9 Most Scenic Drives in Maryland

Some roads are built for getting somewhere fast. Others are meant to be savored. The most scenic drives in Maryland fall firmly into the second category.

These routes wind past mountain overlooks, trace the edges of the Chesapeake Bay, cut through farmland, and roll into small waterfront towns where it’s worth pulling over. You’ll pass historic main streets, quiet forests, open water views, and stretches of shoreline that feel far removed from busy highways.

If you’re looking for a drive with great views and plenty of reasons to slow down, these nine scenic routes deliver exactly that.

Mountain Maryland Byway

• Approximately 4 to 6 hours
• 193 miles

The Mountain Maryland Byway is a perfect excuse to trade sandy shores for mountain air and wide-open views. This 193-mile drive winds through the foothills of the Appalachian Mountains, starting high up on Keyser Ridge. It is one of Maryland’s highest points, where you can look out over thick forests and rolling hills. From there, the road heads west with glimpses of the Youghiogheny River along the way, then dips south toward Deep Creek Lake. This spring-fed lake stretches for 13 miles, with 65 miles of shoreline. It has something in every season, from boating and hiking to winter fun at nearby Wisp Resort, where snowboarding and skiing keep things lively when the temperatures drop.

As the drive continues, Oakland makes a great place to slow down. Grab lunch, browse a few local shops, or plan to attend the colorful Autumn Glory Festival. The town’s historic train depot and small-town charm make it an easy spot to spend the night if extending the byway into a two-day adventure is the plan. From Oakland, there are two options: MD 495 leads you past places like the Spruce Forest Artisan Village, while MD 135 delivers jaw-dropping scenery as it cuts through Savage River State Forest. Either way, the drive will pass through historic mountain towns like Grantsville and Frostburg before rolling into Cumberland, where museums, galleries, and sweeping mountain views wrap up the journey.

Historic National Road

• Approximately 4 to 6 hours
• 173 miles

For drivers starting in Baltimore and itching for a road trip with a good story behind it, the Historic National Road is a great pick. This 173-mile drive can be done in about 4 to 6 hours. However, it’s much more fun if you take your time and turn it into a multi-day adventure. It was originally traveled by covered wagons and pioneers headed west in search of new opportunities. This road once connected Maryland with the then-distant Illinois. Begin at Baltimore’s Inner Harbor and follow Lombard Street through historic neighborhoods like Union Square before easing out of the city and into Catonsville and Oella, both charming towns with roots going back to the 1800s.

One of the first must-stop moments comes after crossing the Patapsco River. It's here that the train bridge for Old Ellicott City advertises itself like a proper welcome sign. This is a perfect place to stretch your legs, browse Main Street shops, grab a meal, or dive into local history at the B&O Railroad Station Museum. For history buffs, be sure to check out Thomas Isaac’s Log Cabin, which once served as a way station for travelers on the National Road. Heading west, the drive strings together classic Maryland towns like Mount Airy, Frederick, Braddock Heights, and Boonsboro. Along the way there are plenty of museums, scenic views, and overnight options to choose from.

The Maryland portion of the route wraps up near the Pennsylvania line. In LaVale, keep an eye out for the state’s last remaining toll gate house. It's complete with a plaque listing historic toll prices for wagons, animals, and pedestrians. From there, Route 40 carries you through the peaceful Savage River State Forest. This journey ends at the Mason-Dixon Line, a quiet end to a history-filled drive on a road that helped shape the nation.

Historic Charles Street

• Approximately 1 to 2 hours
• 12 miles

Historic Charles Street cuts right through the heart of Baltimore. This 12-mile route starts at the Inner Harbor and ends in nearby Lutherville. Kick things off downtown then head toward Fells Point or swing by Cross Street Market if hunger strikes early. Heading north, Charles Street shows off some of the city’s greatest sights, from the former B&O Railroad headquarters to the grand Hippodrome Theatre. All around you are layers of Baltimore history, colorful murals, and architecture that tells stories from different eras.

Continuing north, roll into Mount Vernon, one of the city’s most striking neighborhoods. Visit the Basilica of the National Shrine of the Assumption of the Blessed Virgin Mary, America’s first cathedral. You'll also see one of Maryland’s earliest independent churches. The towering Washington Monument is a pillar in the neighborhood, surrounded by leafy streets and elegant buildings. That calm, historic vibe slowly gives way to the creative energy of the Station North Arts District. Here, you’ll pass the Charles Theatre, once a streetcar barn and dance hall.

Next comes Charles Village, one of Baltimore’s earliest suburban neighborhoods. It blends seamlessly into the campus of Johns Hopkins University and the stately columns of the Baltimore Museum of Art. The drive then becomes quieter and greener as you cruise through Roland Park, with its tree-lined streets and beautiful homes. In just a few minutes, you’ve left the city behind and arrived in Lutherville, a charming Victorian neighborhood that makes a fitting, peaceful end to this classic Baltimore drive.

Cape to Cape Scenic Byway

• Approximately 2.5 to 3.5 hours
• 79 miles

Maryland’s Eastern Shore feels like a world apart, and the Ocean City to Stockton Byway is a great way to experience both its coastal energy and quiet countryside. This 79-mile stretch is part of the larger Cape to Cape Scenic Byway, but Maryland’s portion keeps things easy and scenic. The drive begins in lively Ocean City, where a 10-mile beach, classic boardwalk, and family-friendly attractions set the tone. Head south on Route 611, where the pace quickly slows. You’ll pass Assateague Island and settle into wide-open views with flat farmland, weathered homes, and occasional flashes of the Atlantic that remind you just how close the water always is out here.

From here, take 376 west, and enter Berlin. This postcard-worthy town is known for its historic brick buildings and quirky shops. Cross onto Route 113 to explore Snow Hill, a small town with a big sense of history and culture. The Julia A. Purnell Museum offers a thoughtful look at centuries of Native American life on the Eastern Shore, making it a worthwhile stop before the final stretch. Next, follow MD 12 into Stockton, a quiet bayside town dotted with antique homes and classic Eastern Shore charm. This is where the Maryland portion of the byway wraps up although if you’re feeling adventurous, the road continues into Virginia with even more to explore just beyond the state line.

Roots and Tides Scenic Byway

• Approximately 1.5 to 2.5 hours
• 47 miles

The Chesapeake Bay is at the heart of Maryland life, and the 47-mile Roots and Tides Scenic Byway puts it front and center. The drive begins in Annapolis, the state capital. Here cobblestone streets and beautiful 18th-century buildings make it worth lingering a bit before hitting the road. Head south, and pass places like Historic London Town and Gardens and the Smithsonian Environmental Research Center. This route sticks close to the water, but don’t expect that strong ocean smell. The Chesapeake Bay is brackish, so it feels coastal without the salty bite.

While the views from the car are lovely, this byway really shines when you step off the road and onto the water. In Edgewater, you can charter a boat and explore the Bay’s creeks and coves up close. Alternatively, head to the historic village of Galesville to sail on a traditional ketch that’s been part of the community for generations. As you continue down MD 423 toward Prince Frederick, the pace stays relaxed. This is a great spot to stop at Running Hare Vineyard for a glass of wine. The Battle Creek Cypress Swamp Sanctuary also delivers the perfect place for a peaceful walk, with towering trees and boardwalks.

Chesapeake Country Scenic Byway

• Approximately 12 to 17 hours
• 419 miles

The Chesapeake Country Byway is a 419-mile tour best stretched out over several days since it can easily take more than 16 hours to drive through everything. Begin in Chesapeake City looking over the Chesapeake and Delaware canal. Take MD 213 south through the twisting roads filled with the natural beauty of the region before getting a peek at historic Georgetown. Continuing into the town of Betterton you can spot Victorian era architecture on your drive, and then get a look at the colonial port town of Chestertown.

Hop over to MD 50 and pass through the wide swathes of farmland and flat expanses that make up this part of the state, before passing through Denton and Easton. Driving through these small towns you’ll notice plenty of older buildings, because this rural area has a history that goes back more than 300 years. In Talbot County, it’s worth taking a quick break to check out Frederick Douglass Statue at the courthouse, and tour the Mitchell House where his sister lived.

For the last leg of this trip you can travel north to Federalsburg for a more idyllic drive, where you can enjoy the creek from the Idylwild Wildlife Management Area, or head east towards the bustling city of Salisbury. From there head to the southernmost point of Maryland in Crisfield for local seafood. This is where the drive ends, although it is worth hopping a ferry over to Smith Island, Maryland’s only inhabited island accessible by boat.

Journey Through Hallowed Ground National Scenic Byway

• Approximately 2 to 4 hours
• 57 miles

Maryland packs a lot into a small space, and the Hallowed Ground Byway is a great way to see that up close. This 57-mile drive runs south to north from the Maryland-Virginia line to the Maryland-Pennsylvania line. It’s the kind of route that mixes natural beauty with layers of history without ever feeling rushed. This drive starts in Point of Rocks where charming views kick things off. In the autumn the leaves take center stage, while spring delivers blooming color from the flowers. From there, follow US 15 north along the Catoctin Mountain Highway, where the scenery alone is enough to make you glad you took the drive.

Before you get too far, you’ll hit Frederick, one of those towns that deserves a pause. Wander around on a guided walking tour, and admire the well-preserved 18th- and 19th-century architecture. The National Museum of Civil War Medicine is also well worth a visit. Nearby, Catoctin Furnace offers a deeper dive into the past. From the restored Forgeman’s House to lively events like the Maryland Lavender Festival and the Maryland Iron Festival. As you continue toward Thurmont, you’ll pass the peaceful National Shrine Grotto of Lourdes. Then hop onto Route 77, to cross the Appalachian Trail. Then, the byway loops you back toward Frederick, carrying you under the Utica Covered Bridge.

Mason & Dixon Scenic Byway

• Approximately 1.5 to 2.5 hours
• 143 miles

This scenic byway just south of the Pennsylvania border is the kind of drive that invites you to roll down the windows. With 143 miles of history and countryside waiting for you to explore. The route follows part of the Mason-Dixon line with stories of early America, local history, and Maryland’s farm roots. Get started in Westminster where you can enjoy the Carroll County Farm Museum or catch a show at the Carroll Arts Center. Further north the Union Mills Homestead brings together history from both Union and Confederate soldiers during the Civil War. The road takes you through small towns and rolling farmland before opening up to outdoor gems.

Crossing the Susquehanna at Conowingo Dam delivers shop stopping views with bald eagles soaring overhead. Along the way, Rising Sun shows off with vineyards and drag racing. The nearby Fair Hill Natural Resources Management Center is another win for nature lovers with equestrian trails, trout fishing, and plenty of options for hiking. End the drive in Appleton.

Lower Susquehanna Scenic Byway

• Approximately 1 to 2 hours
• 33 miles

This 33-mile drive runs from Havre de Grace to Perryville; perfect for a single day but can easily be stretched into a weekend. The Susquehanna River delivers beautiful water views, amazing birding opportunities, and plenty of places to paddle or fish. Start in Havre de Grace, a quiet waterfront town bursting with antique shops, museums, and riverside dining. The Concord Point lighthouse and Duck Decoy Museum are worth checking out before hitting the road.

Moving upriver, the scenery moves from small towns to rugged nature with forests. See hidden historic sites in Susquehanna State Park. A detour to Conowingo Dam will let you spot bald eagles, herons, and hawks before you proceed into Port Deposit. This town is a great place to stop and stretch your legs with 1800s homes, and a riverwalk where you can enjoy the Susquehanna without needing to keep your eyes on the road. Perryville is the end of the road, but it has plenty to explore.

The Scenic Byways are Waiting for You

Maryland’s back roads are full of surprises. Quiet waterways along the Eastern Shore contrast with rolling farmland and Appalachian foothills in the west, each scenic drive highlighting a unique side of the state. History buffs will find plenty to explore and nature lovers can enjoy scenic vistas, hiking trails, and forests rich with wildlife. Family-friendly stops and overnight lodging let travelers adjust plans as they go. With historic markers and open roads, these routes invite a slower pace to truly experience Maryland.