3 Best Road Trip Vacations in Maryland

3 Best Road Trip Vacations in MarylandMaryland - the "Old Line State," packs a surprising punch within its compact borders. From the sandy shores of the Eastern Shore to the rolling hills of Western Maryland, this Chesapeake Bay gem offers a fantastic range of road trip options perfect for the whole family.

3 Best Road Trip Vacations in Maryland
3 Best Road Trip Vacations in Maryland

Maryland Road Trips: Chesapeake Charm, History, and Family-Friendly Adventures

Road Trip #1: Baltimore, Beach Towns, and a Touch of Wild West

  • Route: Baltimore – Ocean City – Assateague Island – Berlin - Baltimore
  • Distance: Approximately 300 miles
  • Duration: 4-6 days

Kick off your adventure in Baltimore, a vibrant harbor city with a revitalized Inner Harbor. Explore the top-notch National Aquarium, delve into maritime history at Fort McHenry, and grab a fresh crab cake at the bustling Lexington Market. Next, hit the iconic Ocean City boardwalk—a whirl of arcades, amusement park rides, and the quintessential smell of saltwater taffy.

Cross the bay to Assateague Island National Seashore, where wild ponies roam free amongst the sandy dunes and crashing waves. Hike the marshland trails, search for seashells, or simply spread a blanket and soak up the sun. Continue south to the charming small town of Berlin. This picturesque spot boasts antique shops, art galleries, and a dash of Wild West charm thanks to its annual cowboy festival.

Road Trip #2: Annapolis, the Chesapeake, and a Naval Academy Tour

  • Route: Annapolis – St. Michaels – Solomons Island – Chesapeake Beach – Annapolis
  • Distance: Approximately 150 miles
  • Duration: 2-4 days

Dig into Maryland's rich maritime roots in Annapolis, the state capital and sailing mecca. Embark on a narrated cruise, try your hand at sailing, or explore the campus of the renowned U.S. Naval Academy. Next, head east to St. Michaels, a quintessential Chesapeake Bay town. Delve into the Chesapeake Bay Maritime Museum, where you can build your toy boat or learn about the region's iconic oyster industry.

Venture south to Solomons Island, known for its Calvert Marine Museum. Get up close with river otters, learn about fossil discovery, or book a boat trip for potential dolphin sightings. Finish your trip with a stop at Chesapeake Beach. Enjoy the water park, stroll the boardwalk, or go fossil hunting along Calvert Cliffs.

Road Trip #3: History and Outdoor Adventures in Western Maryland

  • Route: Frederick – Harpers Ferry – Cumberland – Deep Creek Lake – Frederick
  • Distance: Approximately 300 miles
  • Duration: 4-6 days

Start in historic Frederick. Explore its charming downtown full of antique shops and restaurants, then journey to Harpers Ferry National Historical Park. This scenic town nestled at the Potomac and Shenandoah Rivers confluence is a Civil War history buff's dream. Next, head to Cumberland, the "Queen City" of the Appalachians. Ride the Western Maryland Scenic Railroad for stunning mountain views and learn about the area's role in the coal and rail industries.

Finish your trip with lakeside fun at Deep Creek Lake, Maryland's largest freshwater lake. Hike at Swallow Falls State Park, rent kayaks or paddleboards, or zipline through the treetops at Wisp Resort.

Additional Tips & Ideas for Your Journey

  • Best Season: Maryland's coastal areas are delightful in spring, summer, and fall. Consider the shoulder seasons for fewer crowds.
  • Local Delights: Indulge in fresh Maryland blue crabs, steamed and seasoned to perfection, and Smith Island Cake, the official state dessert with layers of deliciousness.
  • Unexpected Detours: Look for roadside farm stands, maritime festivals, and historic sites tucked away in Maryland's charming small towns.

Let Maryland's diverse landscapes and rich history fuel your next family adventure – the perfect road trip awaits!