8 Cute Small Town Drives In Maryland

The cutest small town drives in Maryland are as much about the history along the backroads as the towns at either end. In Chestertown, roadside markers and Washington College hint at George Washington's many connections to the town. Chaptico has an even older story, having grown as a shipping and trade port before the Wicomico River silted up. And in Bellevue, the Oxford-Bellevue Ferry still crosses the Tred Avon River, continuing a route that dates back to 1683. These eight small town drives pair that history with farmland, woods, and waterfront views, so the time behind the wheel is as enjoyable as the stops along the way.

Berlin to Snow Hill

To see the quieter side of the Eastern Shore in Maryland, take a drive from Berlin to Snow Hill. It's a short drive at only 15 miles, but there's a lot to see along the way. After leaving the historic streets of Berlin, the road makes way for farmland, woods, and open countryside. The landscape becomes even more wooded as Snow Hill gets closer, and the Pocomoke River adds water to the view. This area is part of Maryland's Cape to Cape Scenic Byway, which passes through Berlin and Snow Hill before continuing to Stockton and the coast. Stockton also makes a simple, small-town detour, with all three towns connected by rural roads through some of Worcester County's most open landscapes. The short drive leaves enough time to stop off in town, explore a side road, or practice those photography skills, which suits a slow afternoon.

St. Michaels to Oxford

There's a little bit of everything on the drive from St. Michaels to Oxford, including farmland, small towns, views of the water, and even a ferry ride. From St. Michaels, the route heads through Royal Oak to Bellevue, with views changing from waterfront homes and boats to wide open fields and tree-lined roads. In Bellevue, take the Oxford-Bellevue Ferry across the Tred Avon River to Oxford. The crossing is the highlight of the trip, with sunlight on the water and boats of all kinds out on the river. Taking the ferry keeps the drive to about 9 miles and around 45 minutes, while skipping it means looping through Easton, which stretches the route to about 20 miles.

Chestertown to Rock Hall

With just 13 miles between Chestertown and Rock Hall, the drive is short, but it still makes for a relaxing trip into the Eastern Shore countryside. Instead of spending all day on a major highway, explore quiet Kent County on a 20-minute drive. The road out of Chestertown passes farm fields, old houses, woods, and occasional glimpses of water, and it starts to feel more coastal as the drive nears Rock Hall and the Chesapeake Bay becomes a bigger part of the landscape.

Chestertown gives this drive a historic starting point, known for its annual Chestertown Tea Party Festival and for Washington College, where George Washington served on the original Board of Visitors and Governors. To stretch the trip, add a side trip to Galena, a town where Washington stopped on his way to and from the First Continental Congress. From Rock Hall, smaller roads lead toward the waterfront and surrounding countryside, but you may want to spend more time in friendly Rock Hall, where it's customary to wave or nod at everyone you pass on Main Street.

Sykesville to Mount Airy

To get away from Maryland's flatter Eastern Shore, take the 25-minute drive from Sykesville to Mount Airy. This roughly 14-mile route winds through the countryside of central Maryland, where the extra hills, curves, and tree-lined roads set the scenery apart from the Eastern Shore. Taking the drive in the fall adds even more color for photos. The wooded hills and Patapsco River frame Sykesville at the start. As the road heads west, stretches of woods break up the views of farms and open fields before the route reaches Mount Airy, an old railroad town that got its start as a settlement in the 1830s. New Windsor, known for its preserved 19th-century architecture, is another worthwhile small-town stop, and Maryland's Old Main Streets Scenic Byway connects it with Mount Airy. Be sure to check out some of the rural roads instead of following the fastest route through.

Port Deposit to Perryville

With just six miles between them (12 minutes), the drive from Port Deposit to Perryville is one of the shortest routes on this list, but the scenery makes up for it. Port Deposit sits along the Susquehanna River, with wooded hills rising behind the town, and river views stay a big part of the scenery as the road heads toward Perryville. In Perryville, stop by the historic Rodgers Tavern Museum, which offers free admission. The tavern was once a resting place for Revolutionary War figures, including George Washington and the French generals Lafayette and Rochambeau. To make the drive a bit longer, continue toward Havre de Grace, which is packed with history. The town is said to have missed out on becoming the US capital by a single vote, and it served as a crucial crossing point over the Susquehanna River for freedom seekers escaping slavery on the eastern route.

Leonardtown to La Plata

Driving from Leonardtown to La Plata is a good way to get to know Southern Maryland. It's a longer drive at about 45 minutes, but it covers 30 miles of farmland, woods, old homes, and small communities. Downtown Leonardtown is the only designated Arts & Entertainment District in Southern Maryland, so be sure to explore the art galleries before heading out.

Along the way is the small town of Chaptico, which was established as a port of entry in 1683 and served as a shipping hub until the Wicomico River filled with mud, making boat travel impossible. Fill up on scratch-made comfort food at Chaptico Market & Deli before getting back on the road, where the route curves through wooded areas and climbs hills before opening onto fields. With the Religious Freedom Scenic Byway running through Leonardtown and other Southern Maryland communities, it's easy to extend the drive and explore more.

Mount Airy to New Market

The drive from Mount Airy to New Market is another short one. The two towns are only 8 miles apart, making the trip about 13 minutes, but stops in New Windsor or Uniontown can stretch it to fill a weekend morning or afternoon. Because Mount Airy is surrounded by farmland in central Maryland, the roads leaving it quickly turn rural. Almost the entire village of Uniontown makes up the Uniontown Historic District, which was added to the National Register of Historic Places in 1986. Its mostly 19th-century houses and buildings still read as a rural village from that era. Continuing on to New Market, the curvy road passes old farmhouses through a mix of open and wooded areas. New Market makes a fitting endpoint for those interested in a little antique shopping, as it is known as the "Antiques Capital of Maryland."

Snow Hill to Pocomoke City

The 17-minute drive from Snow Hill to Pocomoke City makes for a pleasant outing in either direction. Both towns are near the Pocomoke River, but most of the route between them runs through rural Worcester County, where, like other drives on this list, the road winds through fields and wooded areas. With a detour south to Stockton, stop for lunch at the Timeless Tavern for classic American food, and for those wanting a drink, they offer "the coldest beer on the Shore." Many Stockton residents now work nearby at NASA's Wallops Flight Facility. It may be small with fewer than 100 residents, but there are still things to see, including a few historical cemeteries and the 1850 Holy Cross Episcopal Church, considered "Stockton's Historical Jewel." Side roads lead to other sweet spots, such as the pier at Public Landing or George Island Landing, also known as the "Oyster Capital of the World."

Take the Scenic Route

History comes alive on these cute small-town drives. Ride a ferry route that dates to 1683, follow the road George Washington took to the First Continental Congress, or browse antiques in the town known as Maryland's antiques capital, and the miles between stops start to feel like part of the story. With eight intriguing routes to choose from, you may just end up doing them all. So pick a route, leave extra time for exploring, and see where the drive takes you.