Maryland may be small, but it packs a powerful punch of history, coastal beauty, outdoor adventure, charming towns, and culinary experiences. Whether you’re craving a coastal escape, a mountain retreat, or a dive into America’s heritage, a Maryland road trip offers something for every kind of traveler. In this blog, we’re laying out the perfect Maryland road trip itinerary ideal for a weekend trip to Maryland or a 3-4 day getaway.
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Things To Do in Maryland – Places to Visit in Maryland
Maryland is a hidden gem often overlooked in favor of its flashier neighbors like Washington, DC, or Pennsylvania. But if you’re seeking a compact, diverse destination for a road trip, Maryland is perfect. Why?
- You get a variety of landscapes: Atlantic coastlines, Chesapeake Bay, and Appalachian Mountains.
- It’s rich in colonial and Civil War history, especially in towns like Frederick and Annapolis.
- It’s compact enough to explore several diverse regions in just a few days.
Whether you’re a history buff, nature lover, or foodie, Maryland has the perfect coastal vibes with authentic vibes of the East Coast.
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Maryland Road Trip Itinerary Overview (4 Days)
From scenic drives to quaint harbor towns, this journey brings you the best places to visit in Maryland, including what to do, how to reach them, where to stay, and insider tips to make your trip unforgettable.
- Day 1: Baltimore
- Day 2: Annapolis
- Day 3: Chesapeake Bay & Eastern Shore (St. Michaels)
- Day 4: Western Maryland (Frederick & Catoctin Mountains)
How to Reach & Distance – Weekend Trip to Maryland
If you’re coming from nearby big cities:
- From Washington D.C. to Baltimore: ~40 miles (~1 hour by car via I-95 N)
- From Philadelphia to Annapolis: ~100 miles (~2 hours via I-95 S & US-50)
- From New York City to Baltimore: ~190 miles (~3.5 hours via I-95 S)
The best way to explore Maryland is by car, especially for a flexible Maryland road trip itinerary that lets you experience coastal and mountain charm. BWI Airport (Baltimore-Washington International) is the most convenient if you’re flying in.
Day 1: Baltimore – Culture & Waterfront Vibes
Baltimore, Maryland’s largest city, is a cultural hub that blends historic charm with modern vibrancy. It’s a must-visit on any Maryland road trip.
Things to do in Baltimore
- Inner Harbor: This scenic waterfront has attractions—visit the National Aquarium, hop on a harbor cruise, or relax at a waterfront café.
- Fells Point: A cobblestone-lined historic neighborhood with pubs and boutiques.
- Fort McHenry: The birthplace of the national anthem, this is a key stop for history lovers.
- Graffiti Alley: For a splash of urban color, this hidden gem is a local favorite for Instagram photos.
🛏️Overnight Stay in Baltimore – Sagamore Pendry Baltimore – Located right on the water in Fells Point with a rooftop pool and harbor views. Mid-range luxury with history built in.
Baltimore is a dynamic city where maritime history meets modern urban charm. It’s a perfect first stop to dive into Maryland’s cultural energy.
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Day 2: Annapolis – America’s Sailing Capital
Drive ~32 miles (45 mins) from Baltimore to Annapolis, the charming capital of Maryland, known for its maritime heritage and colonial architecture.
Annapolis’s colonial architecture, vibrant harbor, and nautical spirit enchant visitors. Home to the U.S. Naval Academy, it’s a blend of patriotism, history, and relaxed waterfront living. You’ll love walking the old town, exploring maritime museums, or setting sail on the Chesapeake Bay. It’s Maryland’s history and elegance rolled into one.
Things to do in Annapolis
- Historic Downtown: Stroll through quaint streets lined with Georgian brick buildings, cafés, and shops.
- U.S. Naval Academy Tour: Take a guided tour of this prestigious institution’s campus.
- Chesapeake Bay Cruises: Sail around the Bay and admire the historic skyline from the water.
- Maryland State House: The oldest state capitol still in use, rich in Revolutionary War history.
🛏️Overnight Stay in Annapolis – Graduate Annapolis – Retro-chic, affordable, and walking distance to the harbor.
Day 3: Chesapeake Bay & St. Michaels – Waterfront Escape
Cross the Chesapeake Bay Bridge (toll) and drive about 75 minutes (60 miles) to St. Michaels, a postcard-perfect town on the Eastern Shore of Maryland. This waterfront escape in Maryland is one of the most scenic parts of the state and perfect for a relaxing weekend trip to Maryland. This Chesapeake Bay village epitomizes small-town charm, offering boutique shops, food shacks, and scenic beauty.
Things to do in St. Michaels
- Chesapeake Bay Maritime Museum: Learn about the Bay’s nautical history with real boats and waterfront exhibits.
- Kayaking or Paddleboarding: Explore peaceful creeks and inlets on the Bay.
- Bike around town: Rent a bike and tour charming streets and nearby nature trails.
🛏️Overnight Stay in St. Michaels – St. Michaels Inn – Affordable, cozy, and close to all the town’s major sights.
St. Michaels brings peaceful Eastern Shore vibes and coastal relaxation to your itinerary.
Day 4: Frederick & Catoctin Mountains – History & Nature
Head west across the state for a change of scenery. Drive about 2.5 hours (~120 miles) to Frederick, a historic town nestled at the base of the Catoctin Mountains.
Frederick blends Civil War history with a buzzing arts scene and beautiful mountain backdrops. Its downtown area is filled with murals, antique shops, and outdoor cafés along Carroll Creek.
Things to do in Frederick & Surroundings
- Downtown Frederick: Beautiful 18th-century architecture, independent boutiques, and Carroll Creek Park—a walking path lined with public art and waterfront cafés.
- Monocacy National Battlefield: Step into Civil War history just outside town.
- Catoctin Mountain Park: Hike to Chimney Rock or Cunningham Falls—perfect for nature lovers.
- Visit Thurmont: The small town near Catoctin is also home to Camp David (not open to the public, but the nearby trails are stunning).
🛏️Overnight Stay in Frederick – 10 Clarke Bed & Breakfast – A Victorian mansion with stylish rooms and a homemade breakfast.
Frederick is an ideal stop to add nature and heritage to your Maryland road trip.
Tours to Book – Things To Do in Maryland Road Trip
For a more immersive experience, consider booking these tours:
- Baltimore Inner Harbor Cruise – Great way to view the skyline from the water.
- U.S. Naval Academy Guided Tour (Annapolis) – A fascinating military history tour.
- Chesapeake Bay Eco Kayak Tour (St. Michaels) – A peaceful paddle through the Eastern Shore’s waterscapes.
- Frederick Ghost Tour – Explore the haunted corners of the historic district at night.
Helpful Tips – Weekend trip to Maryland
- Toll Roads: Like the Chesapeake Bay Bridge, you’ll cross a few. EZ-Pass is handy.
- Weather: Spring and fall offer the best weather, which is pleasant and scenic.
- Packing Essentials: Bring walking shoes, layers (especially near the coast), and sunscreen.
- Parking: Urban areas like Baltimore and Annapolis can be tricky—use garages or park-and-walk zones.
FAQs – Places to Visit in Maryland
Q: Is 3-4 days enough for a Maryland road trip?
Yes! Maryland’s small size makes it ideal for a long weekend road trip. You can cover coastal towns, historical cities, and mountain hikes in just a few days.
Q: What’s the best time for a road trip to Maryland?
Late April to early June or September to October. You’ll get great weather and fewer crowds.
Q: Can I visit Maryland without a car?
You can reach cities like Baltimore or Annapolis by Amtrak or bus, but you need a car to explore Eastern Shore towns and mountain areas.
Q: Are Maryland’s small towns worth visiting?
Absolutely. Places like St. Michaels, Thurmont, and Frederick are rich in charm and ideal for a peaceful weekend getaway.
This Maryland road trip itinerary perfectly blends coastal serenity, historic intrigue, and natural beauty. Every stop adds unique flavor, from vibrant Baltimore to the scenic coves of St. Michaels, and the rolling hills near Frederick. It’s the kind of trip that offers both adventure and downtime, culinary experiences and cultural encounters. Whether you’re crafting Maryland road trip ideas for a romantic weekend, a family getaway, or a solo escape, this weekend getaway to Maryland gives you a little bit of everything without needing to drive far.
So grab your road trip playlist, roll down the windows, and hit the road—you’re in for an unforgettable Maryland road trip.\
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