Maryland Road Trips and Day Trips: Exploring the Old Line State

Road Trips in Maryland | Day Trips in Maryland

What Maryland is Known For: Chesapeake Bay, historical landmarks, and seafood.
Maryland’s Nickname: The Old Line State
Maryland’s Official Hobby: Jousting
Maryland’s Most Popular State Park: Assateague State Park | Berlin, Maryland

The old line state offers a variety of opportunities for Maryland road trips, from its stunning coastline and historic towns to scenic mountains and vibrant cities. Whether you’re exploring its natural beauty, rich history, or unique cuisine, Maryland promises a delightful and memorable journey.

Start your journey in Annapolis, the state’s capital known for its maritime history and charming downtown. Visit the United States Naval Academy, stroll through the historic Annapolis City Dock, and explore the Maryland State House. Don’t miss the Chesapeake Bay Maritime Museum for an in-depth look at the region’s nautical heritage.

Drive to the historic town of Frederick, known for its well-preserved 18th and 19th-century architecture. Explore the National Museum of Civil War Medicine, visit the Monocacy National Battlefield, and enjoy local dining at The Tasting Room, a local favorite.

Head to the picturesque town of St. Michaels, located on the Eastern Shore. Visit the Chesapeake Bay Maritime Museum, explore the charming downtown area filled with shops and restaurants, and take a scenic boat tour on the bay. Enjoy fresh seafood at The Crab Claw Restaurant, a beloved local eatery.

Don’t miss the scenic beauty of Assateague Island, known for its wild horses and pristine beaches. Explore the trails and beaches of Assateague State Park, and visit the nearby town of Berlin, which offers quaint shops, restaurants, and historic charm. Stay at the Atlantic Hotel for a taste of local hospitality.

Maryland’s scenic byways, such as the Chesapeake Country Scenic Byway, provide breathtaking views and lead to quaint small towns like Chestertown and Cambridge. In Chestertown, visit the Hynson-Ringgold House and enjoy a stroll along the waterfront. In Cambridge, explore the Harriet Tubman Underground Railroad Visitor Center and the charming downtown area.

Maryland Road Trip Checklist

Before you go on any road trip or day trip its advised you prepare and get the items you need including a phone charging cable, fix-a-flat tire repair, a cozzy neck pillow and more. This all inclusive guide is a day trip checklist to make sure if your road trip goes a little too long you are still covered. Make sure to check it out!

Top Road Trip Routes in Maryland

1. The Maritime Heritage Route

Route: US-50
Cities: Annapolis, St. Michaels, Easton
Attractions: United States Naval Academy, Chesapeake Bay Maritime Museum, Academy Art Museum

2. The Historical Journey

Route: I-70
Cities: Frederick, Hagerstown, Hancock
Attractions: National Museum of Civil War Medicine, Maryland Theatre, Fort Frederick State Park

3. The Eastern Shore Drive

Route: US-301
Cities: Chestertown, Cambridge, Salisbury
Attractions: Hynson-Ringgold House, Harriet Tubman Underground Railroad Visitor Center, Ward Museum of Wildfowl Art

4. The Coastal Adventure

Route: MD-611
Cities: Ocean City, Berlin, Assateague Island
Attractions: Ocean City Boardwalk, Atlantic Hotel, Assateague State Park

Best Times to Visit

Maryland experiences four distinct seasons, offering unique opportunities throughout the year.

• Spring (March to May): Ideal for enjoying mild weather, blooming flowers, and outdoor activities.
• Summer (June to August): Perfect for exploring state parks, attending festivals, and enjoying coastal activities, though it can be hot and humid.
• Fall (September to November): Offers cooler temperatures and stunning fall foliage, especially in the western mountains and along scenic byways.
• Winter (December to February): Best for indoor cultural activities and visiting museums, with mild winter weather compared to northern states.

Local Cuisine

Maryland’s culinary scene features fresh seafood and delicious regional dishes. Here are some must-try foods and restaurant recommendations in smaller towns:

• Maryland Crab Cakes: Try this state specialty at Faidley’s Seafood in Baltimore.
• Smith Island Cake: Enjoy a slice of this iconic cake at Smith Island Baking Company in Smith Island.
• Oysters: Visit The Narrows Restaurant in Grasonville for fresh Chesapeake Bay oysters.
• Pit Beef Sandwich: Savor this local favorite at Chaps Pit Beef in Baltimore.
• Old Bay Seasoned Fries: Try this Maryland twist on fries at Thrasher’s French Fries in Ocean City.

Most Unique Stays in Maryland

1. The Inn at Perry Cabin
   • Location: St. Michaels, Maryland
   • What makes it unique?: A luxurious waterfront resort offering elegant rooms, a full-service spa, and stunning views of the Miles River.
2. The Historic Inns of Annapolis
   • Location: Annapolis, Maryland
   • What makes it unique?: A collection of three historic inns offering charming accommodations, rich history, and a prime location in downtown Annapolis.
3. C&O Canal Lockhouses
   • Location: Various locations along the C&O Canal, Maryland
   • What makes it unique?: Historic lockhouses offering a unique stay experience along the scenic C&O Canal, perfect for history enthusiasts and nature lovers.
4. The Atlantic Hotel
   • Location: Berlin, Maryland
   • What makes it unique?: A historic hotel offering charming rooms, a cozy atmosphere, and a central location in the heart of Berlin.
5. The Kent Manor Inn
   • Location: Stevensville, Maryland
   • What makes it unique?: A historic waterfront inn offering elegant accommodations, beautiful gardens, and easy access to Chesapeake Bay activities.

Travel Tips

1. Explore Local Festivals: Maryland hosts numerous festivals, such as the Maryland Renaissance Festival in Crownsville and the Chesapeake Bay Balloon Festival in Easton. Plan your trip around these events for a unique experience.
2. Scenic Byways: Take advantage of Maryland’s scenic byways for a leisurely drive through picturesque landscapes and charming small towns.
3. Historic Sites: Many of Maryland’s historic sites offer guided tours. Check the schedules and book in advance to make the most of your visit.
4. Weather Preparedness: Maryland weather can vary greatly. Pack layers and be prepared for changing conditions, especially if traveling through different regions of the state.