, and 32 flavors at the famous Island Creamery. It is also home to just over 5,000 presumably chill and happy people. Berlin is liable to double again in the next decade. Visit before it loses its small-town status.

Chestertown

Another Eastern Shore success story, Chestertown went from having around 3,000 residents in the 1980s to nearly 6,000 today. It combines the charm and heritage of a small town with the vibrancy and openness of a big city. The latter qualities are due to Washington College, a private liberal arts university attended by George Washington and located in Chestertown's historic area. The college supplies Chestertown with hundreds of new residents and perspectives, while Chestertown supplies the students with one of the most beautiful downtowns with some of the best shopping and entertainment in rural America. On the first Friday of every month is First Friday, a longstanding tradition where townsfolk and tourists patronize spectacular shops and restaurants like Walnut & Wool and Stam's Luncheonette, while the Chestertown Tea Party Festival happens each Memorial Day weekend and commemorates the town's role in the American Revolution.

Brunswick

West of the Chesapeake Bay is the small "city" of Brunswick, which definitely deserves a peek. Home to around 8,000 people and counting, this former forgotten haunt in the boonies has undergone revitalization and is now a thriving and accepting community. Potomac Street Grill, Beans in the Belfry, and Smoketown Brewing Station are just some of the businesses bringing new life to Brunswick. Old life is preserved by historic parks like Gathland on the Maryland side of the Potomac River and Harpers Ferry on the West Virginia side. Housing prices are still low, so you can also have a cheap life in Brunswick.

Sykesville

This ville is one of the least hospitable places in Maryland. Syke! Sykesville was the 2016 winner of Budget Travel's Coolest Small Town in America contest and the 2020 winner of Independent We Stand's Best Main Street in America contest. The coolest sites on Main Street include E W Beck's Restaurant & Pub, Sykesville Town House, Sykesville Art and Wine Festival, and a farmers' market that runs every Sunday from May through October. Off Main Street, Sykesville has affordable homes, highly rated schools, and racially and politically diverse residents. It is one of the most welcoming towns in Carroll County.

Kensington

Kensington is a town with just over 2,000 residents in the Washington, DC, metro area. As such, it is a quaint, laid-back enclave of perhaps the most powerful region in the world. Its one-half square mile of land contains historic buildings like Kensington Town Hall, annual events like Kensington Day of the Book Festival, a weekly farmers' market, and beautiful, spacious homes, making it a hotspot for families with small children. Appropriately, the Latter-day Saints' Washington DC Temple, whose spires loom over Kensington, is often mistaken by kids for Disneyland. Kensington may not be the happiest place on Earth, but it is one of the happiest towns in Maryland - for a price.

Leonardtown

If you thought Berlin's and Chestertown's growths were impressive, wait till you hear about Leonardtown's. This Southern Maryland community had roughly 1,500 people in the early 1990s. Today, it is approaching 5,000. The reasons are clear: Leonardtown has a disproportionate amount of activities for its size. Seaplane rides, boat cruises, trolley tours, art workshops, kayaking, wine tasting, axe throwing, a butterfly trail, an old jail visit, billiards, golf, yoga, and even floating sound baths are offered in or around the little town. Its restaurants deserve special mention. They include The Front Porch, Social Coffeehouse & Cocktail Bar, The Slice House, IL Piccolo Morso, Happy Dragon Restaurant, and Brüdergarten, among many others. There is something for everyone in Leonardtown.

Chesapeake City

Chesapeake City is, ironically, not a city and not on the Chesapeake Bay. It is a town a few miles from the Bay on the Chesapeake & Delaware Canal. Being the only town in Maryland on a working commercial canal, Chesapeake City might conjure images of a hectic industrial hub. Instead, it is one of the calmest and prettiest communities in the state. Visitors walk the scenic, canal-straddling streets, stopping for ice cream at Canal Creamery and Sweet Shoppe, coffee at Cafe on the Bay, or a tour of C & D Canal Museum. But Chesapeake City is not a tourist trap. It is home to over 700 permanent residents, many of whom live in vibrant and affordable houses. One downside is that they have to drive for groceries. Luckily, Elkton, a larger and similarly scenic town, is less than ten minutes away.

St. Michaels

Seventy miles south of Chesapeake City is St. Michaels, a town with just over 1,000 people on the Miles River. Since this river runs into the Chesapeake Bay, the town's main attractions surround seafaring. Chesapeake Bay Maritime Museum is an 18-acre preserve of Navy Point, a former coastal hub full of everything from docks to ships to seafood packing plants. Seafood is still abundant in town. Visitors can dine on fresh oysters at Ruse and crabs at The Crab Claw. They can even wash it all down with a bottle of rum from Lyon Rum // Windon Distilling. It is a pirate's life in St. Michaels but without all the crime.

Rural Maryland is not a dead end. As proven by Berlin, Chestertown, Brunswick, Sykesville, Kensington, Leonardtown, Chesapeake City, and St. Michaels, the Old Line State is in a state of new growth in many rural areas. Yet the growth is not so rapid as to have stripped these small towns of their charm and friendliness. If anything, it has made them even more hospitable. Go check them out for yourselves.