Maryland is a small state with a big personality. Nestled on the East Coast, it offers everything from historic harbor towns to mountain getaways, vibrant cities, and miles of Chesapeake Bay shoreline. Whether you’re planning a weekend trip or mapping out a grand tour, this guide highlights the best cities, things to do, seasonal activities, accessibility, and more.

Top Cities to Visit and What to Do
Baltimore
Maryland’s largest city is famous for its historic waterfront, eclectic neighborhoods, and world-class museums. In Baltimore, don’t miss:
- Exploring the Inner Harbor with its shops, restaurants, and the National Aquarium
- Touring Fort McHenry, birthplace of the Star-Spangled Banner
- Visiting the American Visionary Art Museum and Walters Art Museum
- Sampling crab cakes at Lexington Market or Faidley’s Seafood

- Catching an Orioles baseball game at Camden Yards
- Walking historic Fell’s Point and Federal Hill neighborhoods
Baltimore is also known for its accessible museums and attractions, making it a welcoming city for all visitors (Baltimore.org).
Annapolis
Maryland’s capital is a charming blend of colonial history and nautical culture. Top things to do include:
- Touring the U.S. Naval Academy
- Strolling the Annapolis Historic District, full of 18th-century architecture
- Checking out the Maryland State House
- Dining at waterfront restaurants on Ego Alley
- Sailing or taking a cruise on the Chesapeake Bay

- Exploring the William Paca House and Hammond-Harwood House
- Enjoying live music and festivals along the waterfront
Late spring and early fall are ideal for visiting Annapolis, with mild weather and fewer crowds (Visit Maryland, NY Times).
Frederick
Set against a backdrop of rolling hills, Frederick is known for:
- A lively downtown filled with boutiques, breweries, and art galleries
- Touring Civil War sites like Monocacy National Battlefield
- Sampling local wines and farm-to-table restaurants
- Biking or hiking on the Frederick Watershed Trails

Ocean City
A classic beach town, Ocean City is perfect for:
- Relaxing on 10 miles of sandy beaches
- Walking the famous Boardwalk, lined with shops, rides, and eateries
- Visiting Trimper’s Rides and Jolly Roger Amusement Parks
- Fishing, kayaking, and parasailing on the bay
- Enjoying family-friendly events and summer fireworks
Ocean City has made major strides in accessibility, with accessible boardwalk entrances, beach wheelchairs, and inclusive events (Ocean City ADA).
Other Notable Destinations
- Bethesda & Silver Spring: Urban escapes with arts, theaters, and easy DC access
- Cumberland: Scenic railroad rides and outdoor adventures in western Maryland

- St. Michaels & Eastern Shore: Quaint harbor towns, wineries, and seafood festivals
A Brief History of Maryland
Founded as an English colony in 1634, Maryland played a pivotal role in America’s early history. The state was a battleground in the Revolutionary and Civil Wars, and its proximity to the nation’s capital has shaped its culture ever since. Baltimore’s Fort McHenry inspired the national anthem, while Annapolis served as the nation’s capital briefly after the Revolution. Maryland’s diverse landscapes and communities reflect centuries of change and adaptation.
Accessibility in Maryland
Maryland is dedicated to making travel accessible for all. Key features include:
- Accessible parking and entrances at most attractions
- Wheelchair-friendly museums, parks, and theaters
- Beach wheelchairs and accessible boardwalk access in Ocean City

- Mobility equipment rentals available in many cities
- Free national and state park passes for some people with disabilities (Visit Howard County, Visit Maryland)
The Best Time to Visit Maryland
- Spring (March–May): Cherry blossoms, mild weather, and outdoor festivals make this a favorite season.
- Summer (June–August): Perfect for beach trips to Ocean City, sailing on the bay, and crab feasts.
- Fall (September–November): Crisp air, colorful leaves in the mountains, and harvest festivals.
- Winter (December–February): Cozy up in historic inns, visit museums, and enjoy holiday events. Western Maryland offers skiing and snow tubing.
Seasonal Things To Do
Spring:
- Enjoy cherry blossoms in Baltimore and Annapolis
- Hike at Patapsco Valley State Park
- Attend spring festivals in Frederick and Silver Spring
Summer:
- Swim and sunbathe at Ocean City beaches
- Kayak, sail, or fish on the Chesapeake Bay
- Feast on Maryland blue crabs at local crab houses
Fall:
- Explore Catoctin Mountain Park and the Appalachian Trail for fall foliage
- Visit pumpkin patches and wineries on the Eastern Shore

- Tour historic battlefields in Antietam and Monocacy
Winter:
- Holiday shopping in downtown Frederick or Annapolis
- Ice skating in Baltimore’s Inner Harbor

- Ski or snowboard at Wisp Resort in western Maryland
Planning Your Trip
Maryland is easy to reach by air, car, or Amtrak. Major airports in Baltimore and near DC offer direct flights from across the U.S. Highways and scenic byways connect every region, and public transportation is robust in urban areas.
A Personal Note
Maryland’s charm lies in its variety. Whether you crave the bustle of city life, the quiet of the mountains, or the salty air of the coast, you’ll find it here—often just a short drive apart. From steamed crab feasts to historic streets and friendly neighborhoods, this state is full of surprises. I’d love to help you plan the perfect Maryland adventure.
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Let’s make your Maryland trip unforgettable!
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