Coast to Countryside: Road Trip Across Maryland

To kick off your trip, fly into Baltimore-Washington International Airport (BWI), rent a car and take the quick drive to one of the many hotels near scenic Baltimore Harbor. Hop on a Baltimore Water Taxi for an hour-long cruise to get a quick overview of the area before diving into its many wonderful neighborhoods. Visit lively Federal Hill to check out the American Visionary Arts Museum, a one-of-a-kind display of outsider art on the south shore of the Inner Harbor. The museum features paintings and sculptures created by self-taught and intuitive artists outside the typical realm of the art world. Ready for a drink and a snack? Head to Union Collective, a group of independently owned, Baltimore-based businesses housed under one roof. Sip some local beers at Union Craft Brewing and sample some locally made ice creams at The Charmery, known for inventive flavors like Fresh Mint & Figgy Lime and Purple Rain (cabernet-caramel ice cream with dark chocolate Stracciatella). It’s the perfect way to end your time in Baltimore on a sweet note before heading to your next destination.

It’s less than an hour’s drive from Baltimore to Annapolis, a quick trip south on Interstate 97 to the Chesapeake Bay. Take a tranquil pause in Maryland’s waterfront capital city, starting with a peaceful stroll at Historic London Town & Gardens. Designated a Site of Memory by the UNESCO Slave Route Project, the 9-hectare site on the South River recreates a 1683 colonial town surrounded by woodland and ornamental gardens. Drive across the Severn River for lunch at the iconic Cantler’s Riverside Inn, known for serving Maryland blue crabs and other fresh-from-the-bay seafood. Walk off your meal with a tour of the U.S. Naval Academy, home of the 4,400-strong Brigade of Midshipmen and the official training ground for future officers in the U.S. Navy and Marine Corps. Spend the rest of the afternoon browsing the brick-lined streets of Annapolis’ Historic District, a "museum without walls" showcasing four centuries of architecture. In the evening, board the Schooner Woodwind to compete in the Wednesday Night Sailing Races or catch the boating action from City Dock. More than 100 crews depart the Annapolis Yacht Club each week in a tradition that spans more than 60 years. As you watch the colorful spinnakers fill the twilight sky, you’ll understand why Annapolis is often called "America’s Sailing Capital."

After spending the night in Annapolis, take the short drive to Howard County in central Maryland. The area is a pleasing mix of urban, historic and rural experiences. Along the way, stop in Laurel to walk over the Little Patuxent River across the Bollman Truss Railroad Bridge, an engineering feat and National Historic Landmark. Next up, browse another historic locale, Savage Mill, once a textile mill that’s now a mixed-use space complete with dining, shopping and art galleries. It’s the perfect rest spot for a little shopping, plus a sweet treat and a drink. Travel north through the rolling green hills to go back in time at Historic Ellicott City, a 250-year-old mill town. The area features the oldest train station in the USA and more than 70 shops, restaurants, galleries and museums. Finish your day in Howard County in Columbia in the bustling new Merriweather District, a mixed-use residential development that includes trendy shops and restaurants. Maybe you’ll even catch a live poetry reading at community-minded coffee shop Busboys and Poets.

After a restful night in Howard County, it’s a quick jaunt west to scenic Frederick. Stop just outside town at the Monocacy National Battlefield, the site of a significant 1864 American Civil War battle known as the “Battle that Saved Washington.” Hike the park’s six trails or opt to see the sights and learn about the battle by car. Later, drive to downtown Frederick to stroll the placid creekfront. Carroll Creek Park wends its way through the city’s center, offering its serene, waterfront views to shops, breweries and outdoor restaurants along its brick pedestrian path. The area also includes a 350-seat amphitheater and is known for its playful fountains, multiple walking bridges and picture-perfect lily pads. Wrap up the day (and your Maryland road trip) with dinner and cocktails on the patio at Up on Market, a prime spot to savor downtown Frederick as the sun sets. The bistro is housed in a restored 1770s building that also has a four-room inn called Inn on Market, in case you’re in search of a quaint place to stay the evening. In the morning, you’ll drive about an hour back east on Interstate 70 to the airport in Baltimore.