6 Scenic Drives in Maryland You Won’t Want to Miss 

Despite its relatively small size, Maryland is a state that doesn’t disappoint when it comes to historical landmarks, picture-perfect landscapes, and relaxing country roads that wind for miles through forests, mountains, rivers, and farmlands.  

There’s nothing better than taking an afternoon or weekend to explore somewhere new, and Maryland is full of hidden gems just waiting to be discovered, all easy day trips from Washington DC.

Add these six scenic drives in Maryland to your calendar and embark on your next family adventure.  

6 Scenic Drives in Maryland 

1. Scenic Drives in Maryland:  Mountain Maryland Byway – Keysers Ridge to Cumberland  

  • Distance: 193 miles 
  • Time needed: 5-7 hours/2-3 days 

Experience the sweeping beauty of Maryland’s Western Mountains as you travel along the Mountain Maryland Byway. You can add this to your Maryland road trip itinerary, carve out an afternoon, or even take a day to explore miles of natural beauty.  

Begin your drive at Keysers Ridge, one of Maryland’s most scenic mountain peaks. From there, you can access a vast area of state parks and state forest land near Grantsville or take a winery tour in Friendsville. White-water rafting enthusiasts will also love the opportunities along the Youghiogheny River.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Youghiogheny River, Western Maryland

The Wisp Resort in McHenry is an adventure lover’s paradise. The resort offers a wide range of winter activities, such as snowboarding, skiing, and snow tubing. In the summer, fly through the air on a tree-top zipline tour, or hit a few rounds of golf. There are also multiple state parks along the route, such as Deep Creek Lake State Park and Swallow Falls State Park.  

There is something for everyone along this, making it one of the best Maryland scenic routes to visit year-round.

Pro Tip: Are you a serious hiker? If so, try hiking to the top of Backbone Mountain, Maryland’s highest point!  

When to go: Mountain Maryland Byway has something to offer visitors during every season, depending on your interests.  

2. Scenic Drives in Maryland: Chesapeake and Ohio Canal  – Hancock to Cumberland (MD 144 & MD 51) 

  • Distance: 57 miles 
  • Time needed: 2 hours/1 day 

This section of the Chesapeake and Ohio Canal Scenic Byway is the perfect way to spend a long afternoon, or you can easily spend the day exploring all that Hancock and Cumberland offer. There are plenty of sightseeing and outdoor activities to enjoy, making it an ideal route for families and individuals alike.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Paw Paw Tunnel, Maryland

The Paw Paw Tunnel is one of the highlights of your route. This historic tunnel is an engineering marvel, cutting through over 3,000 feet of rock. If you enjoy biking, be sure to visit the nearby Green Ridge State Forest. It has miles of off-road biking opportunities and is also renowned for its wildlife.  

End your drive in Cumberland, where endless culinary options await you. The 1812 Brewery and Queen City Creamery & Deli are just a few delicious options. After enjoying your meal, make time to visit the C&O Canal National Historical Park and Canal Place Heritage Area. You can take a boat tour, go shopping, or walk the Great Allegheny Passage Trail.  

When to go: We recommend taking this Maryland scenic drive in late spring, summer, or early fall. 

3. Scenic Drives in Maryland: Historic National Road  – Baltimore, MD to Keysers Ridge, MD 

  • Distance: 170 miles 
  • Time needed: 4-6 hours/2-3 days 

Famously known as “The Road That Built the Nation,” this portion of the Historic National Road stretches from the busy city streets of Baltimore to Pennsylvania’s state line.  There is much to see and do along the route, and you can easily spend a long weekend exploring the sights.  

If you’re beginning your drive in Baltimore, you’ll start along Lombard Street, the original start of the National Road. Boston’s Inner Harbor holds the perfect mix of shopping and dining spots. Visit historic sites like the Baltimore and Ohio Railroad Museum before traveling west to charming towns like Catonsville and Oella.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Cumberland Train Station, Maryland

Set aside a few hours to explore the iconic town of Frederick, where you can wander down Main Street, admire the century-old architecture, and take a tour of the National Museum of Civil War Medicine. If you wish, get some rest and relaxation at one of Frederick’s bed and breakfasts before moving on.  

Nature enthusiasts will love taking a detour to hike or bike through Fort Frederick State Park before reaching Cumberland, another town full of exciting things to see and do. You can ride a steam-powered train on the Western Maryland Scenic Railroad, visit the Toll Gate House in LaVale, and cross the Casselman River Bridge.  

When to go: You can travel the Historic National Road at any time of year.  

4. Scenic Drives in Maryland: Antietam Campaign  – White’s Ferry, MD to Sharpsburg, MD  

  • Distance: 126 miles 
  • Time needed: 3-4 hours/1-2 days 

Step back in time and journey over the historical land where the Battle of Antietam, a major Civil War conflict, was fought. You can easily make this drive in one day, and it’s the ideal way to spend a late summer or fall day walking in the footsteps of the thousands of both Union and Confederate soldiers.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Monocacy National Battlefield, Maryland

In September 1862, Confederate soldiers crossed into Maryland near White’s Ferry, where they fought against the Union in Poolesville. There, you can access several Civil War exhibits inside the John Poole House. As you travel north a few miles, you’ll reach the Monocacy National Battlefield, also known as the site of “The Battle That Saved Washington.”  

After driving through Frederick and beyond Braddock Heights, you’ll encounter South Mountain Battlefield Park, where intense battles were fought three days before the Battle of Antietam. This area is home to many historically significant buildings, and you can also take a tour of the Antietam National Battlefield.  

Pro Tip: December’s Antietam Memorial Illumination is a sight to behold, with 23,000 lights placed along a five-mile driving route.  

When to go: This Maryland scenic byway is enjoyable any time of year, and it’s worth checking out annual events happening in the area.  

5. Scenic Drives in Maryland: Old Main Streets  – Emmitsburg, MD to Mount Airy, MD (US 15, MD 77, MD 75 & MD 26) 

  • Distance: 85 miles 
  • Time needed: 2-3 hours/1-2 days 

If we could use one word to describe this Maryland scenic byway, it would be “local.” Winding country roads connect Emmitsburg, Westminster, and Mount Airy, where you’re invited to savor the local fare, explore local shops, and visit several local vineyards. We suggest spending a day (at least) to experience all that Old Main Streets has on offer.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Cunningham Falls State Park, Maryland

If you enjoy learning about local history, add the National Shrine of St. Elizabeth Ann Seton in Emmitsburg to your must-see list. As you travel south along US 15, stop for a hike or a picnic at Catoctin Mountain National Park or Cunningham Falls State Park. You can also view several mid-19th-century bridges in the area.  

Wine enthusiasts will love touring the three vineyards in Mount Airy, and this storybook hamlet is the perfect romantic getaway for couples. Next, you’ll head north to New Windsor and Uniontown. Take walking tours of Civil War-era homes, admire Victorian architecture, and browse local antique shops.   

When to go: Although you can travel the Old Main Streets any time of year, it’s the most fun to browse local shops and vineyards in summer and fall, when you can enjoy the Maryland scenery at its best. 

6. Scenic Drives in Maryland: Mason and Dixon Scenic Byway – Westminster, MD to Appleton, MD (US 15, MD 97, MD 25, MD 136, US 1 & MD 273)  

  • Distance: 143 miles 
  • Time needed: 3-5 hours/1-2 days 

You might have heard of the Mason-Dixon Line, but this rural Maryland scenic byway brings the story to life. This winding drive south of the Pennsylvania border is full of pastoral farmlands and historical sites that capture the purpose and spirit of 19th-century Americans.  

You’ll begin your journey in Westminster, where early farmers got their start and Civil War soldiers stopped on their march to the Battle of Gettysburg. As you travel on, make sure to stop in Manchester, where you can sip the fruit of the vine at a family-owned vineyard.  

USA 6 Scenic Drives in Maryland You Won’t Want to Miss - Conowingo Hydroelectric Plant, Maryland

The Torrey C. Brown Rail Trail is another interesting stop. This 20-mile stone-dust path was once a railroad bed that ran from Hunt Valley to the Mason-Dixon Line. Pro Tip: Rent bikes from a local vendor to bike the length of the trail. After that, move on to the Conowingo Hydroelectric Plant, one of the nation’s biggest hydroelectric generating stations. It spans the Lower Susquehanna River, where you can also fish for small-mouth bass and watch for local wildlife.  

From there, you’ll move on to the rural area between Harkins and Appleton. These towns are well-known for their farm stands, hayrides, and corn mazes in the fall. If you’re traveling with kids, make sure to visit Rising Sun. They can see the many species of animals at Plumpton Park Zoo and even feed the giraffes!  

When to go: We recommend exploring this Maryland scenic byway in the summer and early fall, as the fall foliage is splendid to view!  

Explore More of the East Coast

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