6 Quietly Charming Towns In Maryland

Maryland's small towns reflect both its layered history and its varied scenery, combining colonial history with beautiful views of the Chesapeake Bay. From the harbor views and maritime heritage of St. Michaels to the mountain scenery surrounding Oakland, these are six quietly charming towns in Maryland that reflect the state’s range of landscapes and history. What they have in common, aside from representing Maryland’s diversity, is the charm and atmosphere that come from being a coastal, Mid-Atlantic state with a maritime history and a unique place in America’s geography.

St. Michaels

St. Michaels is a seaport on the Miles River, known for its maritime history and for its stunning harbor. The Hooper Strait Lighthouse, a screw-pile structure built in 1879, is now administered by the Chesapeake Bay Maritime Museum. The museum sits on 18 acres of waterfront land and tells the story of the town’s boat-building and oystering heritage. St. Michaels has a walkable commercial district along Talbot Street, lined with red brick sidewalks and Victorian architecture. This historic thoroughfare now houses a collection of locally owned businesses, including several antiques shops, such as Antiques On Talbot, a friendly store with a vast collection of local history and Americana. As a maritime town, seafood is a big part of the local cuisine. The Crab Claw and St. Michaels Crab & Steakhouse are both popular places for Maryland blue crabs. For drinks, Lyon Rum Distillery and Eastern Shore Brewing offer tasting rooms.

For outdoor exploration, the nearby St. Michaels Nature Trail is a 1.3-mile walking and hiking trail that features a covered bridge. Boat tours depart from the harbor for historic tours of the Miles River and the waterfront estates that line the river. The nearby Tilghman Island is a fishing island, where you can watch boats bring in the daily catch. The Miles River is also popular for kayaking and exploring the coastline.

Chestertown

Chestertown is a historic town on the eastern shore. It is known for its colonial architecture and annual festivals. On the Chester River, the town’s historic waterfront is famed for its well-preserved 18th-century architecture. Contemporary Chestertown is also renowned for its vibrant arts scene. The designated Arts and Entertainment District includes the Garfield Center for the Arts and several local galleries. The Historic District contains Maryland's second-largest collection of restored 18th-century homes.

A key event in the town’s cultural calendar is the Chestertown Tea Party Festival, taking place every May. It features colonial re-enactments to honor the town’s 1774 Tea Party, when residents tossed British tea into the river. The festival includes over 100 vendors and a Beerfest at Wilmer Park. Other festivals include the Chestertown Jazz Festival, which takes place annually on the riverfront, and Paint the Town, an annual four-day plein-air event. Just a short walk from downtown is Washington College, one of the oldest liberal arts colleges in the US, with a vast campus. For some outdoor activities, the Chester River Water Trail is a 46-mile trail for boating and kayaking on the Chester River and its tributaries.

Chesapeake City

Chesapeake City is a lovely town known for its canal. The town is split into two sections, North and South, by the Chesapeake & Delaware Canal. This 14-mile-long, 450-foot-wide, and 35-foot-deep ship canal connects the Delaware River with the Chesapeake Bay, at the border of Maryland and Delaware. There is a ferry service from April to October that connects the North and South sides of the canal. Crossing is also possible with the 140-foot-tall Chesapeake City Bridge. Along the water, the C&D Canal Museum is on the South Side and features a large waterwheel and the steam engines that once operated the original canal locks.

The town is celebrated for its well-preserved 19th-century architecture and is listed on the National Register of Historic Places. The main street in its South Historic District is Bohemia Avenue. Here you will find boutiques, antique shops, and restaurants. Canal-side dining is a big draw, where you can watch massive ocean-going vessels passing by. For food, Chesapeake Inn Restaurant & Marina offers an outdoor tiki bar and deck. The Tap Room, on Bohemia Avenue, specializes in Maryland seafood, while on the North Side, Schaefer’s Canal House is well-known for its seafood.

Oakland

Oakland is the main commercial and cultural hub for Garrett County, the western part of the state. The downtown area features well-preserved 19th-century architecture. Located in the downtown area, the B&O Railroad Museum is housed in the 1884 rail depot, built in the Queen Anne style of railroad architecture. The building is listed on the National Register of Historic Places and was restored in 1998. Outside the museum sits the B&O locomotive No. 476, a Consolidation-type steam engine built in 1920, plus a caboose, and a green boxcar that houses the museum bookstore. Other museums include the Garrett County Museum of Transportation and the Garrett County Historical Society Museum.

The downtown district is lined with antique shops, cafes, and restaurants, including 206 Alder Bistro & Bar, which focuses on local ingredients and locally sourced beer, and Pawn Run Bar + Kitchen, a highly rated bar. Outdoor activities include hiking through old-growth forests in Swallow Falls State Park, home to Maryland's highest free-falling waterfall, Muddy Creek Falls. Herrington Manor State Park is 365 acres of activities, with a 53-acre lake and historic log cabins available for rent.

Leonardtown

Leonardtown is located in southern Maryland and is deep in coastal maritime culture. With its waterfront pier, Leonardtown is perhaps best known for the annual oyster-shucking championship. Downtown Leonardtown sits on the waterfront and is the only designated Arts & Entertainment District in Southern Maryland. This walkable commercial hub features 18th-century architecture, with shopping, galleries, and restaurants. Nearby, Shepherd’s Old Field Market is an indoor marketplace with over 70 local vendors, and Brudergarten is a beer garden. For food, there’s The Front Porch for Southern meals, and Olde Town Pub, a popular spot featuring pub fare.

There are several annual events in the town, taking place at Leonardtown Wharf Park or Leonardtown Square. The Summer Music Festival runs throughout warmer months, while Beach Party on the Square features the town center filled with sand. For outdoor activities, Leonardtown Wharf Park is on Breton Bay, with canoe and kayak rentals, a boardwalk, a floating dock, luxury catered picnics, an ice cream shop, and seaplane rides. Newtowne Neck State Park is a quiet park for hiking and has some secluded beaches.

Thurmont

Thurmont is known as the Gateway to the Mountains with its access to Cunningham Falls State Park and Catoctin Mountain Park, the latter of which is home to Camp David, the U.S. Presidential retreat. Thurmont is located in the north-central part of the state, ten miles from the Pennsylvania border. Thurmont was designated a Maryland Main Street Community and a National Main Street under the National Trust for Historic Preservation. To explore, the Thurmont Trolley Trail is a walking trail that starts in downtown Thurmont and connects to the Thurmont Regional Library. Murals on Main is a public art display of local history throughout the downtown, and The Vault 1891 is a renovated event space in a historic bank building on Main St.

Local dining options include Thurmont Kountry Kitchen, a highly rated old-school American eatery serving country fare, and Pupuseria Diana Marixa, a family-run Salvadoran restaurant. The town is a designated wine grape region, with several wineries, including Springfield Manor Winery, Distillery & Brewery, a 130-acre winery estate on the grounds of a 1774 manor. A key annual event in Thurmont is the Catoctin Colorfest, held at Community Park, featuring over 200 vendors, craftpeople, and food. This is one of the largest outdoor arts and crafts festivals on the East Coast, held annually in October and attended by over 100,000.

Take A Trip To The Small Towns Of Maryland

If you are looking for a small town that has a deep history, local color, and is friendly and welcoming, Maryland’s small towns are a perfect way to spend a weekend or longer. Whether you want to take a scenic drive through a few of these towns or stay put to get a deeper sense of the place, these small towns exemplify Maryland and America, from coastal charm to small-town friendliness.