Road TripsTravelers

Top Maryland Road Trip Destinations – Take A Memorable Tour

Mountaian Maryland Byway - Top road trip destinations

If you’ve been planning for a one of a kind road trip escapade for long, you might want to consider cruising the state of Maryland. It’s a unique getaway destination featuring beautiful Mid-Atlantic coastline and scenic mountains that reveal the colorful character of the state. So explore our sampling of top Maryland road trip destinations.

Bearing in mind that the US’s national anthem came from Maryland, the state is among the top in terms of rich history about the country, dating back to the pre-colonial era. You can never run out of fun activities to indulge in, and the presence of Washington County Museum of Fine Arts, Swallows Falls State Park, House of Yoda plus many more will attest to that. 

We’ve done the legwork of sampling top destinations in Maryland and came with this list. Check out some of the destinations we think will impact memories of a lifetime! If you are thinking about the budget, have a look at some cheap things to do in Maryland also.

Below slides give you a speedy account of why Maryland can be a merry land for road trippers:

Annapolis, Maryland’s Capital – The Naval Connection

Top Maryland Road Trip Spots- Annapolis, The Capital City

Annapolis is one of the topmost Maryland road trip destinations. If you haven’t been to Annapolis before, you might want to make use of this opportunity to explore some of the finest attractions in the city. If you visit downtown, you’ll experience a historic splendor from the city’s architecture, with a greater portion of it dating back to the 17th century. There are also architectural structures dating back to the 18th and 19th centuries that will make this visit worthwhile. 

Head down to Annapolis City Dock and spend some quality time as you view the beauty it presents. Apart from viewing the midshipmen of the Naval Academy carrying out exercises in their uniform, there’s plenty of activities at the dock also, such as live music bands and huge ships entering and exiting on a daily basis. 

You can also go on a guided tour at the United States Naval Academy, which can be organized by visiting Armel-Leftwich Visitor Center. 

The Historic Town of Frederick – Antiques, Art & More!

Antique lovers, pack up your car and get ready to explore amazing antiques that this small town has to offer. Tracing its origin back to the mid-18th century, the small town of Frederick has managed to maintain its historic atmosphere making it among the top favorites for visitors to Maryland. 

It houses several amazing antique local dealers, artists, and malls with great displays to catch anyone’s fascination. The town also has quite many historic homes, like Barbara Fritchie’s House among others which can be explored during this trip. Barbara Fritchie’s House is among the most attractive historic homes here; its period décor furnished and contains classic furniture from the colonial era. 

This is one of the unique Maryland road trip destinations. If coming here purposely for antique souvenir shopping, then you need to start with Market Street. Another larger alternative you might want to visit also is the Francis Scott Key Mall. 

Antietam National Battlefield – American Pride & Civil War History

Top Maryland road trip spots- Civil War History & Museum

If you’d love to share in the American pride by learning about the country’s military history, you should visit the Antietam National Battlefield. The Battle of Antietam is recognized as America’s bloodiest day in the history of the military. 

You can make your visit here worthwhile by starting at the Visitor Center. There’s an almost 9-mile route tour complete with audio, just perfect for Civil War history devotees. Next, visit Pry House Field Hospital Museum where you’ll get to see amazing exhibits showcasing various things that nurses and doctors had to deal with in the course of the war. 

Last but not least, you can enjoy the scenic views of the beautiful landscape as well as participate in fun-filled adventure activities such as hiking along Union Advance Trails or the Antietam Remembered Trails. When planning a trip to the state, it is one of the top Maryland road trip destinations.

Muffler Men at Berlin and Ocean City  – Unique Maryland Attraction

If you’re a travel enthusiast and have visited virtually every corner of the country, you probably have come across the quiet fiberglass sentinels along highways of the US. Most of these huge “muffler men” came to be called so as initially they used to auto repair shop adverts, but now have a new purpose. 

There’s a Muffler Man standing as a cowboy with an ice cream cone in his hands, watching over a western-themed water park, the Frontier Town. Yet another one has found new duties as a pirate, standing with a cutlass and an eye-patch at the gates of Jolly Roger Amusement Park in Ocean City. 

Bollman Truss Bridge – Only Remaining Example

Bollman Truss Bridge - Railroad history of Maryland

Everyone loves old structures not only for the beauty they portray but also the magnificent strength and durability they showcase. And you’re definitely going to love this historic bridge. Bollman Truss Bridge found in Savage, is the only remaining example of a bridge portraying the revolutionized railroad bridge style of the 19th century. 

Constructed in 1869, this all-iron structure mainly served the Baltimore and Ohio mainline but was later abandoned due to old age and the too much weight of the trains. Today, it is designated for light usage such as carrying pedestrians across Little Patuxent River. 

In 1966, Bollman Truss Bridge was designated as the first US’s National Historic Civil Engineering Landmark to be recognized by the American Society of Civil Engineers. In 2000, the bridge was named as a National Historic Landmark by the National Park Service. It’s a great destination to visit and learn a lot about the expertise in early engineering. 

Mountain Maryland Byway – 193 Miles of Road Trip

This byway stretches about 193 miles starting from Keyser’s Ridge heights to the historic Cumberland. Mountain Maryland Byway is a great road trip choice that will let you tour the great and glorious Western Maryland geography. 

This road trip is offering a transcendental experience especially if traveling during fall when the vegetation turns color. It cruises through the Youghiogheny River then plunges into the Alleghenys, giving you a fulfilling satisfaction for a road trip crave. The scenery along this route is magnificent so you might want to make stops and view the beauty and perhaps capture some photos for long-lasting memories of this trip. 

Dr. Samuel A. Mudd House Museum  – Lincoln Heritage

Maryland's Lincoln History - Dr. Samuel A. Mudd House Museum

This museum has quite a bountiful story about the history of the assassination of Abraham Lincoln, one of the greatest presidents. Located new Waldorf, Dr. Samuel A. Mudd House, also called St. Catharine Museum is a historic house you need to visit to get a deeper insight into Lincoln’s assassination story. 

Depending on which version of the story you believe to be true, it is evident that Dr. Samuel Mudd hasn’t been favored by history. Various versions of the story have it that Dr. Mudd could be a conspirator in Lincoln’s assassination or a country doctor so innocent. It is believed that John Wilkes Booth, the assassinator of President Lincoln was treated by Dr. Samuel Mudd before fleeing away in 1865. Ever since, Mudd’s descendants have gone through thick and thin to try to clear the stains on Samuel Mudd’s name. 

The museum has several rooms with exhibits showcasing different histories and their relevance. Be sure to book a tour to this museum for an insight into America’s most important past. 

Chesapeake and Ohio Canal – 100 Miles or Biking Trail

This canal was built in the mid-18th century starting from Washington D.C. running all the way to Cumberland, cruising over 100 miles in distance. The canal has got plenty of fun activities to keep you and your crew jovial during the trip. 

There are paths running along the better part of the canal, presenting great opportunities to do cycling, hiking, or viewing the magnificent scenery. Several other important spots also surround this canal since it has a significant history behind it. 

During summer, boat tours are made available from Williamsport Visitor Center and Great Falls Visitor Center. You can take a boat tour to explore the picturesque views of this canal. Even though not so many people cover the length of the hiking trail, hiking a small portion of it will give you a memorable experience. Be sure to carry your camera to capture the fun moments and the beauty of nature around the canal. 

This is a perfect budget attraction in Maryland and for more such suggestions, check out our dedicated sampling.

The Ocean City – Sandy Beaches, Boardwalk, Ripley’s!

Ocean city - Ripley’s Believe It Not Museum & More!

Just like the name rings a bell, Ocean City is a beautiful city situated just by the edge of the sea. The fact that it’s along the Atlantic Ocean and it’s 10 miles long sandy beaches and plenty of recreational activities make it a good reason to pay this city a visit. 

The famous boardwalk on Ocean City’s southern end is a must-visit attraction that you wouldn’t want to miss. You can make stops along the boardwalk to watch live performances, play games, shop, and dine on the beach delicacies on offer. Don’t forget to make a stop at Ripley’s Believe It Not Museum for beautiful antiques and the world’s amazing displays. 

Patuxent Wine Trail – 7 Wineries & More!

Wine lovers, connoisseurs, and aspiring sommeliers pack your stuff and get set for this long road trip for amazing wine tasting experiences. A true wine enthusiast can visit up to 7 wineries in the Southern Maryland region along Patuxent Wine Trail. 

This trail winds through shoreline and farmlands, portraying beautiful sceneries to complement your wine tasting expedition. Among the wineries, you shouldn’t forget to pay a visit to those in Anne Arundel and Prince George’s counties. 

Wrapping up Maryland Road trip Destinations

Maryland, popularly nicknamed America in Miniature, has a little bit of everything, making it a perfect destination for anyone who seeks to explore the most within a limited timeframe. The coastal cities, stunning mountains, and maritime villages are just a few of the reasons you should have Maryland at the top of your road trip itinerary. You’ll definitely love its rich history as well, which shows that Maryland is deeply rooted in the past. 

We hope you plan a wonderful trip using our sampling of top Maryland road trip destinations. Book your vacation rental at to have the best road trip experience of your life! For any more information, fill the web form or feel free to give us a call.

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