9 Great Road Trips to Take in Maryland

Driving through Maryland is a journey through the state's rich history and diverse landscapes. From the bustling harbor of Baltimore to the rugged peaks of the Appalachian Mountains, each road trip is a unique window into the Free State's natural beauty and cultural heritage. Whether you're seeking a scenic coastal escape, a mountain adventure, or an immersion in colonial-era sites, these carefully curated itineraries are an excellent starting point for planning your Maryland road trip.

Baltimore to Ocean City

The journey from Baltimore to Ocean City takes travelers across the Chesapeake Bay Bridge into Maryland's Eastern Shore. Begin in Baltimore's Inner Harbor before heading east on I-97 to US-50. Your first essential stop should be Kent Island, where Fisherman's Inn has classic Chesapeake Bay seafood with views of the bridge you just crossed. Continue east to Cambridge, where the Harriet Tubman Museum & Educational Center provides insights into the Underground Railroad and the region's role in civil rights history. Before reaching the coast, detour to Berlin. It is recognized as "America's Coolest Small Town," where 19th-century architecture houses local shops and eateries. Finally, reach the Ocean City Boardwalk, where Thrasher's French Fries and Trimper's Rides are the perfect beach town welcome.

Frederick to Deep Creek Lake

The westward journey from Frederick to Deep Creek Lake showcases Maryland's mountain landscape. Starting from historic downtown Frederick, take I-70 west to I-68, climbing through the Appalachian Mountains. South Mountain Battlefield is the first stop, with trails through Civil War history. In Cumberland, The Western Maryland Railway Station operates as a museum dedicated to the region's railroad heritage and has historical context for the area's development. Before reaching the lake, New Germany State Park offers forest trails for stretching road-weary legs. The destination, Deep Creek Lake State Park, rewards travelers with Maryland's largest freshwater lake, complete with boat rentals and swimming areas.

Baltimore to St. Michaels

The route to St. Michaels begins in Baltimore's harbor and crosses the Bay Bridge into the Eastern Shore's peninsula. Kent Narrows serves as the first stop, where Harris Crab House has front-row seats to working waterfront views and fresh seafood. Proceed to Easton, where the Academy Art Museum hosts both regional and national artists in a historic setting. Tilghman Island, a working watermen's village, has views of the bay and insight into the region's maritime culture. End at the St. Michaels Maritime Museum, where visitors learn about Chesapeake Bay's boatbuilding heritage and maritime history through interactive exhibits and restored vessels.

Annapolis to Solomon's Island

From Maryland's capital, Annapolis, follow MD-2 south through Calvert County toward Solomon's Island, a route that winds through tobacco fields and past rivers feeding into the Chesapeake Bay. Begin the journey with a stop at Greenstreet Gardens in Lothian, which has plants and produce specific to the region, plus seasonal activities like pumpkin patches in fall and Christmas trees in winter. Calvert Cliffs State Park is great for fossil hunting along the shoreline. Calvert Cliffs State Park presents your next stop, with beaches known for Miocene-era fossil discoveries like shark teeth, and hiking trails that wind through wooded cliffs. For a final pitstop, check out the Calvert Marine Museum, home to the Drum Point Lighthouse and exhibits detailing the region's maritime heritage and prehistoric past.

Frederick to Harper's Ferry

This route follows US-340 from Frederick through the Catoctin Mountains into West Virginia, passing through landscapes that witnessed key moments in Civil War history. Begin at the Catoctin Wildlife Preserve, where native species show the region's biodiversity and guided tours reveal local wildlife conservation efforts. Brunswick is the second stop, with its Railroad Museum documenting the town's significance in the B&O Railroad's history through restored rail cars and interactive exhibits. The C&O Canal is an excellent third stop, with walking and biking opportunities along the historic towpath where mules once pulled canal boats laden with cargo. Local outfitters rent bikes and kayaks to explore the canal and Potomac River. Then, end in the town Harper's Ferry.

Baltimore to Assateague Island

The trek to Assateague begins in Baltimore, following I-97 to US-50 before turning south on MD-611. Stop first in Salisbury at the Ward Museum of Wildfowl Art to discover the Eastern Shore's waterfowl heritage. Public Landing is a good choice for the next stop, with views of traditional waterfront life. Be sure to also drop by the NASA Wallops Flight Facility Visitor Center, which presents space research initiatives on the coast. Assateague State Park is the grand finale of the road trip, where wild horses roam the beaches and dunes. It is a unique contrast to the journey's starting point in Baltimore.

Cumberland to Rocky Gap State Park Loop

This mountain circuit begins and ends in Cumberland, following I-68 and MD-144 through the Allegheny Mountains. It runs through some of Maryland's most dramatic mountain scenery. The Cumberland Narrows is the first stop, overlooking the historic mountain gap that served as a crucial transportation route for early settlers and the railroad industry. Rocky Gap Casino has gaming and dining options along the route, plus a golf course. Lake Habeeb has opportunities for fishing and kayaking in mountain surroundings, with rentals available seasonally and beaches for swimming. The Mountain Maryland Trail system is the final stop, with hiking options through mountain terrain and forest landscapes, connecting historic mining towns.

Hagerstown to Catoctin Mountain Park

The drive east from Hagerstown on US-40 traverses the Cumberland Valley into the Catoctin Mountains, following routes used by settlers and traders since colonial times. Begin at South Mountain Recreation Area, accessing portions of the Appalachian Trail and Civil War battle sites that played roles in the Maryland Campaign. Cunningham Falls is Maryland's highest waterfall as the second stop, with multiple hiking trails leading to views of the water and surrounding forest. The Catoctin Wildlife Preserve has additional trails through mountain habitats and hosts educational programs about local ecology. Finally, make it to Mount Aetna, where overlooks provide panoramic views of the valley below, and interpretive signs explain the geological forces that created these ancient mountains.

Baltimore to St. Mary's City

This journey through southern Maryland follows MD-2 south to MD-235, passing through historic tobacco country. Battle Creek Cypress Swamp is recommended as your first stop, with boardwalks through wetland ecosystems. Continue driving until you reach the Sotterley Plantation, offering tours of an early 18th-century mansion. Third, Point Lookout State Park, the site of a Civil War prison camp, provides historical context and bay views. The journey ends at St. Mary's City, where a living history museum recreates Maryland's first colonial capital through archaeological sites and ship replicas. Costumed interpreters demonstrate colonial crafts while archaeologists continue to uncover artifacts from Maryland's earliest European settlement.

Start Your Maryland Road Trip Adventure

Whether you're a lifelong resident or a first-time visitor, these road trips provide an opportunity to explore Maryland's remarkable regional diversity—from the Chesapeake Bay's shores to the rolling hills of tobacco country and the ancient Appalachian peaks that tower above it all. No matter which route you choose, one thing is certain: a Maryland road trip will leave you with lasting memories and a deeper appreciation for the state's natural wonders, historic sites, and charming small towns. So pack your bags, fire up the car, and get ready to experience the many delights that await you on the roads of the Free State.